Nickel(0)-Catalyzed Formation of Oxaaluminacyclopentenes via an Oxanickelacyclopentene Key Intermediate: Me2AlOTf-Assisted Oxidative Cyclization of an Aldehyde and an Alkyne with Nickel(0)
The use of Me2AlOTf as an additive allowed the oxidative cyclization of pivalaldehyde and diphenylacetylene with nickel(0) in the presence of PCy3 to give an oxanickelacyclopentene, the structure of which was unambiguously determined by means of X-ray diffraction study. In the presence of TMSCHCH2,...
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Published in | Organometallics Vol. 29; no. 23; pp. 6534 - 6540 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
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Abstract | The use of Me2AlOTf as an additive allowed the oxidative cyclization of pivalaldehyde and diphenylacetylene with nickel(0) in the presence of PCy3 to give an oxanickelacyclopentene, the structure of which was unambiguously determined by means of X-ray diffraction study. In the presence of TMSCHCH2, treatment of the oxanickelacyclopentene with an equimolar amount of AlMe3 quantitatively gave an oxaaluminacyclopentene with simultaneous generation of ethane and the Ni(0) species (PCy3)Ni(TMSCHCH2)2. The oxaaluminacyclopentene was a suitable precursor for the preparation of allylic alcohol derivatives due to its reactive Al−C bond, and treatment with HCl or I2 afforded (E)-4,4-dimethyl-1,2-diphenylpent-1-en-3-ol and (E)-PhCHC(Ph)CH( t Bu)OH, and (Z)-1-iodo-4,4-dimethyl-1,2-diphenylpent-1-en-3-ol and (Z)-PhCIC(Ph)CH( t Bu)OH, respectively, in excellent yield. This sequential reaction was successfully expanded to a Ni(0)-catalyzed three-component cyclocondensation reaction of an aldehyde, an alkyne, and AlMe3 that gave the corresponding oxaaluminacyclopentenes in moderate to good yields. The scope of substrates and the mechanism of the reaction are also reported. |
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AbstractList | The use of Me2AlOTf as an additive allowed the oxidative cyclization of pivalaldehyde and diphenylacetylene with nickel(0) in the presence of PCy3 to give an oxanickelacyclopentene, the structure of which was unambiguously determined by means of X-ray diffraction study. In the presence of TMSCH=CH2, treatment of the oxanickelacyclopentene with an equimolar amount of AlMe3 quantitatively gave an oxaaluminacyclopentene with simultaneous generation of ethane and the Ni(0) species (PCy3)Ni-(TMSCH=CH2)(2). The oxaaluminacyclopentene was a suitable precursor for the preparation of allylic alcohol derivatives due to its reactive Al-C bond, and treatment with HCl or I-2 afforded (E)-4,4-dimethyl-1,2-diphenylpent- 1 -en-3-ol and (E)-PhCH=C(Ph)CH('Bu)OH, and (Z)-I-iodo-4,4-dimethy1-1,2-diphenylpent-1-en-3-ol and (Z)-PhCI=C(Ph)CH('Bu)OH, respectively, in excellent yield. This sequential reaction was successfully expanded to a Ni(0)-catalyzed three-component cyclocondensation reaction of an aldehyde, an alkyne, and AlMe3 that gave the corresponding oxaaluminacyclopentenes in moderate to good yields. The scope of substrates and the mechanism of the reaction are also reported. The use of Me2AlOTf as an additive allowed the oxidative cyclization of pivalaldehyde and diphenylacetylene with nickel(0) in the presence of PCy3 to give an oxanickelacyclopentene, the structure of which was unambiguously determined by means of X-ray diffraction study. In the presence of TMSCHCH2, treatment of the oxanickelacyclopentene with an equimolar amount of AlMe3 quantitatively gave an oxaaluminacyclopentene with simultaneous generation of ethane and the Ni(0) species (PCy3)Ni(TMSCHCH2)2. The oxaaluminacyclopentene was a suitable precursor for the preparation of allylic alcohol derivatives due to its reactive Al−C bond, and treatment with HCl or I2 afforded (E)-4,4-dimethyl-1,2-diphenylpent-1-en-3-ol and (E)-PhCHC(Ph)CH( t Bu)OH, and (Z)-1-iodo-4,4-dimethyl-1,2-diphenylpent-1-en-3-ol and (Z)-PhCIC(Ph)CH( t Bu)OH, respectively, in excellent yield. This sequential reaction was successfully expanded to a Ni(0)-catalyzed three-component cyclocondensation reaction of an aldehyde, an alkyne, and AlMe3 that gave the corresponding oxaaluminacyclopentenes in moderate to good yields. The scope of substrates and the mechanism of the reaction are also reported. |
Author | Ohashi, Masato Saijo, Hiroki Arai, Tomoya Ogoshi, Sensuke |
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Cites_doi | 10.1021/ja0542486 10.1002/anie.200300634 10.1021/ja072992f 10.1070/RC2000V069N02ABEH000519 10.1021/ja900701g 10.1021/ja0446799 10.1039/b604742d 10.1021/ol052719n 10.1007/128_2007_139 10.1002/anie.200700688 10.1021/ol902561r 10.1021/ja001440t 10.1021/ol801534e 10.1039/b926866a 10.1016/j.tetasy.2003.07.010 10.1016/j.tet.2006.03.122 10.1021/ar990095d 10.1021/ja903510u 10.1021/ol050881k 10.1021/ol0515558 10.1021/ol025812+ 10.1021/ja060220y 10.1039/b717261c 10.1351/pac200678020511 10.1021/ja903175g 10.1021/ja803774s 10.1021/ja060580l 10.1021/ol0272996 10.1021/jo0613535 10.1039/b707737h 10.1021/ja9083607 10.1021/om100317y 10.1007/128_2007_122 10.1021/ar7001123 10.1002/chem.200900929 10.1016/j.jorganchem.2006.08.016 10.1002/anie.200301673 10.1021/ja0552895 10.1021/ja049644n 10.1021/jo702508w 10.1021/ja0491735 10.1055/s-2006-942507 10.1002/anie.200462569 10.1021/ol051075g 10.1246/cl.2009.1166 10.1021/ja909562y 10.1002/anie.200460044 10.1021/ja102262v 10.1351/pac200880051115 10.1021/ja034366y 10.1016/j.jorganchem.2004.04.047 10.1021/ja805296k 10.1021/ol061579u 10.1021/ja0460716 10.1016/j.ica.2007.09.005 10.1007/128_2007_121 10.1021/ja054590i 10.1021/ja0175845 |
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Keywords | TETHERED ALKENES CATALYZED REDUCTIVE COUPLINGS ALLYLIC ALCOHOLS UNSATURATED-HYDROCARBONS C-C NICKELACYCLIC CARBOXYLATES CARBONYL-COMPOUNDS LIGAND TRIALKYLALUMINUM ADDITION ACCESS |
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References | Tekevac, TN (WOS:000231520000054) 2005; 7 WALTHER, D (WOS:A1980JV65000008) 1980; 190 Langer, J (WOS:000223804300002) 2004; 689 Murakami, M (WOS:000235562900006) 2006; 128 Ogoshi, S (WOS:000255841500032) 2008; 80 KAISER, J (WOS:A1982NS19600045) 1982; 38 Biswas, K (WOS:000235784500038) 2006; 78 Moslin, RA (WOS:000239065900014) 2006; 62 Miller, KM (WOS:000220637100040) 2004; 126 WALTHER, D (WOS:A1977DK27800002) 1977; 431 Oblinger, E (WOS:A1997XX82000044) 1997; 119 Tekavec, TN (WOS:000254544800019) 2008; 73 Ohashi, M (WOS:000278427400002) 2010; 29 Kimura, M (WOS:000250385200008) 2007; 279 Moslin, RM (WOS:000235120700026) 2006; 8 Knapp-Reed, B (WOS:000232170800038) 2005; 127 Iida, H (WOS:000250385200005) 2007; 279 TSUDA, T (WOS:A1988R339800057) 1988; 110 DZHEMILEV UM (WOS:000284866000047.8) 2000; 69 Yang, Y (WOS:000260301700016) 2008; 130 Borisenko, KB (WOS:A1996UJ11700018) 1996; 100 Sa-ei, K (WOS:000240654700015) 2006; 8 Langer, J (WOS:000242304900008) 2006; 691 Li, W (WOS:000272185400077) 2009; 131 Miller, KM (WOS:000181755800021) 2003; 125 Luanphaisarnnont, T (WOS:000230213100034) 2005; 7 Ohashi, M (WOS:000267633300014) 2009; 131 Miller, KM (WOS:000186693200026) 2003; 14 WALTHER, D (WOS:A1992JN41600012) 1992; 436 Tamaki, T (WOS:000270854200019) 2009; 15 Mahandru, GM (WOS:000220440400014) 2004; 126 Montgomery, J (WOS:000223047200003) 2004; 43 Mata, Y (WOS:000254858200022) 2008; 361 Takai, K (WOS:000181233000013) 2003; 5 Montgomery, J (WOS:000088521700004) 2000; 33 Chaulagain, MR (WOS:000248484400018) 2007; 129 Montgomery, J (WOS:000250385200002) 2007; 279 Patel, SJ (WOS:000223047200013) 2004; 43 Ogoshi, S (WOS:000237816300053) 2006; 128 Langer, J (WOS:000240187000013) 2006 Ogoshi, S (WOS:000277318000037) 2010; 46 Baxter, RD (WOS:000257902500021) 2008; 130 Biswas, K (WOS:000228415900010) 2005; 44 Tang, XQ (WOS:000088522700017) 2000; 122 Liu, P (WOS:000275085000070) 2010; 132 Mata, Y (WOS:000241053000028) 2006; 71 McCarren, PR (WOS:000266096900006) 2009; 131 Ogoshi, S (WOS:000237125100025) 2006; 128 Moslin, RM (WOS:000250588900001) 2007 Ogoshi, S (WOS:000231928800031) 2005; 127 Ogoshi, S (WOS:000224103900026) 2004; 126 Saito, N (WOS:000258833700045) 2008; 10 Aksin, O (WOS:000239211700009) 2006 Miller, KM (WOS:000225349800012) 2004; 126 Ogoshi, S (WOS:000247773300014) 2007; 46 Lozanov, M (WOS:000174469600017) 2002; 124 Ogoshi, S (WOS:000254352900025) 2008 Tang, XQ (WOS:000081216800042) 1999; 121 Skucas, E (WOS:000251787500019) 2007; 40 Ni, YK (WOS:000175585000028) 2002; 4 Malik, HA (WOS:000272461800042) 2009; 11 DZHEMILEV, UM (WOS:A1994MW51100001) 1994; 466 Miller, KM (WOS:000230213100069) 2005; 7 OGOSHI S (WOS:000284866000047.51) 2010 Ikeda, S (WOS:000186550800001) 2003; 42 Ogoshi, S (WOS:000273859200020) 2009; 38 Huang, WS (WOS:000166017300027) 2000; 2 Malik, HA (WOS:000277445400015) 2010; 132 Ogoshi, S (WOS:000268644400008) 2009; 131 Patel, SJ (WOS:000182095700007) 2003; 42 |
References_xml | – volume: 38 start-page: 1584 year: 1982 ident: WOS:A1982NS19600045 article-title: BENZALDEHYDEBIS(TRICYCLOHEXYLPHOSPHINE)NICKEL(O) publication-title: ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS contributor: fullname: KAISER, J – volume: 190 start-page: 393 year: 1980 ident: WOS:A1980JV65000008 article-title: REACTIONS OF HETEROOLEFINS ON CENTRAL METALS IN LOW OXIDATION STAGES - STABLE ALDEHYDE COMPLEXES OF NICKEL(0) AND RELATED-COMPOUNDS publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: WALTHER, D – volume: 127 start-page: 12810 year: 2005 ident: WOS:000231928800031 article-title: AlMe3-promoted oxidative cyclization of eta(2)-alkene and eta(2)-ketone on nickel(0). Observation of intermediate in methyl transfer process publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0542486 contributor: fullname: Ogoshi, S – volume: 43 start-page: 3890 year: 2004 ident: WOS:000223047200003 article-title: Nickel-catalyzed reductive cyclizations and couplings publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200300634 contributor: fullname: Montgomery, J – volume: 121 start-page: 6098 year: 1999 ident: WOS:000081216800042 article-title: Nickel catalysis in the stereoselective preparation of quinolizidine, pyrrolizidine, and indolizidine alkaloids: Total synthesis of (+)-allopumiliotoxin 267A publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Tang, XQ – volume: 129 start-page: 9568 year: 2007 ident: WOS:000248484400018 article-title: New N-heterocyclic carbene ligand and its application in asymmetric nickel-catalyzed aldehyde/alkyne reductive couplings publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja072992f contributor: fullname: Chaulagain, MR – volume: 69 start-page: 121 year: 2000 ident: WOS:000284866000047.8 publication-title: RUSS CHEM REV doi: 10.1070/RC2000V069N02ABEH000519 contributor: fullname: DZHEMILEV UM – volume: 42 start-page: 1364 year: 2003 ident: WOS:000182095700007 article-title: Catalytic three-component coupling of alkynes, imines, and organoboron reagents publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Patel, SJ – volume: 466 start-page: 1 year: 1994 ident: WOS:A1994MW51100001 article-title: REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS FOR A NOVEL CLASS OF ORGANOALUMINUM COMPOUNDS - SUBSTITUTED ALUMINACYCLOPENTANES AND ALUMINACYCLOPENTENES ASSISTED BY ZIRCONIUM CATALYSTS publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: DZHEMILEV, UM – volume: 131 start-page: 6654 year: 2009 ident: WOS:000266096900006 article-title: Mechanism and Transition-State Structures for Nickel-Catalyzed Reductive Alkyne-Aldehyde Coupling Reactions publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja900701g contributor: fullname: McCarren, PR – volume: 126 start-page: 15342 year: 2004 ident: WOS:000225349800012 article-title: Ligand-switchable directing effects of tethered alkenes in nickel-catalyzed additions to alkynes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0446799 contributor: fullname: Miller, KM – volume: 2 start-page: 4221 year: 2000 ident: WOS:000166017300027 article-title: Highly selective catalytic intermolecular reductive coupling of alkynes and aldehydes publication-title: ORGANIC LETTERS contributor: fullname: Huang, WS – start-page: 3187 year: 2006 ident: WOS:000239211700009 article-title: Rhodium-catalyzed carbonylative arylation of alkynes with arylboronic acids: an efficient and straightforward method in the synthesis of 5-aryl-2(5H)-furanones publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b604742d contributor: fullname: Aksin, O – volume: 8 start-page: 455 year: 2006 ident: WOS:000235120700026 article-title: Mechanistic implications of nickel-catalyzed reductive coupling of aldehydes and chiral 1,6-enynes publication-title: ORGANIC LETTERS doi: 10.1021/ol052719n contributor: fullname: Moslin, RM – volume: 279 start-page: 1 year: 2007 ident: WOS:000250385200002 article-title: Nickel-catalyzed reductive couplings of aldehydes and alkynes publication-title: METAL CATALYZED REDUCTIVE C-C BOND FORMATION: A DEPARTURE FROM PREFORMED ORGANOMETALLIC REAGENTS doi: 10.1007/128_2007_139 contributor: fullname: Montgomery, J – volume: 46 start-page: 4930 year: 2007 ident: WOS:000247773300014 article-title: Formation of an aza-nickelacycle by reaction of an imine and an alkyne with nickel(0): Oxidative cyclization, insertion, and reductive elimination publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200700688 contributor: fullname: Ogoshi, S – volume: 11 start-page: 5734 year: 2009 ident: WOS:000272461800042 article-title: Cooperativity of Regiochemistry Control Strategies in Reductive Couplings of Propargyl Alcohols and Aldehydes publication-title: ORGANIC LETTERS doi: 10.1021/ol902561r contributor: fullname: Malik, HA – volume: 122 start-page: 6950 year: 2000 ident: WOS:000088522700017 article-title: Nickel-catalyzed preparation of bicyclic heterocycles: Total synthesis of (+)-allopumiliotoxin 267A, (+)-allopumiliotoxin 339A, and (+)-allopumiliotoxin 339B publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja001440t contributor: fullname: Tang, XQ – volume: 10 start-page: 3829 year: 2008 ident: WOS:000258833700045 article-title: Nickel-catalyzed highly regioselective multicomponent coupling of ynamides, aldehydes, and silane: A new access to functionalized enamides publication-title: ORGANIC LETTERS doi: 10.1021/ol801534e contributor: fullname: Saito, N – volume: 46 start-page: 3354 year: 2010 ident: WOS:000277318000037 article-title: Nickel-catalyzed Tishchenko reaction via hetero-nickelacycles by oxidative cyclization of aldehydes with nickel(0) complex publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b926866a contributor: fullname: Ogoshi, S – volume: 14 start-page: 3619 year: 2003 ident: WOS:000186693200026 article-title: Catalytic reductive carbon-carbon bond-forming reactions of alkynes publication-title: TETRAHEDRON-ASYMMETRY doi: 10.1016/j.tetasy.2003.07.010 contributor: fullname: Miller, KM – volume: 62 start-page: 7598 year: 2006 ident: WOS:000239065900014 article-title: Directing effects of tethered alkenes in nickel-catalyzed coupling reactions of 1,6-enynes and aldehydes publication-title: TETRAHEDRON doi: 10.1016/j.tet.2006.03.122 contributor: fullname: Moslin, RA – volume: 33 start-page: 467 year: 2000 ident: WOS:000088521700004 article-title: Nickel-catalyzed cyclizations, couplings, and cycloadditions involving three reactive components publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar990095d contributor: fullname: Montgomery, J – volume: 131 start-page: 10350 year: 2009 ident: WOS:000268644400008 article-title: Nickel-Catalyzed Direct Conjugate Addition of Simple Alkenes to Enones publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja903510u contributor: fullname: Ogoshi, S – volume: 7 start-page: 2937 year: 2005 ident: WOS:000230213100034 article-title: anti-1,2-diols via Ni-catalyzed reductive coupling of alkynes and alpha-oxyaldehydes publication-title: ORGANIC LETTERS doi: 10.1021/ol050881k contributor: fullname: Luanphaisarnnont, T – volume: 7 start-page: 4037 year: 2005 ident: WOS:000231520000054 article-title: Nickel-catalyzed cycloaddition of unsaturated hydrocarbons and carbonyl compounds publication-title: ORGANIC LETTERS doi: 10.1021/ol0515558 contributor: fullname: Tekevac, TN – volume: 4 start-page: 1743 year: 2002 ident: WOS:000175585000028 article-title: Nickel-catalyzed cyclizations and couplings with vinylzirconium reagents publication-title: ORGANIC LETTERS doi: 10.1021/ol025812+ contributor: fullname: Ni, YK – volume: 128 start-page: 5350 year: 2006 ident: WOS:000237125100025 article-title: Formation of nickeladihydropyran by oxidative addition of cyclopropyl ketone. Key intermediate in nickel-catalyzed cycloaddition publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja060220y contributor: fullname: Ogoshi, S – start-page: 1347 year: 2008 ident: WOS:000254352900025 article-title: Nickeladihydrofuran. Key intermediate for nickel-catalyzed reaction of alkyne and aldehyde publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b717261c contributor: fullname: Ogoshi, S – volume: 78 start-page: 511 year: 2006 ident: WOS:000235784500038 article-title: Dabbling with air-stable organoaluminum species publication-title: PURE AND APPLIED CHEMISTRY doi: 10.1351/pac200678020511 contributor: fullname: Biswas, K – volume: 131 start-page: 9160 year: 2009 ident: WOS:000267633300014 article-title: Ni(O)-Catalyzed Formation of Azaaluminacyclopentenes via Azanickelacyclopentenes: A Unique Nickel/Aluminum Double Transmetalation Reaction publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja903175g contributor: fullname: Ohashi, M – volume: 130 start-page: 9662 year: 2008 ident: WOS:000257902500021 article-title: Dehydrogenative cyclocondensation of aldehydes, alkynes, and dialkylsilanes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja803774s contributor: fullname: Baxter, RD – volume: 128 start-page: 7077 year: 2006 ident: WOS:000237816300053 article-title: Reversible carbon-carbon bond formation between 1,3-dienes and aldehyde or ketone on nickel(0) publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja060580l contributor: fullname: Ogoshi, S – volume: 5 start-page: 653 year: 2003 ident: WOS:000181233000013 article-title: Regioselective reductive coupling of alkynes and aldehydes leading to allylic alcohols publication-title: ORGANIC LETTERS doi: 10.1021/ol0272996 contributor: fullname: Takai, K – volume: 71 start-page: 8159 year: 2006 ident: WOS:000241053000028 article-title: Screening of a modular sugar-based phosphite ligand library in the asymmetric nickel-catalyzed trialkylaluminum addition to aldehydes publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo0613535 contributor: fullname: Mata, Y – start-page: 4441 year: 2007 ident: WOS:000250588900001 article-title: Regioselectivity and enantioselectivity in nickel-catalysed reductive coupling reactions of alkynes publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b707737h contributor: fullname: Moslin, RM – volume: 131 start-page: 17024 year: 2009 ident: WOS:000272185400077 article-title: Evolution of Efficient Strategies for Enone-Alkyne and Enal-Alkyne Reductive Couplings publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja9083607 contributor: fullname: Li, W – volume: 29 start-page: 2386 year: 2010 ident: WOS:000278427400002 article-title: [3+3] Cyclodimerization of Methylenecyclopropanes: Stoichiometric and Catalytic Reactions of Nickel(0) with Electron-Deficient Alkylidenecyclopropanes publication-title: ORGANOMETALLICS doi: 10.1021/om100317y contributor: fullname: Ohashi, M – volume: 279 start-page: 77 year: 2007 ident: WOS:000250385200005 article-title: Catalytic reductive coupling of alkenes and alkynes to carbonyl compounds and imines mediated by hydrogen publication-title: METAL CATALYZED REDUCTIVE C-C BOND FORMATION: A DEPARTURE FROM PREFORMED ORGANOMETALLIC REAGENTS doi: 10.1007/128_2007_122 contributor: fullname: Iida, H – volume: 40 start-page: 1394 year: 2007 ident: WOS:000251787500019 article-title: Enantiomerically enriched allylic alcohols and allylic amines via C-C bond-forming hydrogenation: Asymmetric carbonyl and imine vinylation publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar7001123 contributor: fullname: Skucas, E – volume: 15 start-page: 10083 year: 2009 ident: WOS:000270854200019 article-title: Synthesis and Reactivity of Six-Membered Oxa-Nickelacycles: A Ring-Opening Reaction of Cyclopropyl Ketones publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200900929 contributor: fullname: Tamaki, T – volume: 110 start-page: 8570 year: 1988 ident: WOS:A1988R339800057 article-title: NICKEL(0)-CATALYZED REACTION OF DIYNES WITH ALDEHYDES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: TSUDA, T – volume: 691 start-page: 4874 year: 2006 ident: WOS:000242304900008 article-title: Saturated and unsaturated nickelalactones with N-heterocyclic carbene ligands: Synthesis and structures publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY doi: 10.1016/j.jorganchem.2006.08.016 contributor: fullname: Langer, J – volume: 42 start-page: 5120 year: 2003 ident: WOS:000186550800001 article-title: Nickel-catalyzed coupling of carbonyl compounds and Alkynes or 1,3-dienes: An efficient method for the preparation of allylic, homoallylic, and bishomoallylic alcohols publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200301673 contributor: fullname: Ikeda, S – volume: 128 start-page: 2166 year: 2006 ident: WOS:000235562900006 article-title: Eight-membered ring construction by [4+2+2] annulation involving beta-carbon elimination publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0552895 contributor: fullname: Murakami, M – volume: 126 start-page: 3698 year: 2004 ident: WOS:000220440400014 article-title: Ligand-dependent scope and divergent mechanistic behavior in nickel-catalyzed reductive couplings of aldehydes and alkynes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja049644n contributor: fullname: Mahandru, GM – volume: 73 start-page: 2641 year: 2008 ident: WOS:000254544800019 article-title: Nickel-catalyzed cycloadditions of unsaturated hydrocarbons, aldehydes, and ketones publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo702508w contributor: fullname: Tekavec, TN – volume: 126 start-page: 4130 year: 2004 ident: WOS:000220637100040 article-title: Alkene-directed, nickel-catalyzed alkyne coupling reactions publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0491735 contributor: fullname: Miller, KM – start-page: 2697 year: 2006 ident: WOS:000240187000013 article-title: Five- and six-membered nickelacyclic carboxylates as reagents for the facile synthesis of delta-ketocarboxylic acids, isocoumarins, and 1,3-dicarbonyl derivatives of benzoic acid publication-title: SYNTHESIS-STUTTGART doi: 10.1055/s-2006-942507 contributor: fullname: Langer, J – volume: 44 start-page: 2232 year: 2005 ident: WOS:000228415900010 article-title: Remarkably stable (Me3Al)(2)center dot DABCO and stereoselective nickel-catalyzed AlR3 (R = Me, Et) additions to aldehydes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200462569 contributor: fullname: Biswas, K – volume: 7 start-page: 3077 year: 2005 ident: WOS:000230213100069 article-title: Highly regioselective, catalytic asymmetric reductive coupling of 1,3-enynes and ketones publication-title: ORGANIC LETTERS doi: 10.1021/ol051075g contributor: fullname: Miller, KM – volume: 431 start-page: 17 year: 1977 ident: WOS:A1977DK27800002 article-title: NICKEL-HETERO-OLEFIN COMPLEXES WITH HIGH ELECTRON NUMBER publication-title: ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE contributor: fullname: WALTHER, D – volume: 38 start-page: 1166 year: 2009 ident: WOS:000273859200020 article-title: Nickel-catalyzed Reactions between Enone and Two Ethylenes publication-title: CHEMISTRY LETTERS doi: 10.1246/cl.2009.1166 contributor: fullname: Ogoshi, S – volume: 119 start-page: 9065 year: 1997 ident: WOS:A1997XX82000044 article-title: A new stereoselective method for the preparation of allylic alcohols publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Oblinger, E – volume: 132 start-page: 2050 year: 2010 ident: WOS:000275085000070 article-title: Origins of Regioselectivity and Alkene-Directing Effects in Nickel-Catalyzed Reductive Couplings of Alkynes and Aldehydes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja909562y contributor: fullname: Liu, P – volume: 100 start-page: 7426 year: 1996 ident: WOS:A1996UJ11700018 article-title: Molecular geometry of benzaldehyde and salicylaldehyde: A gas-phase electron diffraction and ab initio molecular orbital investigation publication-title: JOURNAL OF PHYSICAL CHEMISTRY contributor: fullname: Borisenko, KB – year: 2010 ident: WOS:000284866000047.51 publication-title: ORG LETT IN PRESS contributor: fullname: OGOSHI S – volume: 43 start-page: 3941 year: 2004 ident: WOS:000223047200013 article-title: Asymmetric catalytic coupling of organoboranes, alkynes, and imines with a removable (trialkylsilyloxy)ethyl group-direct access to enantiomerically pure primary allylic amines publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200460044 contributor: fullname: Patel, SJ – volume: 132 start-page: 6304 year: 2010 ident: WOS:000277445400015 article-title: A General Strategy for Regiocontrol in Nickel-Catalyzed Reductive Couplings of Aldehydes and Alkynes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja102262v contributor: fullname: Malik, HA – volume: 80 start-page: 1115 year: 2008 ident: WOS:000255841500032 article-title: Nickel-catalyzed [2+2+2] cycloaddition of two alkynes and an imine publication-title: PURE AND APPLIED CHEMISTRY doi: 10.1351/pac200880051115 contributor: fullname: Ogoshi, S – volume: 125 start-page: 3442 year: 2003 ident: WOS:000181755800021 article-title: Catalytic asymmetric reductive coupling of alkynes and aldehydes: Enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja034366y contributor: fullname: Miller, KM – volume: 689 start-page: 2952 year: 2004 ident: WOS:000223804300002 article-title: A new set of nickelacyclic carboxylates ("nickelalactones") containing pyridine as supporting ligand: synthesis, structures and application in C-C- and C-S- linkage reactions publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY doi: 10.1016/j.jorganchem.2004.04.047 contributor: fullname: Langer, J – volume: 130 start-page: 14052 year: 2008 ident: WOS:000260301700016 article-title: Nickel-Catalyzed Enantioselective Alkylative Coupling of Alkynes and Aldehydes: Synthesis of Chiral Allylic Alcohols with Tetrasubstituted Olefins publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja805296k contributor: fullname: Yang, Y – volume: 8 start-page: 4441 year: 2006 ident: WOS:000240654700015 article-title: Highly diastereoselective preparation of anti-1,2-diols by catalytic addition of alkynylsilanes to alpha-silyloxyaldehydes publication-title: ORGANIC LETTERS doi: 10.1021/ol061579u contributor: fullname: Sa-ei, K – volume: 436 start-page: 109 year: 1992 ident: WOS:A1992JN41600012 article-title: ACTIVATION OF CO2 ON TRANSITION-METAL CENTERS - COURSE OF HOMOGENEOUS-CATALYTIC FORMATION OF 2-PYRONE FROM CARBON-DIOXIDE AND HEX-3-YNE ON NICKEL(0) FRAGMENTS publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: WALTHER, D – volume: 126 start-page: 11802 year: 2004 ident: WOS:000224103900026 article-title: Direct observation of oxidative Cyclization of eta(2)-alkene and eta(2)-aldehyde on Ni(0) center. Significant acceleration by addition of Me3SiOTf publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0460716 contributor: fullname: Ogoshi, S – volume: 361 start-page: 1381 year: 2008 ident: WOS:000254858200022 article-title: Screening of modular sugar phosphite-oxazoline and phosphite-phosphoroamidite ligand libraries in the asymmetric nickel-catalyzed trialkylaluminium addition to aldehydes publication-title: INORGANICA CHIMICA ACTA doi: 10.1016/j.ica.2007.09.005 contributor: fullname: Mata, Y – volume: 279 start-page: 173 year: 2007 ident: WOS:000250385200008 article-title: Nickel-catalyzed reductive coupling of dienes and carbonyl compounds publication-title: METAL CATALYZED REDUCTIVE C-C BOND FORMATION: A DEPARTURE FROM PREFORMED ORGANOMETALLIC REAGENTS doi: 10.1007/128_2007_121 contributor: fullname: Kimura, M – volume: 127 start-page: 13156 year: 2005 ident: WOS:000232170800038 article-title: Access to macrocyclic endocyclic and exocyclic allylic alcohols by nickel-catalyzed reductive cyclization of ynals publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja054590i contributor: fullname: Knapp-Reed, B – volume: 124 start-page: 2106 year: 2002 ident: WOS:000174469600017 article-title: A new two-step four-component synthesis of highly functionalized cyclohexenols by sequential nickel-catalyzed couplings publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0175845 contributor: fullname: Lozanov, M |
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Snippet | The use of Me2AlOTf as an additive allowed the oxidative cyclization of pivalaldehyde and diphenylacetylene with nickel(0) in the presence of PCy3 to give an... |
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SubjectTerms | Chemistry Chemistry, Inorganic & Nuclear Chemistry, Organic Physical Sciences Science & Technology |
Title | Nickel(0)-Catalyzed Formation of Oxaaluminacyclopentenes via an Oxanickelacyclopentene Key Intermediate: Me2AlOTf-Assisted Oxidative Cyclization of an Aldehyde and an Alkyne with Nickel(0) |
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