Copper-Catalyzed Reaction of α-Aryldiazoesters with Terminal Alkynes: A Formal [3 + 2] Cycloaddition Route Leading to Indene Derivatives
- 24 December 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (51) , 17268-17269
- https://doi.org/10.1021/ja808080h
Abstract
It was discovered that Cu(IPr)Cl-catalyzed reaction of terminal alkynes with α-aryldiazoacetates provides indene derivatives, formal [3 + 2] cycloaddition adducts. Excellent regio- and chemoselectivity were observed to afford either 3H- or 1H-indene esters depending on the reaction conditions employed. The reaction is proposed to proceed via tandem processes: alkyne insertion into copper-carbenoid, intramolecular electrophilic attack on the aromatic ring, and then isomerization.Keywords
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