A direct synthesis of allenes by a traceless petasis reaction

Devon A. Mundal; Kelly E. Lutz; Regan J. Thomson

doi:10.1021/ja301489n

A direct synthesis of allenes by a traceless petasis reaction

Devon A. Mundal, Kelly E. Lutz, Regan J. Thomson^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

58 Scopus citations

Abstract

A one-pot synthesis of allenes by the 2-nitrobenzenesulfonylhydrazide- mediated coupling of hydroxyaldehydes or ketones with alkynyl trifluoroborate salts is reported. This mild process involves in situ formation of a sulfonylhydrazone that reacts with alkynyl trifluoroborates to generate a transient propargylic hydrazide species. Decomposition of this unstable hydrazide via an intermediate monoalkyldiazine produces the allene products through an alkene walk mechanism.

Original language	English (US)
Pages (from-to)	5782-5785
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	134
Issue number	13
DOIs	https://doi.org/10.1021/ja301489n
State	Published - Apr 4 2012

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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