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Issue 70, 2016
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Pd-Catalyzed oxidative isomerization of propargylic acetates: highly efficient access to α-acetoxyenones via alkenyl Csp2–O bond-forming reductive elimination from PdIV

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Abstract

A Pd(II)/(IV)-catalyzed oxidative isomerization of propargylic acetates developed for the synthesis of polysubstituted alkenyl acetates is described. The reductive elimination of alkenyl Csp2–OAc bonds from PdIV intermediates is achieved. Mechanistic studies indicate that the reaction mechanism consists of trans acetoxypalladation of a triple bond, isomerization, oxidative addition with PhI(OAc)2 and alkenyl C–OAc bond reductive elimination.

Graphical abstract: Pd-Catalyzed oxidative isomerization of propargylic acetates: highly efficient access to α-acetoxyenones via alkenyl Csp2–O bond-forming reductive elimination from PdIV

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Submitted
27 May 2016
Accepted
23 Jul 2016
First published
25 Jul 2016

Chem. Commun., 2016,52, 10644-10647
Article type
Communication

Pd-Catalyzed oxidative isomerization of propargylic acetates: highly efficient access to α-acetoxyenones via alkenyl Csp2–O bond-forming reductive elimination from PdIV

J. Li, W. Yang, F. Yan, Q. Liu, P. Wang, Y. Li, Y. Zhao, Y. Dong and H. Liu, Chem. Commun., 2016, 52, 10644
DOI: 10.1039/C6CC04463H

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