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Stereospecific synthesis of a family of novel ( E )‐2‐aryl‐1‐silylalka‐1,4‐dienes or ( E )‐4‐aryl‐5‐silylpenta‐1,2,4‐trienes via a cross‐coupling of ( Z )‐silyl(stannyl)ethenes with allyl halides or propargyl bromide
Author(s) -
Sasaki Fumio,
Endo Takanori,
Noguchi Masanori,
Kawai Kenji,
Nakano Taichi
Publication year - 2008
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.1360
Subject(s) - chemistry , aryl , stereospecificity , bromide , propargyl bromide , silylation , propargyl , iodide , medicinal chemistry , halide , coupling reaction , allyl bromide , catalysis , stereochemistry , organic chemistry , alkyl
Stereospecific synthesis of a family of novel ( E )‐2‐aryl‐1‐silylalka‐1,4‐dienes or ( E )‐4‐aryl‐5‐silylpenta‐1,2,4‐trienes via a cross‐coupling of ( Z )‐silyl(stannyl)ethenes with allyl halides or propargyl bromide is described. In the reaction with allyl bromide, either a Pd(dba) 2 CuI combination (dba, dibenzylideneacetone) in DMF or copper(I) iodide in DMSO–THF readily catalyzes or mediates the coupling reaction of ( Z )‐silyl(stannyl)ethenes at room temperature, producing novel vinylsilanes bearing an allyl group β to silicon with cis ‐disposition in good yields. Allyl chlorides as halides can be used in the CuI‐mediated reaction. CuI alone much more effectively mediates the cross‐coupling reaction with propargyl bromide in DMSO–THF at room temperature compared with a Pd(dba) 2 CuI combination catalysis in DMF, providing novel stereodefined vinylsilanes bearing an allenyl group β to silicon with cis ‐disposition in good yields. Copyright © 2008 John Wiley & Sons, Ltd.