Copper-Catalyzed Reaction of α-Aryldiazoesters with Terminal Alkynes: A Formal [3 + 2] Cycloaddition Route Leading to Indene Derivatives

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 employ...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2008-12, Vol.130 (51), p.17268-17269
Main Authors: Park, Eun Ju, Kim, Seok Hwan, Chang, Sukbok
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja808080h