Literature DB >> 16939275

Nickel-catalyzed coupling of alkenes, aldehydes, and silyl triflates.

Sze-Sze Ng1, Chun-Yu Ho, Timothy F Jamison.   

Abstract

A full account of two recently developed nickel-catalyzed coupling reactions of alkenes, aldehydes, and silyl triflates is presented. These reactions provide either allylic alcohol or homoallylic alcohol derivatives selectively, depending on the ligand employed. These processes are believed to be mechanistically distinct from Lewis acid-catalyzed carbonyl-ene reactions, and several lines of evidence supporting this hypothesis are discussed.

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Year:  2006        PMID： 16939275      PMCID： PMC3148200          DOI： 10.1021/ja062866w

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  45 in total

1.  Asymmetric catalytic coupling of organoboranes, alkynes, and imines with a removable (trialkylsilyloxy)ethyl group--direct access to enantiomerically pure primary allylic amines.

Authors:  Sejal J Patel; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-26       Impact factor: 15.336

2.  Quasi solvent-free enantioselective carbonyl-ene reaction with extremely low catalyst loading.

Authors:  Yu Yuan; Xue Zhang; Kuiling Ding
Journal:  Angew Chem Int Ed Engl       Date:  2003-11-17       Impact factor: 15.336

3.  AlMe3-promoted oxidative cyclization of eta2-alkene and eta2-ketone on nickel(0). Observation of intermediate in methyl transfer process.

Authors:  Sensuke Ogoshi; Mizu Ueta; Tomoya Arai; Hideo Kurosawa
Journal:  J Am Chem Soc       Date:  2005-09-21       Impact factor: 15.419

4.  Mechanistic implications of nickel-catalyzed reductive coupling of aldehydes and chiral 1,6-enynes.

Authors:  Ryan M Moslin; Timothy F Jamison
Journal:  Org Lett       Date:  2006-02-02       Impact factor: 6.005

5.  Highly enantioselective direct reductive coupling of conjugated alkynes and alpha-ketoesters via rhodium-catalyzed asymmetric hydrogenation.

Authors:  Jong-Rock Kong; Ming-Yu Ngai; Michael J Krische
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

6.  Ferrocenylphosphines as new catalysts for Baylis-Hillman reactions.

Authors:  Susana Isabel Pereira; Javier Adrio; Artur M S Silva; Juan Carlos Carretero
Journal:  J Org Chem       Date:  2005-11-25       Impact factor: 4.354

7.  Ligand-switchable directing effects of tethered alkenes in nickel-catalyzed additions to alkynes.

Authors:  Karen M Miller; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

8.  Ferrocenyl monophosphine ligands: synthesis and applications in the Suzuki-Miyaura coupling of aryl chlorides.

Authors:  Colin Baillie; Lixin Zhang; Jianliang Xiao
Journal:  J Org Chem       Date:  2004-10-29       Impact factor: 4.354

9.  Metal-catalyzed silacyclopropanation of mono- and disubstituted alkenes.

Authors:  Jelena Ciraković; Tom G Driver; K A Woerpel
Journal:  J Am Chem Soc       Date:  2002-08-14       Impact factor: 15.419

10.  Highly enantioselective catalytic carbon dioxide incorporation reaction: nickel-catalyzed asymmetric carboxylative cyclization of bis-1,3-dienes.

Authors:  Masanori Takimoto; Yoichi Nakamura; Kaoru Kimura; Miwako Mori
Journal:  J Am Chem Soc       Date:  2004-05-19       Impact factor: 15.419
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  18 in total

1.  Highly selective coupling of alkenes and aldehydes catalyzed by [Ni(NHC){P(OPh)3}]: synergy between a strong sigma donor and a strong pi acceptor.

Authors:  Chun-Yu Ho; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Alpha-olefins as alkenylmetal equivalents in catalytic conjugate addition reactions.

Authors:  Chun-Yu Ho; Hirohisa Ohmiya; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 3.  Catalytic carbonyl addition through transfer hydrogenation: a departure from preformed organometallic reagents.

Authors:  John F Bower; In Su Kim; Ryan L Patman; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Nickel Catalysis: Synergy between Method Development and Total Synthesis.

Authors:  Eric A Standley; Sarah Z Tasker; Kim L Jensen; Timothy F Jamison
Journal:  Acc Chem Res       Date:  2015-04-23       Impact factor: 22.384

5.  Nickel-Catalyzed Coupling Reactions of Alkenes.

Authors:  Sze-Sze Ng; Chun-Yu Ho; Kristin D Schleicher; Timothy F Jamison
Journal:  Pure Appl Chem       Date:  2008       Impact factor: 2.453

6.  Regio- and diastereoselective C-C coupling of α-olefins and styrenes to 3-hydroxy-2-oxindoles by Ru-catalyzed hydrohydroxyalkylation.

Authors:  Eiji Yamaguchi; Jeffrey Mowat; Tom Luong; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336

7.  Formation of C-C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation.

Authors:  John F Bower; Michael J Krische
Journal:  Top Organomet Chem       Date:  2011-01-01       Impact factor: 1.311

8.  Catalytic Addition of Simple Alkenes to Carbonyl Compounds Using Group 10 Metals.

Authors:  Chun-Yu Ho; Kristin D Schleicher; Timothy F Jamison
Journal:  Synlett       Date:  2009-10-01       Impact factor: 2.454

9.  Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level via transfer hydrogenative coupling of allyl acetate: departure from chirally modified allyl metal reagents in carbonyl addition.

Authors:  In Su Kim; Ming-Yu Ngai; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419

Review 10.  Transition-metal-catalyzed laboratory-scale carbon-carbon bond-forming reactions of ethylene.

Authors:  Vaneet Saini; Benjamin J Stokes; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-17       Impact factor: 15.336
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