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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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Publication details

The article was received on 27 May 2016, accepted on 23 Jul 2016 and first published on 25 Jul 2016


Article type: Communication
DOI: 10.1039/C6CC04463H
Chem. Commun., 2016,52, 10644-10647

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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

    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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