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Indium(III) Chloride/Chlorotrimethylsilane as a Highly Active Lewis Acid Catalyst System for the Sakurai−Hosomi Reaction
Author(s) -
Onishi Yoshiyuki,
Ito Takeshi,
Yasuda Makoto,
Baba Akio
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200205)2002:9<1578::aid-ejoc1578>3.0.co;2-p
Subject(s) - chemistry , lewis acids and bases , catalysis , regioselectivity , indium , chloride , lewis acid catalysis , organic chemistry , medicinal chemistry , polymer chemistry
The indium(III) chloride/chlorotrimethylsilane system acts as a catalyst for the Sakurai−Hosomi reaction between allylsilanes and aldehydes. When γ‐substituted allylsilanes such as crotylsilane and prenylsilane are used a high regioselectivity for γ‐addition is observed. Smaller amounts of the catalyst (5 mol %) effectively afforded the allylation products, although larger amounts (20 mol %) gave no product whatsoever. Other group 13 Lewis acids such as AlCl 3 and BF 3 ·OEt 2 did not have catalytic activity even when combined with chlorotrimethylsilane. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)