Efficient Catalytic Insertion of Acetylenes into a Carbon−Carbon Single Bond of Nonstrained Cyclic Compounds under Mild Conditions
- 15 August 2006
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (35), 11368-11369
- https://doi.org/10.1021/ja064022i
Abstract
A rhenium complex, [ReBr(CO)3(thf)]2, catalyzes the reaction of a 1,3-dicarbonyl cyclic compound with an acetylene to give a medium-sized cyclic compound in excellent yield. By using isocyanide as an additive, the catalytic activity of the rhenium complex changes dramatically, and the insertion of acetylenes into a carbon−carbon single bond occurs under mild conditions. A plausible mechanism is that the reaction proceeds via the formation of a rhenacyclopentene intermediate, ring opening by a retro-aldol reaction, isomerization, and reductive elimination.This publication has 25 references indexed in Scilit:
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