Synthesis 2019; 51(24): 4619-4624
DOI: 10.1055/s-0039-1690207
paper
© Georg Thieme Verlag Stuttgart · New York

Regioselective Diboron-Mediated Semireduction of Terminal Allenes

Ashley M. Gates
,
Department of Chemistry, Virginia Tech, Blacksburg, VA 24061, USA   Email: santosw@vt.edu
› Author Affiliations
We acknowledge financial support by the National Science Foundation (CHE-1414458) and funds to purchase the Inova-400 NMR (CHE-0131124) and Agilent 6220 Accurate Mass TOF LC/MS spectrometers (CHE-0722638).
Further Information

Publication History

Received: 18 August 2019

Accepted after revision: 11 September 2019

Publication Date:
10 October 2019 (online)

Abstract

A method for the regioselective reduction of the terminal double bond of 1,1-disubstituted allenes has been developed. In the presence of a palladium catalyst, tetrahydroxydiboron and stoichiometric water, allene semireduction proceeds in high yield to afford Z-alkenes selectively.

Supporting Information

 
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