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

Org Lett. 2012 Apr 20;14(8):2058-61. doi: 10.1021/ol300579m. Epub 2012 Apr 5.

Authors

Yuto Hashimoto¹, Koji Hirano, Tetsuya Satoh, Fumitoshi Kakiuchi, Masahiro Miura

Affiliation

¹ Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.

PMID: 22480263
DOI: 10.1021/ol300579m

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.