Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles
We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp3)–NiX intermediates with arylzinc reagents. This approach utilizes a readily removable imine as a coordinating group that plays a dual role of intercepting oxidative addition species de...
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| Published in | Journal of the American Chemical Society Vol. 139; no. 31; pp. 10653 - 10656 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
09.08.2017
Amer Chemical Soc American Chemical Society (ACS) |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0002-7863 1520-5126 1520-5126 |
| DOI | 10.1021/jacs.7b06340 |
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| Abstract | We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp3)–NiX intermediates with arylzinc reagents. This approach utilizes a readily removable imine as a coordinating group that plays a dual role of intercepting oxidative addition species derived from aryl halides and triflates to promote Heck carbometalation and stabilizing the Heck C(sp3)–NiX intermediates as transient metallacycles to suppress β-hydride elimination and facilitate transmetalation/reductive elimination steps. This method affords diversely substituted 1,1,2-triarylethyl products that occur as structural motifs in various natural products. |
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| AbstractList | We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp
)-NiX intermediates with arylzinc reagents. This approach utilizes a readily removable imine as a coordinating group that plays a dual role of intercepting oxidative addition species derived from aryl halides and triflates to promote Heck carbometalation and stabilizing the Heck C(sp
)-NiX intermediates as transient metallacycles to suppress β-hydride elimination and facilitate transmetalation/reductive elimination steps. This method affords diversely substituted 1,1,2-triarylethyl products that occur as structural motifs in various natural products. We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp3)–NiX intermediates with arylzinc reagents. This approach utilizes a readily removable imine as a coordinating group that plays a dual role of intercepting oxidative addition species derived from aryl halides and triflates to promote Heck carbometalation and stabilizing the Heck C(sp3)–NiX intermediates as transient metallacycles to suppress β-hydride elimination and facilitate transmetalation/reductive elimination steps. This method affords diversely substituted 1,1,2-triarylethyl products that occur as structural motifs in various natural products. We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp3)-NiX intermediates with arylzinc reagents. This approach utilizes a readily removable imine as a coordinating group that plays a dual role of intercepting oxidative addition species derived from aryl halides and triflates to promote Heck carbometalation and stabilizing the Heck C(sp3)-NiX intermediates as transient metallacycles to suppress β-hydride elimination and facilitate transmetalation/reductive elimination steps. This method affords diversely substituted 1,1,2-triarylethyl products that occur as structural motifs in various natural products.We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp3)-NiX intermediates with arylzinc reagents. This approach utilizes a readily removable imine as a coordinating group that plays a dual role of intercepting oxidative addition species derived from aryl halides and triflates to promote Heck carbometalation and stabilizing the Heck C(sp3)-NiX intermediates as transient metallacycles to suppress β-hydride elimination and facilitate transmetalation/reductive elimination steps. This method affords diversely substituted 1,1,2-triarylethyl products that occur as structural motifs in various natural products. We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp(3))-NiX intermediates with arylzinc reagents. This approach utilizes a readily removable imine as a coordinating group that plays a dual role of intercepting oxidative addition species derived from aryl halides and triflates to promote Heck carbometalation and stabilizing the Heck C(sp(3))-NiX intermediates as transient metallacycles to suppress beta-hydride elimination and facilitate transmetalation/reductive elimination steps. This method affords diversely substituted 1,1,2-triarylethyl products that occur as structural motifs in various natural products. We disclose a strategy for Ni-catalyzed regioselective dicarbofunctionalization of olefins in styrene derivatives by intercepting Heck C(sp3)-NiX intermediates with arylzinc reagents. This approach utilizes a readily removable imine as a coordinating group that plays a dual role of intercepting oxidative addition species derived from aryl halides and triflates to promote Heck carbometallation, and stabilizing the Heck C(sp3)-NiX intermediates as transient metallacycles to suppress β-hydride elimination and facilitate transmetalation/reductive elimination steps. This method affords diversely-substituted 1,1,2-riarylethyl products that occur as structural motifs in various natural products. We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp³)–NiX intermediates with arylzinc reagents. This approach utilizes a readily removable imine as a coordinating group that plays a dual role of intercepting oxidative addition species derived from aryl halides and triflates to promote Heck carbometalation and stabilizing the Heck C(sp³)–NiX intermediates as transient metallacycles to suppress β-hydride elimination and facilitate transmetalation/reductive elimination steps. This method affords diversely substituted 1,1,2-triarylethyl products that occur as structural motifs in various natural products. |
| Author | Dhungana, Roshan K KC, Shekhar Giri, Ramesh Basnet, Prakash Shrestha, Bijay Thapa, Surendra Sears, Jeremiah M |
| AuthorAffiliation | Advanced Materials Laboratory The University of New Mexico Department of Chemistry & Chemical Biology Sandia National Laboratory |
| AuthorAffiliation_xml | – name: Department of Chemistry & Chemical Biology – name: Sandia National Laboratory – name: The University of New Mexico – name: Advanced Materials Laboratory |
| Author_xml | – sequence: 1 givenname: Bijay surname: Shrestha fullname: Shrestha, Bijay organization: The University of New Mexico – sequence: 2 givenname: Prakash surname: Basnet fullname: Basnet, Prakash organization: The University of New Mexico – sequence: 3 givenname: Roshan K surname: Dhungana fullname: Dhungana, Roshan K organization: The University of New Mexico – sequence: 4 givenname: Shekhar surname: KC fullname: KC, Shekhar organization: The University of New Mexico – sequence: 5 givenname: Surendra surname: Thapa fullname: Thapa, Surendra organization: The University of New Mexico – sequence: 6 givenname: Jeremiah M surname: Sears fullname: Sears, Jeremiah M organization: Advanced Materials Laboratory – sequence: 7 givenname: Ramesh orcidid: 0000-0002-8993-9131 surname: Giri fullname: Giri, Ramesh email: rgiri@unm.edu organization: The University of New Mexico |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28737904$$D View this record in MEDLINE/PubMed https://www.osti.gov/servlets/purl/1399511$$D View this record in Osti.gov |
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| Cites_doi | 10.1021/acs.orglett.6b02154 10.1021/ja045047p 10.1002/chem.201200190 10.1002/open.201100010 10.1002/anie.201606458 10.1002/anie.200900218 10.1055/s-2003-42082 10.1021/ol301539p 10.1021/ja304344h 10.1002/anie.201308391 10.1002/anie.201607976 10.1021/ja209235d 10.1021/ja0100423 10.1021/ja2084509 10.1021/jacs.5b08734 10.1055/s-2005-871541 10.1021/ol200536h 10.1021/ja046810i 10.1021/jacs.5b10176 10.1021/acs.orglett.7b00794 10.1021/ja509056j 10.1021/jo1018188 10.1021/acs.orglett.7b01036 10.1002/ejoc.201403511 10.1021/jo960617s 10.1021/jacs.7b01922 10.1016/S0040-4039(00)96556-0 10.1002/anie.201606955 10.1002/anie.200702528 10.1021/acs.orglett.7b00940 10.1002/anie.200500195 10.1002/adsc.200404041 10.1021/ol303003g 10.1021/ol1009703 10.1021/ja201358b 10.1021/ja412881j 10.1021/jacs.6b09170 10.1021/ol502279u 10.1002/anie.201108350 10.1021/ol0356643 10.1021/jacs.7b03195 10.1021/ol1009575 10.1021/ja00437a018 10.1021/ja052099l 10.1021/ja002582q 10.1021/ja3116718 10.1021/ja806183r 10.1016/S0968-0896(01)00038-4 10.1016/S0010-8545(96)90182-4 10.1021/cr00026a008 10.1021/acs.joc.5b01126 10.1016/S0040-4020(97)00754-0 10.1021/jo00309a020 10.1039/c39950000295 10.1021/ol048620i 10.1126/science.aaf6123 10.1021/ol4023358 10.1021/ja072571y 10.1021/ja5026485 10.1021/ja500706v 10.1021/jacs.6b09596 10.1016/j.tet.2008.06.099 10.1002/anie.201605744 10.1016/0022-328X(88)80484-4 10.1007/3418_2007_063 |
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| Copyright | Copyright © 2017 American Chemical Society |
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| Keywords | 3-COMPONENT COUPLING REACTION CARBON-MONOXIDE RADICAL CYCLIZATION QUATERNARY STEREOCENTERS STEREOSELECTIVE-SYNTHESIS UNACTIVATED OLEFINS TERMINAL ALKENES ARYLBORONIC ACIDS ALKYL-HALIDES CARBOXYLIC-ACIDS |
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| PublicationDate | 2017-08-09 |
| PublicationDateYYYYMMDD | 2017-08-09 |
| PublicationDate_xml | – month: 08 year: 2017 text: 2017-08-09 day: 09 |
| PublicationDecade | 2010 |
| PublicationPlace | WASHINGTON |
| PublicationPlace_xml | – name: WASHINGTON – name: United States |
| PublicationTitle | Journal of the American Chemical Society |
| PublicationTitleAbbrev | J AM CHEM SOC |
| PublicationTitleAlternate | J. Am. Chem. Soc |
| PublicationYear | 2017 |
| Publisher | American Chemical Society Amer Chemical Soc American Chemical Society (ACS) |
| Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc – name: American Chemical Society (ACS) |
| References | ref17/cit17b ref17/cit17c ref17/cit17d ref17/cit17e ref17/cit17a ref13/cit13a ref13/cit13b ref13/cit13c ref12/cit12b ref12/cit12a ref2/cit2c ref2/cit2b ref2/cit2a ref1/cit1a ref1/cit1b ref5/cit5b ref5/cit5c ref5/cit5a ref16/cit16c ref16/cit16b ref16/cit16a ref7/cit7g ref16/cit16g ref7/cit7f ref16/cit16f ref7/cit7e ref16/cit16e ref7/cit7d ref16/cit16d ref3/cit3b ref11/cit11c ref3/cit3c ref11/cit11b ref16/cit16j ref16/cit16i ref3/cit3a ref7/cit7h ref16/cit16h ref3/cit3d ref11/cit11a ref3/cit3e ref7/cit7c ref7/cit7b ref7/cit7a ref5/cit5d ref9/cit9c ref9/cit9b ref9/cit9a ref8/cit8a ref10/cit10a ref10/cit10b ref8/cit8b ref10/cit10c ref9/cit9e ref9/cit9d ref4/cit4a ref4/cit4b ref14/cit14a ref14/cit14c ref14/cit14b ref20/cit20a ref20/cit20b ref6/cit6a ref6/cit6b ref6/cit6c Wakabayashi, K (WOS:000169041300035) 2001; 123 Urkalan, KB (WOS:000265465200029) 2009; 48 Liu, XL (WOS:000359393500024) 2015; 80 MCDERMOTT, JX (WOS:A1976CG22700018) 1976; 98 Liu, C (WOS:000223433700029) 2004; 126 McMahon, CM (WOS:000381847500054) 2016; 18 Wu, X (WOS:000363916600010) 2015; 137 ISHIYAMA, T (WOS:A1995QG93500002) 1995 Fusano, A (WOS:000289187200057) 2011; 13 Vaupel, A (WOS:A1996VE27200015) 1996; 61 Kim, JG (WOS:000351054500017) 2015; 2015 Liu, Z (WOS:000388913600007) 2016; 138 Matsubara, R (WOS:000297662800002) 2011; 133 Stokes, BJ (WOS:000341344600081) 2014; 16 Perez-Gomez, M (WOS:000387028000034) 2016; 55 Werner, EW (WOS:000278616800044) 2010; 12 Terao, J (WOS:000223438200004) 2004; 346 Talbot, EPA (WOS:000333435500003) 2014; 136 Balme, G. (000407540200016.2) 2003; 2003 Guo, HC (WOS:000234604400006) 2006; 45 Tasker, SZ (WOS:000330680400019) 2014; 53 Phapale, VB (WOS:000251354300008) 2007; 46 Dhungana, RK (WOS:000400123600055) 2017; 19 Iwamoto, H (WOS:000402023500040) 2017; 19 Liu, C (WOS:000302348200022) 2012; 51 Xue, WC (WOS:000387095000015) 2016; 138 Qin, T. (000407540200016.39) 2016; 352 Garcia-Dominguez, A (WOS:000402498500014) 2017; 139 Saini, V. (000407540200016.41) 2012; 134 Gogsig, TM (WOS:000301084200079) 2012; 134 Desrosiers, JN (WOS:000384713100038) 2016; 55 Fournet, G. (000407540200016.8) 1987; 28 Cavell, KJ (WOS:A1996VU09800009) 1996; 155 Yan, CS (WOS:000303497100029) 2012; 18 You, W (WOS:000366004700007) 2015; 137 LEBEDEV, SA (WOS:A1988M967300013) 1988; 344 ANDERSSON, CM (WOS:A1990EF32200020) 1990; 55 Yahiaoui, S (WOS:000289187300004) 2011; 76 Snyder, SA (WOS:000264792100040) 2009; 131 Rubin, VN (WOS:000169404600021) 2001; 9 Nakamura, M (WOS:000230448500037) 2005 Trejos, A (WOS:000258841100022) 2008; 64 Oestreich, M (WOS:000266964700007) 2007; 24 Trejos, A (WOS:000328606600008) 2012; 1 Seashore-Ludlow, B. (000407540200016.44) 2012; 14 Tanaka, D (WOS:000230700700049) 2005; 127 Saini, V (WOS:000326320200024) 2013; 15 Burke, BJ (WOS:000225910400040) 2004; 126 Seashore-Ludlow, B (WOS:000281180700002) 2010; 12 Cong, H (WOS:000332922600020) 2014; 136 Kuang, ZJ (WOS:000402023500062) 2017; 19 Mizutani, K (WOS:000185901600047) 2003; 5 Tang, J (WOS:000383642300063) 2016; 55 Grigg, R (WOS:A1997XR68800023) 1997; 53 You, W (WOS:000343686500025) 2014; 136 IQBAL, J (WOS:A1994NG03100008) 1994; 94 Neufeldt, SR (WOS:000313156400013) 2013; 15 Gu, JW (WOS:000384713700020) 2016; 55 Machotta, AB (WOS:000250819200031) 2007; 129 Standley, EA (WOS:000314492500063) 2013; 135 Itami, K (WOS:000224349100011) 2004; 6 Harris, MR (WOS:000337014400011) 2014; 136 Thapa, S (WOS:000400321500017) 2017; 139 Itami, K (WOS:000165696900040) 2000; 122 Liao, LY (WOS:000290358200045) 2011; 133 |
| References_xml | – ident: ref7/cit7a doi: 10.1021/acs.orglett.6b02154 – ident: ref13/cit13b doi: 10.1021/ja045047p – ident: ref3/cit3e doi: 10.1002/chem.201200190 – ident: ref6/cit6c doi: 10.1002/open.201100010 – ident: ref12/cit12a doi: 10.1002/anie.201606458 – ident: ref6/cit6b doi: 10.1002/anie.200900218 – ident: ref2/cit2b doi: 10.1055/s-2003-42082 – ident: ref4/cit4a doi: 10.1021/ol301539p – ident: ref10/cit10a doi: 10.1021/ja304344h – ident: ref16/cit16c doi: 10.1002/anie.201308391 – ident: ref7/cit7g doi: 10.1002/anie.201607976 – ident: ref16/cit16a doi: 10.1021/ja209235d – ident: ref3/cit3d doi: 10.1021/ja0100423 – ident: ref16/cit16g doi: 10.1021/ja2084509 – ident: ref9/cit9b doi: 10.1021/jacs.5b08734 – ident: ref3/cit3c doi: 10.1055/s-2005-871541 – ident: ref7/cit7d doi: 10.1021/ol200536h – ident: ref7/cit7c doi: 10.1021/ja046810i – ident: ref5/cit5b doi: 10.1021/jacs.5b10176 – ident: ref2/cit2a doi: 10.1021/acs.orglett.7b00794 – ident: ref5/cit5c doi: 10.1021/ja509056j – ident: ref6/cit6a doi: 10.1021/jo1018188 – ident: ref9/cit9c doi: 10.1021/acs.orglett.7b01036 – ident: ref3/cit3a doi: 10.1002/ejoc.201403511 – ident: ref7/cit7b doi: 10.1021/jo960617s – ident: ref5/cit5a doi: 10.1021/jacs.7b01922 – ident: ref2/cit2c doi: 10.1016/S0040-4039(00)96556-0 – ident: ref16/cit16j doi: 10.1002/anie.201606955 – ident: ref3/cit3b doi: 10.1002/anie.200702528 – ident: ref11/cit11c doi: 10.1021/acs.orglett.7b00940 – ident: ref17/cit17a – ident: ref1/cit1a doi: 10.1002/anie.200500195 – ident: ref9/cit9d doi: 10.1002/adsc.200404041 – ident: ref14/cit14c doi: 10.1021/ol303003g – ident: ref7/cit7e doi: 10.1021/ol1009703 – ident: ref9/cit9a doi: 10.1021/ja201358b – ident: ref14/cit14b doi: 10.1021/ja412881j – ident: ref14/cit14a doi: 10.1021/jacs.6b09170 – ident: ref12/cit12b doi: 10.1021/ol502279u – ident: ref16/cit16e doi: 10.1002/anie.201108350 – ident: ref9/cit9e doi: 10.1021/ol0356643 – ident: ref11/cit11a doi: 10.1021/jacs.7b03195 – ident: ref10/cit10b doi: 10.1021/ol1009575 – ident: ref13/cit13a doi: 10.1021/ja00437a018 – ident: ref13/cit13c doi: 10.1021/ja052099l – ident: ref17/cit17d doi: 10.1021/ja002582q – ident: ref16/cit16b doi: 10.1021/ja3116718 – ident: ref20/cit20a doi: 10.1021/ja806183r – ident: ref20/cit20b doi: 10.1016/S0968-0896(01)00038-4 – ident: ref8/cit8a doi: 10.1016/S0010-8545(96)90182-4 – ident: ref8/cit8b doi: 10.1021/cr00026a008 – ident: ref7/cit7h doi: 10.1021/acs.joc.5b01126 – ident: ref4/cit4b doi: 10.1016/S0040-4020(97)00754-0 – ident: ref17/cit17e doi: 10.1021/jo00309a020 – ident: ref7/cit7f doi: 10.1039/c39950000295 – ident: ref17/cit17c doi: 10.1021/ol048620i – ident: ref1/cit1b doi: 10.1126/science.aaf6123 – ident: ref10/cit10c doi: 10.1021/ol4023358 – ident: ref16/cit16i doi: 10.1021/ja072571y – ident: ref16/cit16d doi: 10.1021/ja5026485 – ident: ref5/cit5d doi: 10.1021/ja500706v – ident: ref11/cit11b doi: 10.1021/jacs.6b09596 – ident: ref16/cit16h doi: 10.1016/j.tet.2008.06.099 – ident: ref17/cit17b doi: 10.1002/anie.201605744 – ident: ref16/cit16f doi: 10.1016/0022-328X(88)80484-4 – volume: 19 start-page: 2154 year: 2017 ident: WOS:000400123600055 article-title: Pd-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Unactivated Olefins by a Heck Reaction/Enolate Cyclization Cascade publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.7b00794 – volume: 28 start-page: 4533 year: 1987 ident: 000407540200016.8 publication-title: Tetrahedron Lett. – volume: 19 start-page: 2702 year: 2017 ident: WOS:000402023500062 article-title: Pd-Catalyzed Regioselective 1,2-Difunctionalization of Vinylarenes with Alkenyl Triflates and Aryl Boronic Acids at Ambient Temperature publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.7b01036 – volume: 155 start-page: 209 year: 1996 ident: WOS:A1996VU09800009 article-title: Recent fundamental studies on migratory insertion into metal-carbon bonds publication-title: COORDINATION CHEMISTRY REVIEWS – volume: 19 start-page: 2614 year: 2017 ident: WOS:000402023500040 article-title: Copper(I)-Catalyzed Stereo- and Chemoselective Borylative Radical Cyclization of Alkyl Halides Bearing an Alkene Moiety publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.7b00940 – volume: 64 start-page: 8746 year: 2008 ident: WOS:000258841100022 article-title: Stereoselective Heck arylation of a functionalized cyclopentenyl ether using (S)-N-methyl-pyrrolidine as the stereochemical controller publication-title: TETRAHEDRON doi: 10.1016/j.tet.2008.06.099 – volume: 136 start-page: 14730 year: 2014 ident: WOS:000343686500025 article-title: Diarylation of Alkenes by a Cu-Catalyzed Migratory Insertion/Cross-Coupling Cascade publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja509056j – volume: 134 start-page: 443 year: 2012 ident: WOS:000301084200079 article-title: Mild and Efficient Nickel-Catalyzed Heck Reactions with Electron-Rich Olefins publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja2084509 – volume: 138 start-page: 15122 year: 2016 ident: WOS:000388913600007 article-title: beta,gamma-Vicinal Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Directed Nucleopalladation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.6b09170 – volume: 61 start-page: 5743 year: 1996 ident: WOS:A1996VE27200015 article-title: Stereoselective synthesis of heterocyclic zinc reagents via a nickel-catalyzed radical cyclization publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 133 start-page: 5784 year: 2011 ident: WOS:000290358200045 article-title: A Palladium-Catalyzed Three-Component Cross-Coupling of Conjugated Dienes or Terminal Alkenes with Vinyl Triflates and Boronic Acids publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja201358b – volume: 80 start-page: 7547 year: 2015 ident: WOS:000359393500024 article-title: Palladium-Catalyzed Heck-type Domino Cyclization and Carboxylation to Synthesize Carboxylic Acids by Utilizing Chloroform as the Carbon Monoxide Source publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.5b01126 – volume: 76 start-page: 2433 year: 2011 ident: WOS:000289187300004 article-title: Chelation-Mediated Palladium(II)-Catalyzed Domino Heck-Mizoroki/Suzuki-Miyaura Reactions Using Arylboronic Acids: Increasing Scope and Mechanistic Understanding publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo1018188 – volume: 131 start-page: 1753 year: 2009 ident: WOS:000264792100040 article-title: Total Synthesis of Diverse Carbogenic Complexity within the Resveratrol Class from a Common Building Block publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja806183r – volume: 5 start-page: 3959 year: 2003 ident: WOS:000185901600047 article-title: Cobalt-catalyzed three-component coupling reaction of alkyl halides, 1,3-dienes, and trimethylsilylmethylmagnesium chloride publication-title: ORGANIC LETTERS doi: 10.1021/ol0356643 – volume: 15 start-page: 5008 year: 2013 ident: WOS:000326320200024 article-title: Pd(0)-Catalyzed 1,1-Diarylation of Ethylene and Allylic Carbonates publication-title: ORGANIC LETTERS doi: 10.1021/ol4023358 – volume: 1 start-page: 49 year: 2012 ident: WOS:000328606600008 article-title: Development of Stereocontrolled Palladium(II)-Catalyzed Domino Heck/Suzuki beta,alpha-Diarylation Reactions with Chelating Vinyl Ethers and Arylboronic Acids publication-title: CHEMISTRYOPEN doi: 10.1002/open.201100010 – volume: 18 start-page: 4148 year: 2016 ident: WOS:000381847500054 article-title: Manganese-Catalyzed Carboacylations of Alkenes with Alkyl Iodides publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.6b02154 – volume: 136 start-page: 4101 year: 2014 ident: WOS:000333435500003 article-title: Asymmetric Palladium-Catalyzed Directed Intermolecular Fluoroarylation of Styrenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja412881j – volume: 45 start-page: 354 year: 2006 ident: WOS:000234604400006 article-title: Catalytic asymmetric tandem transformations triggered by conjugate additions publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200500195 – volume: 55 start-page: 14387 year: 2016 ident: WOS:000387028000034 article-title: Trapping sigma-Alkyl-Palladium(II) Intermediates with Arynes Encompassing Intramolecular C-H Activation: Spirobiaryls through Pd-Catalyzed Cascade Reactions publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201607976 – volume: 14 start-page: 3858 year: 2012 ident: 000407540200016.44 publication-title: Org. Lett. – volume: 122 start-page: 12013 year: 2000 ident: WOS:000165696900040 article-title: Highly efficient carbopalladation across vinylsilane: Dual role of the 2-PyMe2Si group as a directing group and as a phase tag publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja002582q – volume: 139 start-page: 5700 year: 2017 ident: WOS:000400321500017 article-title: Copper-Catalyzed Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b01922 – volume: 2003 start-page: 2115 year: 2003 ident: 000407540200016.2 publication-title: Synthesis – volume: 346 start-page: 905 year: 2004 ident: WOS:000223438200004 article-title: Nickel-catalyzed regioselective three component coupling reaction of alkyl halides, butadienes, and Ar-M (M = MgX, ZnX) publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.200404041 – volume: 123 start-page: 5374 year: 2001 ident: WOS:000169041300035 article-title: Cobalt-catalyzed tandem radical cyclization and cross-coupling reaction: Its application to benzyl-substituted heterocycles publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0100423 – volume: 98 start-page: 6521 year: 1976 ident: WOS:A1976CG22700018 article-title: THERMAL-DECOMPOSITION OF BIS(PHOSPHINE)PLATINUM(II) METALLOCYCLES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 135 start-page: 1585 year: 2013 ident: WOS:000314492500063 article-title: Simplifying Nickel(0) Catalysis: An Air-Stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja3116718 – volume: 127 start-page: 10323 year: 2005 ident: WOS:000230700700049 article-title: On the mechanism of the palladium(II)-catalyzed decarboxylative olefination of arene carboxylic acids. Crystallographic characterization of non-phosphine palladium(II) intermediates and observation of their stepwise transformation in Heck-like processes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja052099l – volume: 12 start-page: 2848 year: 2010 ident: WOS:000278616800044 article-title: Pd-II-Catalyzed Oxidative 1,1-Diarylation of Terminal Olefins publication-title: ORGANIC LETTERS doi: 10.1021/ol1009575 – volume: 55 start-page: 11296 year: 2016 ident: WOS:000383642300063 article-title: Branched Arylalkenes from Cinnamates: Selectivity Inversion in Heck Reactions by Carboxylates as Deciduous Directing Groups publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201605744 – volume: 9 start-page: 1579 year: 2001 ident: WOS:000169404600021 article-title: Identification of new triarylethylene oxyalkanoic acid analogues as bone selective estrogen mimetics publication-title: BIOORGANIC & MEDICINAL CHEMISTRY – volume: 6 start-page: 3695 year: 2004 ident: WOS:000224349100011 article-title: Stereoselective synthesis of multisubstituted butadienes through directed Mizoroki-Heck reaction and homocoupling reaction of vinyl(2-pyridyl)silane publication-title: ORGANIC LETTERS doi: 10.1021/ol048620i – volume: 18 start-page: 6039 year: 2012 ident: WOS:000303497100029 article-title: Nickel-Mediated Inter- and Intramolecular Reductive Cross-Coupling of Unactivated Alkyl Bromides and Aryl Iodides at Room Temperature publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201200190 – volume: 12 start-page: 3732 year: 2010 ident: WOS:000281180700002 article-title: Domino Carbopalladation-Carbonylation: Generating Quaternary Stereocenters while Controlling beta-Hydride Elimination publication-title: ORGANIC LETTERS doi: 10.1021/ol1009703 – volume: 133 start-page: 19020 year: 2011 ident: WOS:000297662800002 article-title: Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja209235d – volume: 24 start-page: 169 year: 2007 ident: WOS:000266964700007 article-title: Directed Mizoroki-Heck Reactions publication-title: DIRECTED METALLATION doi: 10.1007/3418_2007_063 – volume: 51 start-page: 3638 year: 2012 ident: WOS:000302348200022 article-title: Nickel-Catalyzed Heck-Type Alkenylation of Secondary and Tertiary a-Carbonyl Alkyl Bromides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201108350 – volume: 129 start-page: 13455 year: 2007 ident: WOS:000250819200031 article-title: Oxygen donor-mediated equilibration of diastereomeric alkene-Palladium(II) intermediates in enantioselective desymmetrizing heck cyclizations publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja072571y – volume: 53 start-page: 1858 year: 2014 ident: WOS:000330680400019 article-title: Nickel-Catalyzed Mizoroki-Heck Reaction of Aryl Sulfonates and Chlorides with Electronically Unbiased Terminal Olefins: High Selectivity for Branched Products publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201308391 – volume: 139 start-page: 6835 year: 2017 ident: WOS:000402498500014 article-title: Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b03195 – volume: 137 start-page: 14578 year: 2015 ident: WOS:000366004700007 article-title: Catalytic Enantioselective Diarylation of Alkenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.5b10176 – volume: 55 start-page: 11921 year: 2016 ident: WOS:000384713100038 article-title: Construction of Quaternary Stereocenters by Nickel-Catalyzed Heck Cyclization Reactions publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201606955 – volume: 137 start-page: 13476 year: 2015 ident: WOS:000363916600010 article-title: Enantioselective 1,2-Difunctionalization of Dienes Enabled by Chiral Palladium Complex-Catalyzed Cascade Arylation/Allylic Alkylation Reaction publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.5b08734 – volume: 46 start-page: 8790 year: 2007 ident: WOS:000251354300008 article-title: Ni-catalyzed cascade formation of C(sp(3))-C(sp(3)) bonds by cyclization and cross-coupling reactions of iodoalkanes with alkyl zinc halides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200702528 – volume: 126 start-page: 16820 year: 2004 ident: WOS:000225910400040 article-title: Enantioselective synthesis of six-membered palladacycles having metal-bound stereogenic carbons: Isolation and reactivity of palladacycles containing readily accessible beta-hydrogens publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja045047p – volume: 53 start-page: 11803 year: 1997 ident: WOS:A1997XR68800023 article-title: Palladium catalysed tandem cyclisation-anion capture processes .3. Organoboron anion transfer agents publication-title: TETRAHEDRON – volume: 136 start-page: 7825 year: 2014 ident: WOS:000337014400011 article-title: Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja5026485 – volume: 48 start-page: 3146 year: 2009 ident: WOS:000265465200029 article-title: Palladium-Catalyzed Oxidative Intermolecular Difunctionalization of Terminal Alkenes with Organostannanes and Molecular Oxygen publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200900218 – volume: 134 start-page: 11372 year: 2012 ident: 000407540200016.41 publication-title: J. Am. Chem. Soc. – volume: 15 start-page: 46 year: 2013 ident: WOS:000313156400013 article-title: Asymmetric Chiral Ligand-Directed Alkene Dioxygenation publication-title: ORGANIC LETTERS doi: 10.1021/ol303003g – volume: 55 start-page: 12270 year: 2016 ident: WOS:000384713700020 article-title: Tandem Difluoroalkylation-Arylation of Enamides Catalyzed by Nickel publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201606458 – start-page: 1794 year: 2005 ident: WOS:000230448500037 article-title: Iron-catalyzed chemoselective cross-coupling of primary and secondary alkyl halides with arylzinc reagents publication-title: SYNLETT doi: 10.1055/s-2005-871541 – start-page: 295 year: 1995 ident: WOS:A1995QG93500002 article-title: SYNTHESIS OF KETONES FROM IODOALKENES, CARBON-MONOXIDE AND 9-ALKYL-9-BORABICYCLO[3,3,1]NONANE DERIVATIVES VIA A RADICAL CYCLIZATION AND PALLADIUM-CATALYZED CARBONYLATIVE CROSS-COUPLING SEQUENCE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS – volume: 94 start-page: 519 year: 1994 ident: WOS:A1994NG03100008 article-title: TRANSITION METAL-PROMOTED FREE-RADICAL REACTIONS IN ORGANIC-SYNTHESIS - THE FORMATION OF CARBON-CARBON BONDS publication-title: CHEMICAL REVIEWS – volume: 16 start-page: 4666 year: 2014 ident: WOS:000341344600081 article-title: A Palladium-Catalyzed Three-Component-Coupling Strategy for the Differential Vicinal Diarylation of Terminal 1,3-Dienes publication-title: ORGANIC LETTERS doi: 10.1021/ol502279u – volume: 344 start-page: 253 year: 1988 ident: WOS:A1988M967300013 article-title: CONDENSATION OF ORGANIC BROMIDES WITH VINYL COMPOUNDS CATALYZED BY NICKEL-COMPLEXES IN THE PRESENCE OF ZINC publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY – volume: 55 start-page: 5757 year: 1990 ident: WOS:A1990EF32200020 article-title: CHELATION-CONTROLLED, PALLADIUM-CATALYZED VINYLIC SUBSTITUTION-REACTIONS OF VINYL ETHERS - 2-ARYLETHANAL EQUIVALENTS FROM ARYL HALIDES publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 13 start-page: 2114 year: 2011 ident: WOS:000289187200057 article-title: Vicinal C-Functionalization of Alkenes. Pd/Light-Induced Multicomponent Coupling Reactions Leading to Functionalized Esters and Lactones publication-title: ORGANIC LETTERS doi: 10.1021/ol200536h – volume: 2015 start-page: 1781 year: 2015 ident: WOS:000351054500017 article-title: Iron-Catalyzed Tandem Cyclization and Cross-Coupling Reactions of Iodoalkanes and Aryl Grignard Reagents publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201403511 – volume: 138 start-page: 14222 year: 2016 ident: WOS:000387095000015 article-title: Copper-Catalyzed Cross-Coupling of Silicon Pronucleophiles with Unactivated Alkyl Electrophiles Coupled with Radical Cyclization publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.6b09596 – volume: 126 start-page: 10250 year: 2004 ident: WOS:000223433700029 article-title: Palladium-catalyzed cyclization/carboalkoxylation of alkenyl indoles publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja046810i – volume: 136 start-page: 3788 year: 2014 ident: WOS:000332922600020 article-title: Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja500706v – volume: 352 start-page: 801 year: 2016 ident: 000407540200016.39 publication-title: Science |
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| Snippet | We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp3)–NiX intermediates with arylzinc reagents.... We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp(3))-NiX intermediates with arylzinc reagents.... We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp )-NiX intermediates with arylzinc reagents.... We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp3)-NiX intermediates with arylzinc reagents.... We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp³)–NiX intermediates with arylzinc reagents.... We disclose a strategy for Ni-catalyzed regioselective dicarbofunctionalization of olefins in styrene derivatives by intercepting Heck C(sp3)-NiX intermediates... |
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| SubjectTerms | alkenes Chemistry Chemistry, Multidisciplinary imines INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY organic halogen compounds Physical Sciences regioselectivity Science & Technology |
| Title | Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles |
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