Intermolecular Nonreductive Alkylation of Enamides via Radical−Polar Crossover

Gregory K Friestad; Yaoping Wu

doi:10.1021/ol8028077

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Intermolecular Nonreductive Alkylation of Enamides via Radical−Polar Crossover

Journal article

Peer reviewed

Intermolecular Nonreductive Alkylation of Enamides via Radical−Polar Crossover

Gregory K Friestad and Yaoping Wu

Organic letters, Vol.11(4), pp.819-822

02/19/2009

DOI: 10.1021/ol8028077

PMID: 19199766

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Abstract

A carbon−carbon bond construction method is disclosed which involves radical addition of α-haloesters or iodoacetonitrile to enamides. Despite the presence of tri-n-butylstannane, nonreductive addition was predominant; H-atom transfer from tin hydride was not observed. Rapid iodine atom transfer to (or electron transfer from) the radical adduct, resulting in an iminium ion intermediate and radical chain propagation, is consistent with the observed reactivity.

Details

Title: Subtitle: Intermolecular Nonreductive Alkylation of Enamides via Radical−Polar Crossover
Creators: Gregory K Friestad
Yaoping Wu
Resource Type: Journal article
Publication Details: Organic letters, Vol.11(4), pp.819-822
Publisher: American Chemical Society
DOI: 10.1021/ol8028077
PMID: 19199766
ISSN: 1523-7060
eISSN: 1523-7052
Language: English
Date published: 02/19/2009
Academic Unit: Chemistry
Record Identifier: 9983985889502771

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