Literature DB >> 15040740

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

Rieko Sawaki1, Yoshihiro Sato, Miwako Mori.   

Abstract

Synthetic methods of highly stereocontrolled E- and Z-allylsilanes were developed. When a toluene solution of diene having a silicon moiety and aldehyde was refluxed in the presence of silane using a catalytic amount of Ni(cod)(2) bearing PPh(3), E-allylsilane was obtained in high yield. On the other hand, when the reaction was carried out in THF upon heating in the presence of Ni(cod)(2), imidazolium salt, Cs(2)CO(3), and PPh(3), Z-allylsilane was formed as a sole product.

Entities:  

Year:  2004        PMID: 15040740     DOI: 10.1021/ol049908a

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 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.  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

3.  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

4.  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

5.  Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes.

Authors:  Jichao Xiao; John Montgomery
Journal:  ACS Catal       Date:  2022-02-03       Impact factor: 13.700

Review 6.  Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Authors:  Michael Holmes; Leyah A Schwartz; Michael J Krische
Journal:  Chem Rev       Date:  2018-06-13       Impact factor: 60.622

7.  Access to stereodefined (Z)-allylsilanes and (Z)-allylic alcohols via cobalt-catalyzed regioselective hydrosilylation of allenes.

Authors:  Chao Wang; Wei Jie Teo; Shaozhong Ge
Journal:  Nat Commun       Date:  2017-12-22       Impact factor: 14.919

  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.