Coupling reaction of alkyl chlorides with silyl enolates catalyzed by indium trihalide

Yoshihiro Nishimoto; Makoto Yasuda; Akio Baba

doi:10.1021/ol701684n

Coupling reaction of alkyl chlorides with silyl enolates catalyzed by indium trihalide

Org Lett. 2007 Nov 22;9(24):4931-4. doi: 10.1021/ol701684n. Epub 2007 Nov 2.

Authors

Yoshihiro Nishimoto¹, Makoto Yasuda, Akio Baba

Affiliation

¹ Department of Applied Chemistry, Center for Atomic and Molecular Technologies (CAMT), Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.

PMID: 17975916
DOI: 10.1021/ol701684n

Abstract

Indium(III) halide catalyzed not only the coupling of alkyl chlorides with silyl enolates derived from esters, ketones, and aldehydes to give a variety of alpha-alkylated carbonyl compounds but also one-pot, three-component reactions of aldehyde enolate, alkyl chloride, and allylsilane or alkynylsilane.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemical synthesis
Aldehydes / chemistry
Amides / chemical synthesis
Amides / chemistry
Bromides / chemistry*
Catalysis
Esters / chemical synthesis
Esters / chemistry
Hydrocarbons, Chlorinated / chemistry*
Indium / chemistry*
Ketones / chemical synthesis
Ketones / chemistry
Molecular Structure
Silanes / chemistry*
Stereoisomerism

Substances

Aldehydes
Amides
Bromides
Esters
Hydrocarbons, Chlorinated
Ketones
Silanes
Indium