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Issue 5, 2014
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Synthesis of heterocycles via transition-metal-catalyzed hydroarylation of alkynes

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Abstract

Transition-metal (TM)-catalyzed hydroarylation reactions of alkynes have received much attention, because they enable the net insertion of alkyne C–C triple bonds into C–H bonds of aromatic precursors, resulting in regio- and stereo-selective formation of synthetically useful arylalkenes. Taking advantage of this feature, TM-catalyzed alkyne hydroarylations have been successfully used for the synthesis of heterocycles. TM-catalyzed alkyne hydroarylations can be classified into three major categories depending on the type of reaction and precursors involved: (1) palladium-catalyzed reductive Heck reactions of alkynes with aryl halides, (2) TM-catalyzed conjugate arylation reactions of activated alkynes with arylboronic acids, and (3) TM-catalyzed aromatic C–H alkenylations with alkynes. This review surveys heterocycle synthesis via TM-catalyzed hydroarylation of alkynes according to the above classification, with an emphasis on the scope and limitations, as well as the underlying mechanisms.

Graphical abstract: Synthesis of heterocycles via transition-metal-catalyzed hydroarylation of alkynes

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Publication details

The article was received on 16 Oct 2013 and first published on 16 Dec 2013


Article type: Review Article
DOI: 10.1039/C3CS60369E
Chem. Soc. Rev., 2014,43, 1575-1600

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    Synthesis of heterocycles via transition-metal-catalyzed hydroarylation of alkynes

    Y. Yamamoto, Chem. Soc. Rev., 2014, 43, 1575
    DOI: 10.1039/C3CS60369E

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