Nickel-Catalyzed Cross-Electrophile Reductive Couplings of Neopentyl Bromides with Aryl Bromides
5-Cyanoimidazole was identified as an inexpensive ligand for nickel-catalyzed cross-electrophile couplings by screening a diverse set of pharmaceutical compound library. A strategic screening approach led to the discovery of this novel ligand, which was successfully applied in the preparation of var...
Saved in:
| Published in | Journal of organic chemistry Vol. 85; no. 12; pp. 8214 - 8220 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
Amer Chemical Soc
19.06.2020
|
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | 5-Cyanoimidazole was identified as an inexpensive ligand for nickel-catalyzed cross-electrophile couplings by screening a diverse set of pharmaceutical compound library. A strategic screening approach led to the discovery of this novel ligand, which was successfully applied in the preparation of various alkylated arene products with good to high yields. Furthermore, the properties of this ligand allowed expanding the scope of reductive couplings to challenging substrates, such as sterically hindered neopentyl halides, which are known to generate motifs that are prevalent in biologically active molecules. |
|---|---|
| AbstractList | 5-Cyanoimidazole was identified as an inexpensive ligand for nickel-catalyzed cross-electrophile couplings by screening a diverse set of pharmaceutical compound library. A strategic screening approach led to the discovery of this novel ligand, which was successfully applied in the preparation of various alkylated arene products with good to high yields. Furthermore, the properties of this ligand allowed expanding the scope of reductive couplings to challenging substrates, such as sterically hindered neopentyl halides, which are known to generate motifs that are prevalent in biologically active molecules. |
| Author | Song, Jinghua J. Senanayake, Chris H. Choi, Younggi Qu, Bo Desrosiers, Jean-Nicolas Biswas, Soumik Haddad, Nizar Yee, Nathan K. |
| Author_xml | – sequence: 1 givenname: Soumik surname: Biswas fullname: Biswas, Soumik organization: Boehringer Ingelheim Pharmaceut Inc, Chem Dev, 90 E Ridge POB 368, Ridgefield, CT 06877 USA – sequence: 2 givenname: Bo orcidid: 0000-0001-7347-0108 surname: Qu fullname: Qu, Bo email: bo.qu@boehringer-ingelheim.com organization: Boehringer Ingelheim Pharmaceut Inc, Chem Dev, 90 E Ridge POB 368, Ridgefield, CT 06877 USA – sequence: 3 givenname: Jean-Nicolas surname: Desrosiers fullname: Desrosiers, Jean-Nicolas email: nick.desrosiers@pfizer.com organization: Boehringer Ingelheim Pharmaceut Inc, Chem Dev, 90 E Ridge POB 368, Ridgefield, CT 06877 USA – sequence: 4 givenname: Younggi surname: Choi fullname: Choi, Younggi organization: Boehringer Ingelheim Pharmaceut Inc, Chem Dev, 90 E Ridge POB 368, Ridgefield, CT 06877 USA – sequence: 5 givenname: Nizar surname: Haddad fullname: Haddad, Nizar organization: Boehringer Ingelheim Pharmaceut Inc, Chem Dev, 90 E Ridge POB 368, Ridgefield, CT 06877 USA – sequence: 6 givenname: Nathan K. surname: Yee fullname: Yee, Nathan K. organization: Boehringer Ingelheim Pharmaceut Inc, Chem Dev, 90 E Ridge POB 368, Ridgefield, CT 06877 USA – sequence: 7 givenname: Jinghua J. surname: Song fullname: Song, Jinghua J. organization: Boehringer Ingelheim Pharmaceut Inc, Chem Dev, 90 E Ridge POB 368, Ridgefield, CT 06877 USA – sequence: 8 givenname: Chris H. surname: Senanayake fullname: Senanayake, Chris H. organization: Boehringer Ingelheim Pharmaceut Inc, Chem Dev, 90 E Ridge POB 368, Ridgefield, CT 06877 USA |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32452201$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNkUtLxDAQgIMouj7O3qRHQbrmne1Ry_oAURDvNZtONZptapMq6683667i0bkMDN8MM9_sos3Wt4DQIcFjgik51SaMX7wZY4Ox4MUGGhFBcS4LzDfRCGNKc0Yl20G7IbzgFEKIbbTDKBeUYjJCj7fWvILLSx21W3xCnZW9DyGfOjCx992zdZDdQz2YaN8hK_3QOds-hcw32S34Dtq4cNl57-e2hpB92PicnfV_Svtoq9EuwME676GHi-lDeZXf3F1el2c3uaGFinmhKRZKzGosFS4AmK7rRrIJYZoo1WjFpJ7xJi1dgFGNoUQSXXAtyaTWCtgeOl6N7Xr_NkCI1dwGA87pFvwQKsqxLLiQVCX0dIWa5aU9NFXX27nuFxXB1dJqlaxWyWq1tpo6jtbDh9kc6l_-R2MCTlbAB8x8E4yF1sAvttTOmZSKfz8g0ZP_06WNOlrfJvNtZF_G_5ex |
| CitedBy_id | crossref_primary_10_1021_jacs_1c05281 crossref_primary_10_1039_D1NJ01732B crossref_primary_10_1002_adsc_202300188 crossref_primary_10_1016_j_chempr_2023_11_008 crossref_primary_10_1039_D2RA00010E crossref_primary_10_1021_acs_orglett_2c03346 crossref_primary_10_1039_D3CC03058J crossref_primary_10_1002_ejoc_202101440 crossref_primary_10_1021_acs_oprd_0c00367 crossref_primary_10_2174_1570179418666210224124931 crossref_primary_10_1002_chem_202102347 crossref_primary_10_1002_anie_202212421 crossref_primary_10_1002_ange_202212421 crossref_primary_10_1038_s41570_021_00288_z crossref_primary_10_1039_D1CC02885E crossref_primary_10_1021_jacs_3c09554 crossref_primary_10_1021_jacs_3c14607 |
| Cites_doi | 10.1021/jo500905m 10.1021/jacs.5b06255 10.1021/cr100327p 10.1021/jo500507s 10.1021/ja301769r 10.1038/NCHEM.2587 10.1021/acs.accounts.5b00057 10.1021/jacs.7b13601 10.1021/acs.joc.6b02830 10.1016/j.tet.2013.09.039 10.1002/chem.201000178 10.1055/s-0036-1591853 10.1021/ol200617f 10.1021/ja402922w 10.1021/jo049647i 10.1021/acs.organomet.8b00720 10.1002/chem.201402302 10.1021/jacs.6b08856 10.1002/chem.201402509 10.1021/acs.joc.7b01334 10.1021/ol3013342 10.1039/c5qo00224a 10.1021/jacs.6b09533 10.1021/ja9093956 10.1021/jacs.6b04818 10.1038/s41570-017-0052 10.1002/cctc.201900393 10.1021/jm901241e 10.1039/C5QO00224A 10.1038/nchem.2587 |
| ContentType | Journal Article |
| DBID | 1KM 1KN AOWDO BLEPL DTL NPM AAYXX CITATION 7X8 |
| DOI | 10.1021/acs.joc.0c00549 |
| DatabaseName | Index Chemicus Current Chemical Reactions Web of Science - Science Citation Index Expanded - 2020 Web of Science Core Collection Science Citation Index Expanded PubMed CrossRef MEDLINE - Academic |
| DatabaseTitle | Web of Science PubMed CrossRef MEDLINE - Academic |
| DatabaseTitleList | PubMed Web of Science |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1520-6904 |
| EndPage | 8220 |
| ExternalDocumentID | 10_1021_acs_joc_0c00549 32452201 000543667400055 |
| Genre | Journal Article |
| GroupedDBID | --- -DZ -~X .K2 1KM 1KN 29L 4.4 53G 55A 5RE 5VS 7~N 85S AABXI AAHBH ABJNI ABMVS ABPPZ ABQRX ABUCX ACBEA ACGFO ACGFS ACJ ACNCT ACS ADHLV AEESW AENEX AFEFF AGXLV AHGAQ ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH BLEPL CS3 CUPRZ D0L DTL DU5 EBS ED~ F5P GGK GNL GROUPED_WOS_WEB_OF_SCIENCE IH2 IH9 IHE JG~ LG6 P2P PZZ ROL RXW TAE TAF TN5 UI2 UKR UPT VF5 VG9 VQA W1F WH7 XSW YQT YZZ ZCA NPM AAYXX CITATION 7X8 |
| ID | FETCH-LOGICAL-c297t-9a20575bd06709ee3addf63813a177fa736ab4f2209ec7fc2161a94a618da7e3 |
| IEDL.DBID | ACS |
| ISICitedReferencesCount | 15 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000543667400055 |
| ISSN | 0022-3263 |
| IngestDate | Sat Aug 17 03:23:41 EDT 2024 Fri Aug 23 03:09:41 EDT 2024 Sat Sep 28 08:35:48 EDT 2024 Fri Oct 04 21:07:05 EDT 2024 Wed Sep 18 05:34:27 EDT 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 12 |
| Keywords | ALKYL-HALIDES |
| Language | English |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-c297t-9a20575bd06709ee3addf63813a177fa736ab4f2209ec7fc2161a94a618da7e3 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0001-7347-0108 |
| PMID | 32452201 |
| PQID | 2406945627 |
| PQPubID | 23479 |
| PageCount | 7 |
| ParticipantIDs | proquest_miscellaneous_2406945627 crossref_primary_10_1021_acs_joc_0c00549 webofscience_primary_000543667400055 pubmed_primary_32452201 webofscience_primary_000543667400055CitationCount |
| PublicationCentury | 2000 |
| PublicationDate | 2020-06-19 20200619 |
| PublicationDateYYYYMMDD | 2020-06-19 |
| PublicationDate_xml | – month: 06 year: 2020 text: 2020-06-19 day: 19 |
| PublicationDecade | 2020 |
| PublicationPlace | WASHINGTON |
| PublicationPlace_xml | – name: WASHINGTON – name: United States |
| PublicationTitle | Journal of organic chemistry |
| PublicationTitleAbbrev | J ORG CHEM |
| PublicationTitleAlternate | J Org Chem |
| PublicationYear | 2020 |
| Publisher | Amer Chemical Soc |
| Publisher_xml | – name: Amer Chemical Soc |
| References | Guo, WJ (WOS:000326768800008) 2013; 69 Weix, DJ (WOS:000356754600023) 2015; 48 Everson, DA (WOS:000302524800024) 2012; 134 (000543667400055.3) 2001 Corley, EG (WOS:000222760600038) 2004; 69 Chan, VS (WOS:000501378500011) 2019; 11 Molander, GA (WOS:000337871100039) 2014; 79 (000543667400055.4) 2012 Hansen, EC (WOS:000406355900001) 2017; 82 Lovering, F (WOS:000271427900027) 2009; 52 Yu, XL (WOS:000289187200063) 2011; 13 Olivares, AM (WOS:000426143800014) 2018; 140 Jana, R (WOS:000288820600007) 2011; 111 (000543667400055.5) 1998 Wang, SL (WOS:000306050300030) 2012; 14 Wang, X (WOS:000361502800006) 2015; 137 Yan, M (WOS:000384952100001) 2016; 138 Gu, J (WOS:000364450000018) 2015; 2 (000543667400055.2) 2002 Cherney, AH (WOS:000319551000014) 2013; 135 Richmond, E (WOS:000422936300006) 2018; 50 Zhang, XH (WOS:000386540500025) 2016; 138 Zhang, P (WOS:000379455600011) 2016; 138 Campeau, LC (WOS:000456349500002) 2019; 38 Paul, A (WOS:000394736000016) 2017; 82 Everson, DA (WOS:000275084700009) 2010; 132 Amatore, M (WOS:000278596600004) 2010; 16 Everson, DA (WOS:000337073900002) 2014; 79 Hansen, EC (WOS:000389225700010) 2016; 8 (000543667400055.1) 2005 Knappke, CEI (WOS:000337574800001) 2014; 20 Moragas, T (WOS:000338019300001) 2014; 20 Twilton, J (WOS:000415236400002) 2017; 1 ref9/cit9 ref6/cit6 ref3/cit3 ref1/cit1e ref18/cit18 ref1/cit1d ref1/cit1g ref1/cit1f ref16/cit16 ref10/cit10a ref10/cit10b ref14/cit14 ref2/cit2c ref8/cit8 ref2/cit2b ref2/cit2a ref1/cit1a ref1/cit1c ref1/cit1b ref5/cit5b ref17/cit17 ref5/cit5c ref5/cit5a ref19/cit19 ref12/cit12 ref11/cit11c ref11/cit11b ref11/cit11e ref11/cit11d ref11/cit11a ref4/cit4 ref5/cit5d ref7/cit7 |
| References_xml | – volume: 79 start-page: 5771 year: 2014 ident: WOS:000337871100039 article-title: Reductive Cross-Coupling of Nonaromatic, Heterocyclic Bromides with Aryl and Heteroaryl Bromides publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo500905m contributor: fullname: Molander, GA – year: 1998 ident: 000543667400055.5 article-title: Preparation of Carbazole Derivatives as Selective 3 Adrenergic Agonists publication-title: PCT Int. Appl. – volume: 137 start-page: 11562 year: 2015 ident: WOS:000361502800006 article-title: Nickel-Catalyzed Reductive Coupling of Aryl Bromides with Tertiary Alkyl Halides publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.5b06255 contributor: fullname: Wang, X – volume: 111 start-page: 1417 year: 2011 ident: WOS:000288820600007 article-title: Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners publication-title: CHEMICAL REVIEWS doi: 10.1021/cr100327p contributor: fullname: Jana, R – volume: 79 start-page: 4793 year: 2014 ident: WOS:000337073900002 article-title: Cross-Electrophile Coupling: Principles of Reactivity and Selectivity publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo500507s contributor: fullname: Everson, DA – year: 2001 ident: 000543667400055.3 article-title: Preparation of Nitrogencontaining Heterocyclic Compounds as Medical and Agrochemical Fungicides publication-title: PCT Int. Appl. – volume: 134 start-page: 6146 year: 2012 ident: WOS:000302524800024 article-title: Replacing Conventional Carbon Nucleophiles with Electrophiles: Nickel-Catalyzed Reductive Alkylation of Aryl Bromides and Chlorides publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja301769r contributor: fullname: Everson, DA – volume: 8 start-page: 1126 year: 2016 ident: WOS:000389225700010 article-title: New ligands for nickel catalysis from diverse pharmaceutical heterocycle libraries publication-title: NATURE CHEMISTRY doi: 10.1038/NCHEM.2587 contributor: fullname: Hansen, EC – volume: 48 start-page: 1767 year: 2015 ident: WOS:000356754600023 article-title: Methods and Mechanisms for Cross-Electrophile Coupling of Csp(2) Halides with Alkyl Electrophiles publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/acs.accounts.5b00057 contributor: fullname: Weix, DJ – year: 2012 ident: 000543667400055.4 article-title: Method for Producing Hematopoietic Stem Cells Using Pyrazole Compound publication-title: PCT Int. Appl. – volume: 140 start-page: 2446 year: 2018 ident: WOS:000426143800014 article-title: Multimetallic Ni- and Pd-Catalyzed Cross-Electrophile Coupling To Form Highly Substituted 1,3-Dienes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b13601 contributor: fullname: Olivares, AM – year: 2002 ident: 000543667400055.2 article-title: Preparation of Naphthalenylethylaminopropanol Derivatives as Calcium Receptor Antagonists publication-title: PCT Int. Appl. – volume: 82 start-page: 1996 year: 2017 ident: WOS:000394736000016 article-title: Photoredox-Assisted Reductive Cross-Coupling: Mechanistic Insight into Catalytic Aryl-Alkyl Cross-Couplings publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.6b02830 contributor: fullname: Paul, A – volume: 69 start-page: 9580 year: 2013 ident: WOS:000326768800008 article-title: Iron-catalyzed cross-coupling of aryltrimethylammonium triflates and alkyl Grignard reagents publication-title: TETRAHEDRON doi: 10.1016/j.tet.2013.09.039 contributor: fullname: Guo, WJ – year: 2005 ident: 000543667400055.1 article-title: Preparation of Fused Heterotetracyclic Compounds and Use Thereof as Hepatitis C Virus (HCV) Polymerase Inhibitors publication-title: PCT Int. Appl – volume: 16 start-page: 5848 year: 2010 ident: WOS:000278596600004 article-title: Direct Method for Carbon-Carbon Bond Formation: The Functional Group Tolerant Cobalt-Catalyzed Alkylation of Aryl Halides publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201000178 contributor: fullname: Amatore, M – volume: 50 start-page: 499 year: 2018 ident: WOS:000422936300006 article-title: Recent Advances in Nickel Catalysis Enabled by Stoichiometric Metallic Reducing Agents publication-title: SYNTHESIS-STUTTGART doi: 10.1055/s-0036-1591853 contributor: fullname: Richmond, E – volume: 13 start-page: 2138 year: 2011 ident: WOS:000289187200063 article-title: Nickel-Catalyzed Reductive Cross-Coupling of Unactivated Alkyl Halides publication-title: ORGANIC LETTERS doi: 10.1021/ol200617f contributor: fullname: Yu, XL – volume: 135 start-page: 7442 year: 2013 ident: WOS:000319551000014 article-title: Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic alpha,alpha-Disubstituted Ketones publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja402922w contributor: fullname: Cherney, AH – volume: 69 start-page: 5120 year: 2004 ident: WOS:000222760600038 article-title: Direct synthesis of 4-arylpiperidines via palladium/copper(I)-cocatalyzed Negishi coupling of a 4-piperidylzinc iodide with aromatic halides and triflates publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo049647i contributor: fullname: Corley, EG – volume: 38 start-page: 3 year: 2019 ident: WOS:000456349500002 article-title: Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future publication-title: ORGANOMETALLICS doi: 10.1021/acs.organomet.8b00720 contributor: fullname: Campeau, LC – volume: 20 start-page: 6828 year: 2014 ident: WOS:000337574800001 article-title: Reductive Cross-Coupling Reactions between Two Electrophiles publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201402302 contributor: fullname: Knappke, CEI – volume: 138 start-page: 12692 year: 2016 ident: WOS:000384952100001 article-title: Radicals: Reactive Intermediates with Translational Potential publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.6b08856 contributor: fullname: Yan, M – volume: 20 start-page: 8242 year: 2014 ident: WOS:000338019300001 article-title: Metal-Catalyzed Reductive Coupling Reactions of Organic Halides with Carbonyl-Type Compounds publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201402509 contributor: fullname: Moragas, T – volume: 82 start-page: 7085 year: 2017 ident: WOS:000406355900001 article-title: Coupling of Challenging Heteroaryl Halides with Alkyl Halides via Nickel-Catalyzed Cross-Electrophile Coupling publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.7b01334 contributor: fullname: Hansen, EC – volume: 14 start-page: 3352 year: 2012 ident: WOS:000306050300030 article-title: Nickel-Catalyzed Reductive Coupling of Aryl Halides with Secondary Alkyl Bromides and Allylic Acetate publication-title: ORGANIC LETTERS doi: 10.1021/ol3013342 contributor: fullname: Wang, SL – volume: 2 start-page: 1411 year: 2015 ident: WOS:000364450000018 article-title: Nickel-catalyzed reductive coupling of alkyl halides with other electrophiles: concept and mechanistic considerations publication-title: ORGANIC CHEMISTRY FRONTIERS doi: 10.1039/c5qo00224a contributor: fullname: Gu, J – volume: 138 start-page: 13862 year: 2016 ident: WOS:000386540500025 article-title: Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: sp(3)-sp(2) Cross-Coupling of Oxalates with Aryl Halides publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.6b09533 contributor: fullname: Zhang, XH – volume: 132 start-page: 920 year: 2010 ident: WOS:000275084700009 article-title: Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja9093956 contributor: fullname: Everson, DA – volume: 138 start-page: 8084 year: 2016 ident: WOS:000379455600011 article-title: Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.6b04818 contributor: fullname: Zhang, P – volume: 1 start-page: ARTN 0052 year: 2017 ident: WOS:000415236400002 article-title: The merger of transition metal and photocatalysis publication-title: NATURE REVIEWS CHEMISTRY doi: 10.1038/s41570-017-0052 contributor: fullname: Twilton, J – volume: 11 start-page: 5748 year: 2019 ident: WOS:000501378500011 article-title: Identification of an Oxalamide Ligand for Copper-Catalyzed C-O Couplings from a Pharmaceutical Compound Library publication-title: CHEMCATCHEM doi: 10.1002/cctc.201900393 contributor: fullname: Chan, VS – volume: 52 start-page: 6752 year: 2009 ident: WOS:000271427900027 article-title: Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm901241e contributor: fullname: Lovering, F – ident: ref7/cit7 doi: 10.1021/ol200617f – ident: ref2/cit2b doi: 10.1021/jacs.6b08856 – ident: ref10/cit10b doi: 10.1021/jacs.6b04818 – ident: ref11/cit11d – ident: ref4/cit4 doi: 10.1021/jacs.5b06255 – ident: ref9/cit9 doi: 10.1021/acs.joc.7b01334 – ident: ref17/cit17 doi: 10.1016/j.tet.2013.09.039 – ident: ref2/cit2a doi: 10.1021/cr100327p – ident: ref11/cit11b – ident: ref18/cit18 doi: 10.1021/jacs.6b09533 – ident: ref1/cit1e doi: 10.1039/C5QO00224A – ident: ref1/cit1d doi: 10.1021/acs.accounts.5b00057 – ident: ref19/cit19 doi: 10.1021/jo049647i – ident: ref1/cit1f doi: 10.1055/s-0036-1591853 – ident: ref16/cit16 doi: 10.1002/chem.201000178 – ident: ref1/cit1b doi: 10.1002/chem.201402509 – ident: ref5/cit5c doi: 10.1021/ol3013342 – ident: ref12/cit12 doi: 10.1002/cctc.201900393 – ident: ref14/cit14 doi: 10.1021/jo500905m – ident: ref8/cit8 doi: 10.1038/nchem.2587 – ident: ref10/cit10a doi: 10.1021/acs.joc.6b02830 – ident: ref11/cit11e – ident: ref1/cit1a doi: 10.1021/jo500507s – ident: ref1/cit1c doi: 10.1002/chem.201402302 – ident: ref11/cit11c – ident: ref1/cit1g doi: 10.1021/acs.organomet.8b00720 – ident: ref11/cit11a – ident: ref3/cit3 doi: 10.1021/jm901241e – ident: ref5/cit5d doi: 10.1021/jacs.7b13601 – ident: ref5/cit5a doi: 10.1021/ja9093956 – ident: ref5/cit5b doi: 10.1021/ja301769r – ident: ref2/cit2c doi: 10.1038/s41570-017-0052 – ident: ref6/cit6 doi: 10.1021/ja402922w |
| SSID | ssj0000555 |
| Score | 2.4584503 |
| Snippet | 5-Cyanoimidazole was identified as an inexpensive ligand for nickel-catalyzed cross-electrophile couplings by screening a diverse set of pharmaceutical... |
| Source | Web of Science |
| SourceID | proquest crossref pubmed webofscience |
| SourceType | Aggregation Database Index Database Enrichment Source |
| StartPage | 8214 |
| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Nickel-Catalyzed Cross-Electrophile Reductive Couplings of Neopentyl Bromides with Aryl Bromides |
| URI | http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000543667400055 https://www.ncbi.nlm.nih.gov/pubmed/32452201 https://search.proquest.com/docview/2406945627 |
| Volume | 85 |
| WOS | 000543667400055 |
| WOSCitedRecordID | wos000543667400055 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV07T8MwELZQF1h4P8JLRurAktI4iY1HFLWqkOgAReoWHMfh0ZJUJBnaX48vSdNCkeiat-8ud599vu8QalKLCqpo2-QkDEwnsgJTCAfW4COiuGyzSEGB80Of9p6d-6E7XJBF_87gE-tGyLT1kchWWwK8KEr1dFQDEOQ9LXyu67o1Lzihdk3is3L_z_izAir_jD9FrOnulLu00oKiELaYjFp5FrTkbJXA8f9h7KLtCnHiu9JE9tCGivfRpjdv9HaAXrQ1jNTY9GAlZzpTIfbg081O2SFn8qYdB34EildwjdhLcqjifU1xEuG-gvZb2XSM9Xz-8z1UKYaVXf22pUOHaNDtDLyeWTVeMCXhLDO5IADjghCKeLhStnaCkf5RLVtYjEWC2VQEWplEn5QskkTDRsEdQa3bUDBlH6FGnMTqBGHgTA8lD2RIpSOJ4JQRqsDPuFEomW2g67k2_ElJr-EXaXFi-VpivpaYX0nMQFdzbflaQJDXELFK8tQvq3c1kGMGOi7VWD_MhsyyBjkGai7rtT5fYFabUuYURmQga53LvIo_HXgDstP1x3CGtgjM16H3ET9HjewrVxca1GTBZWHP343y8tc |
| link.rule.ids | 315,786,790,2782,27957,27958 |
| linkProvider | American Chemical Society |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Nickel-Catalyzed+Cross-Electrophile+Reductive+Couplings+of+Neopentyl+Bromides+with+Aryl+Bromides&rft.jtitle=Journal+of+organic+chemistry&rft.au=Biswas%2C+Soumik&rft.au=Qu%2C+Bo&rft.au=Desrosiers%2C+Jean-Nicolas&rft.au=Choi%2C+Younggi&rft.date=2020-06-19&rft.eissn=1520-6904&rft.volume=85&rft.issue=12&rft.spage=8214&rft_id=info:doi/10.1021%2Facs.joc.0c00549&rft_id=info%3Apmid%2F32452201&rft.externalDocID=32452201 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0022-3263&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0022-3263&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0022-3263&client=summon |