Literature DB >> 21814295

Nickel-Catalyzed Coupling Reactions of Alkenes.

Sze-Sze Ng1, Chun-Yu Ho, Kristin D Schleicher, Timothy F Jamison.   

Abstract

Several reactions of simple, unactivated alkenes with electrophiles under nickel(0) catalysis are discussed. The coupling of olefins with aldehydes and silyl triflates provides allylic or homoallylic alcohol derivatives, depending on the supporting ligands and, to a lesser extent, the substrates employed. Reaction of alkenes with isocyanates yields N-alkyl acrylamides. In these methods, alkenes act as the functional equivalents of alkenyl- and allylmetal reagents.

Entities:  

Year:  2008        PMID: 21814295      PMCID: PMC3148197          DOI: 10.1351/pac200880050929

Source DB:  PubMed          Journal:  Pure Appl Chem        ISSN: 0033-4545            Impact factor:   2.453


  27 in total

1.  Asymmetric hydrovinylation reaction.

Authors:  T V RajanBabu
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  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

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.  Highly selective catalytic intermolecular reductive coupling of alkynes and aldehydes

Authors: 
Journal:  Org Lett       Date:  2000-12-28       Impact factor: 6.005

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

Authors:  Sze-Sze Ng; Chun-Yu Ho; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2006-09-06       Impact factor: 15.419

6.  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

7.  Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones.

Authors:  Karen M Miller; Wei-Sheng Huang; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2003-03-26       Impact factor: 15.419

8.  Elucidating reactivity differences in palladium-catalyzed coupling processes: the chemistry of palladium hydrides.

Authors:  Ivory D Hills; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2004-10-20       Impact factor: 15.419

9.  cis-stereoselective nickel-catalyzed cyclization/alkylation and arylation reactions of allenyl-aldehydes and -ketones with organozinc reagents.

Authors:  Suk-Ku Kang; Seok-Keun Yoon
Journal:  Chem Commun (Camb)       Date:  2002-11-21       Impact factor: 6.222

10.  Ligand-controlled highly stereoselective syntheses of e- and z-allylsilanes from dienes and aldehydes using nickel complex.

Authors:  Rieko Sawaki; Yoshihiro Sato; Miwako Mori
Journal:  Org Lett       Date:  2004-04-01       Impact factor: 6.005

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  16 in total

1.  Nickel-catalyzed allylic substitution of simple alkenes.

Authors:  Ryosuke Matsubara; Timothy F Jamison
Journal:  Chem Asian J       Date:  2011-03-08

2.  Nickel-catalyzed allylic substitution of simple alkenes.

Authors:  Ryosuke Matsubara; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2010-05-26       Impact factor: 15.419

3.  A Highly Chemo-, Regio-, and Stereoselective Metallacycle-Mediated Annulation Between a Conjugated Enyne and an Ene-Diyne.

Authors:  Zachary A Shalit; Glenn C Micalizio
Journal:  ARKIVOC       Date:  2018-03-28       Impact factor: 1.140

4.  Concerning the potential reversibility of carbometalation in alkoxide-directed Ti(Oi-Pr)4-mediated reductive cross-coupling of homoallylic alcohols with aromatic imines.

Authors:  Masayuki Takahashi; Glenn C Micalizio
Journal:  Chem Commun (Camb)       Date:  2010-04-08       Impact factor: 6.222

5.  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

6.  Nickel-catalyzed cycloaddition of 1,3-dienes with 3-azetidinones and 3-oxetanones.

Authors:  Ashish Thakur; Megan E Facer; Janis Louie
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-23       Impact factor: 15.336

7.  Tunable Phosphoramidite Ligands for Asymmetric Hydrovinylation: Ligands par excellence for Generation of All-Carbon Quaternary Centers.

Authors:  Craig R Smith; Hwan Jung Lim; Aibin Zhang; T V Rajanbabu
Journal:  Synthesis (Stuttg)       Date:  2009-01-01       Impact factor: 3.157

8.  Origins of regioselectivity and alkene-directing effects in nickel-catalyzed reductive couplings of alkynes and aldehydes.

Authors:  Peng Liu; Patrick McCarren; Paul Ha-Yeon Cheong; Timothy F Jamison; K N Houk
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

9.  Mechanism and transition-state structures for nickel-catalyzed reductive alkyne-aldehyde coupling reactions.

Authors:  P R McCarren; Peng Liu; Paul Ha-Yeon Cheong; Timothy F Jamison; K N Houk
Journal:  J Am Chem Soc       Date:  2009-05-20       Impact factor: 15.419

10.  One-pot multicomponent coupling methods for the synthesis of diastereo- and enantioenriched (Z)-trisubstituted allylic alcohols.

Authors:  Michael H Kerrigan; Sang-Jin Jeon; Young K Chen; Luca Salvi; Patrick J Carroll; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2009-06-24       Impact factor: 15.419

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