Ruthenium(II)-catalyzed regio- and stereoselective hydroarylation of alkynes via directed C-H functionalization

Yuto Hashimoto; Koji Hirano; Tetsuya Satoh; Fumitoshi Kakiuchi; Masahiro Miura

doi:10.1021/ol300579m

Ruthenium(II)-catalyzed regio- and stereoselective hydroarylation of alkynes via directed C-H functionalization

Yuto Hashimoto, Koji Hirano, Tetsuya Satoh, Fumitoshi Kakiuchi, Masahiro Miura

Department of Chemistry

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

118 Citations (Scopus)

Abstract

The ruthenium-catalyzed hydroarylation of alkynes with benzamides proceeds regio- and stereoselectively through a directed C-H bond cleavage. Preliminary mechanistic investigations indicate that the reaction involves amide-directed ortho-metalation, carbometalation of alkyne, and protonolysis. Similarly, phenylazoles also add to alkynes regioselectively.

Original language	English
Pages (from-to)	2058-2061
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	8
DOIs	https://doi.org/10.1021/ol300579m
Publication status	Published - 2012 Apr 20

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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AU - Hirano, Koji

AU - Satoh, Tetsuya

AU - Kakiuchi, Fumitoshi

AU - Miura, Masahiro

PY - 2012/4/20

Y1 - 2012/4/20

N2 - The ruthenium-catalyzed hydroarylation of alkynes with benzamides proceeds regio- and stereoselectively through a directed C-H bond cleavage. Preliminary mechanistic investigations indicate that the reaction involves amide-directed ortho-metalation, carbometalation of alkyne, and protonolysis. Similarly, phenylazoles also add to alkynes regioselectively.

AB - The ruthenium-catalyzed hydroarylation of alkynes with benzamides proceeds regio- and stereoselectively through a directed C-H bond cleavage. Preliminary mechanistic investigations indicate that the reaction involves amide-directed ortho-metalation, carbometalation of alkyne, and protonolysis. Similarly, phenylazoles also add to alkynes regioselectively.

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Ruthenium(II)-catalyzed regio- and stereoselective hydroarylation of alkynes via directed C-H functionalization

Abstract

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