TY - JOUR
T1 - Novel carbon-carbon bond-forming reactions using carbocations produced from substituted propargyl silyl ethers by the action of TMSOTf
AU - Ishikawa, T.
AU - Okano, M.
AU - Aikawa, T.
AU - Saito, S.
PY - 2001/6/29
Y1 - 2001/6/29
N2 - Highly useful carbon-carbon bond forming reactions using stable allenyl, propargyl, or allyl-propargyl hybrid cations have been developed. These carbocations could be generated from silyl 1-(π-donor)-substituted propargyl ethers by the action of trimethylsilyl trifluoromethanesulfonate in dichloromethane at -78 °C to room temperature and could be attacked nucleophilically by electron rich arenes, allylsilanes, or enol silyl ethers, giving rise to allenes, alkynes, and their derivatives. A novel method for regio- and stereoselective synthesis of conjugated enynes utilizing allyl-propargyl hybrid cations has also been established.
AB - Highly useful carbon-carbon bond forming reactions using stable allenyl, propargyl, or allyl-propargyl hybrid cations have been developed. These carbocations could be generated from silyl 1-(π-donor)-substituted propargyl ethers by the action of trimethylsilyl trifluoromethanesulfonate in dichloromethane at -78 °C to room temperature and could be attacked nucleophilically by electron rich arenes, allylsilanes, or enol silyl ethers, giving rise to allenes, alkynes, and their derivatives. A novel method for regio- and stereoselective synthesis of conjugated enynes utilizing allyl-propargyl hybrid cations has also been established.
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U2 - 10.1021/jo010157p
DO - 10.1021/jo010157p
M3 - Article
C2 - 11421785
AN - SCOPUS:0035967754
SN - 0022-3263
VL - 66
SP - 4635
EP - 4642
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 13
ER -