Issue 60, 2016

Gold-catalyzed intermolecular formal (3+2) cycloaddition of stabilized vinyldiazo derivatives and electronically unbiased allenes

Abstract

The reaction of electronically unbiased allenes with alkenyldiazo compounds in the presence of gold catalysts provided alkylidenecyclopentene derivatives resulting from a formal intermolecular (3+2) carbocyclization. A stepwise mechanism involving initial activation of the diazo component and subsequent formation of an allyl cation intermediate has been proposed. This process represents the first intermolecular gold-catalyzed cycloaddition involving non-activated allenes.

Graphical abstract: Gold-catalyzed intermolecular formal (3+2) cycloaddition of stabilized vinyldiazo derivatives and electronically unbiased allenes

Supplementary files

Article information

Article type
Communication
Submitted
16 May 2016
Accepted
29 Jun 2016
First published
29 Jun 2016

Chem. Commun., 2016,52, 9398-9401

Gold-catalyzed intermolecular formal (3+2) cycloaddition of stabilized vinyldiazo derivatives and electronically unbiased allenes

E. López, G. Lonzi, J. González and L. A. López, Chem. Commun., 2016, 52, 9398 DOI: 10.1039/C6CC04106J

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