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A novel synthesis of haloalkenes from aldehydes with carbon-carbon coupling

✍ Scribed by Tsuyoshi Satoh; Norifumi Itoh; Ken-ichi Onda; Yasushi Kitoh; Koji Yamakawa

Book ID: 104224721
Publisher: Elsevier Science
Year: 1992
Tongue: French
Weight: 136 KB
Volume: 33
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)91653-8

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✦ Synopsis

Haloalkenes are interesting cumpuunds in organic chctnistry.l In particular, tluoroalkenes have received much attcntivn as non-hydrolizable amide ii;oslers. 2 Recently. we reported a new synthesis nf tr-halo kerones from aldehydes and l-halo&y1 aryl sulfoxides via erhyhnagnesium bromide mediated dcsulfinylntinn of n-halo fi-ketn sulfoxides 3 This reaction was proved to take place by the attack of a carbanion to the sulfinyl group (ligand exchange reaction of sulfoxide4).

We thought that a similar reaction would take place with a-halo P-mesyloxy sulfoxides 2. In this paper, we report the n-B&i medialed desulfinylation of *-halo fi-mesyloxy sulfoxides 2, easily derived from 1 and aldehydes, giving fluoroalkenes 3 (X=F) and chloroalkenes 3 (X=Cl) in high yields (Scheme I).

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