Synlett 2010(16): 2461-2464  
DOI: 10.1055/s-0030-1258563
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of Conjugated (E)-Enynones via Two Types of Cross-Coupling Reaction

Masayuki Hoshi*, Hirokazu Yamazaki, Mitsuhiro Okimoto
Department of Biotechnology and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, Hokkaido 090-8507, Japan
Fax: +81(157)247719; e-Mail: hoshi-m@chem.kitami-it.ac.jp;
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Publikationsverlauf

Received 14 July 2010
Publikationsdatum:
03. September 2010 (online)

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Abstract

(Trimethylsilyl)ethynyl bromide can be easily transformed into conjugated (E)-enynones, whose skeleton consists of consecutive carbonyl, ethynyl, and (E)-ethenyl units, via a one-pot multicomponent Suzuki-type reaction-Sonogashira reaction sequence. Thus, a three-component coupling of (trimethylsilyl)ethynyl bromide, (E)-alk-1-enyldisiamylborane and acid chloride is achieved in a two-step, one-pot procedure, in which (E)-alk-1-enyl group is installed as nucleophile in the sp-carbon atom attached to bromine atom and acyl group is installed as electrophile in the other sp-carbon atom.