Simple, chemoselective hydrogenation with thermodynamic stereocontrol

Kotaro Iwasaki; Kanny K. Wan; Alberto Oppedisano; Steven W.M. Crossley; Ryan A. Shenvi

doi:10.1021/ja412342g

Simple, chemoselective hydrogenation with thermodynamic stereocontrol

Kotaro Iwasaki, Kanny K. Wan, Alberto Oppedisano, Steven W.M. Crossley, Ryan A. Shenvi

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

183 Citations (Scopus)

Abstract

Few methods permit the hydrogenation of alkenes to a thermodynamically favored configuration when steric effects dictate the alternative trajectory of hydrogen delivery. Dissolving metal reduction achieves this control, but with extremely low functional group tolerance. Here we demonstrate a catalytic hydrogenation of alkenes that affords the thermodynamic alkane products with remarkably broad functional group compatibility and rapid reaction rates at standard temperature and pressure.

Original language	English
Pages (from-to)	1300-1303
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	4
DOIs	https://doi.org/10.1021/ja412342g
Publication status	Published - 2014 Jan 29
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja412342g

Cite this

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AU - Wan, Kanny K.

AU - Oppedisano, Alberto

AU - Crossley, Steven W.M.

AU - Shenvi, Ryan A.

PY - 2014/1/29

Y1 - 2014/1/29

N2 - Few methods permit the hydrogenation of alkenes to a thermodynamically favored configuration when steric effects dictate the alternative trajectory of hydrogen delivery. Dissolving metal reduction achieves this control, but with extremely low functional group tolerance. Here we demonstrate a catalytic hydrogenation of alkenes that affords the thermodynamic alkane products with remarkably broad functional group compatibility and rapid reaction rates at standard temperature and pressure.

AB - Few methods permit the hydrogenation of alkenes to a thermodynamically favored configuration when steric effects dictate the alternative trajectory of hydrogen delivery. Dissolving metal reduction achieves this control, but with extremely low functional group tolerance. Here we demonstrate a catalytic hydrogenation of alkenes that affords the thermodynamic alkane products with remarkably broad functional group compatibility and rapid reaction rates at standard temperature and pressure.

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Simple, chemoselective hydrogenation with thermodynamic stereocontrol

Abstract

ASJC Scopus subject areas

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