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Literature DB >> 16218608

Simple alkenes as substitutes for organometallic reagents: nickel-catalyzed, intermolecular coupling of aldehydes, silyl triflates, and alpha olefins.

Abstract

A nickel-catalyzed method for the three-component coupling of alkenes (ethylene and alpha olefins), aldehydes, and silyl triflates is described, and this process represents the first catalytic method for coupling aldehydes and alkenes to give allylic alcohol derivatives. Conceptually, the alkene functions as a replacement for an alkenylmetal reagent.

Entities: Chemical

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Year: 2005 PMID： 16218608 DOI： 10.1021/ja055363j

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

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Cited

21 in total

1. Nickel-catalyzed Heck-type reactions of benzyl chlorides and simple olefins.

Authors: Ryosuke Matsubara; Alicia C Gutierrez; Timothy F Jamison
Journal: J Am Chem Soc Date: 2011-11-08 Impact factor: 15.419

2. 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

3. Nickel-catalyzed, carbonyl-ene-type reactions: selective for alpha olefins and more efficient with electron-rich aldehydes.

Authors: Chun-Yu Ho; Sze-Sze Ng; Timothy F Jamison
Journal: J Am Chem Soc Date: 2006-04-26 Impact factor: 15.419

10. 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

Simple alkenes as substitutes for organometallic reagents: nickel-catalyzed, intermolecular coupling of aldehydes, silyl triflates, and alpha olefins.

1. Nickel-catalyzed Heck-type reactions of benzyl chlorides and simple olefins.

2. 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.

3. Nickel-catalyzed, carbonyl-ene-type reactions: selective for alpha olefins and more efficient with electron-rich aldehydes.

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

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

6. Nickel-Catalyzed Coupling Reactions of Alkenes.

7. Nickel-catalyzed allylic substitution of simple alkenes.

8. Nickel-catalyzed allylic substitution of simple alkenes.

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

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