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. 2013 May 14;49(39):4376-8.
doi: 10.1039/c2cc34609e. Epub 2012 Aug 3.

Ring expansion of alkynyl cyclopropanes to highly substituted cyclobutenes via a N-sulfonyl-1,2,3-triazole intermediate

Renhe Liu  1 , Min Zhang, Gabrielle Winston-McPherson, Weiping Tang
Affiliations

Ring expansion of alkynyl cyclopropanes to highly substituted cyclobutenes via a N-sulfonyl-1,2,3-triazole intermediate

Renhe Liu et al. Chem Commun (Camb). .

Abstract

Regioselective ring expansion of alkynyl cyclopropanes to highly substituted cyclobutenes was developed. The reaction involves a copper-catalyzed cycloaddition of an alkyne with an arylsulfonyl azide and a silver-catalyzed carbene formation followed by ring expansion of a cyclopropyl carbene intermediate.

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Figures

Scheme 1
Scheme 1
Ring Expansion of Cyclopropyl Metal Carbene
Scheme 2
Scheme 2
Preparation of Substituted Cyclopropanes from Alkenes
Scheme 3
Scheme 3
Effect of Catalysts on the Regioselectivity of Ring Expansion
Scheme 4
Scheme 4
Effect of Azides on Ring Expansion
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