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Short communication: An alternative and effective catalyst in the stereo‐specific reaction of Z ‐1‐aryl‐1‐stannyl‐2‐silylethenes with allyl bromide
Author(s) -
Nakano Taichi,
Kawai Kenji,
Endoh Takanori,
Osada Shintaro,
Miyamoto Takashi
Publication year - 2005
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.957
Subject(s) - chemistry , aryl , bromide , iodide , catalysis , trimethylsilyl , medicinal chemistry , allyl bromide , dimethylformamide , organic chemistry , polymer chemistry , alkyl , solvent
Abstract The Pd(dba) 2 ‐catalyzed reaction of Z ‐1‐aryl‐1‐(tributylstannyl)‐2‐(trimethylsilyl)ethenes with allyl bromide in the presence of copper(I) iodide is reported for the first time. The reaction in the presence of 0.5 mol% Pd(dba) 2 and 8 mol% CuI in dimethylformamide takes place at room temperature to give E ‐2‐aryl‐1‐(trimethylsilyl)penta‐1,4‐dienes exclusively in isolated yields of 62–99%. A putative reaction mechanism is proposed. Copyright © 2005 John Wiley & Sons, Ltd.