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Chemoselective hydrogenation method catalyzed by Pd C using diphenylsulfide as a reasonable catalyst poison

Tetrahedron£¬ Vol 62£¬ (2006), page 11925¨C11932

Akinori Mori, Tomoteru Mizusaki, Yumi Miyakawa, Eri Ohashi, Tomoko Haga,
Tomohiro Maegawa, Yasunari Monguchi and Hironao Sajiki*

Abstract¡ªWhile Pd/C is one of the most useful catalysts for hydrogenation, the high catalyst activity of Pd/C causes difficulty in its application
to chemoselective hydrogenation between different types of reducible functionalities. In order to achieve chemoselective hydrogenation
using Pd/C, we investigated catalyst poison as a controller of the catalyst activity.We found that the addition of Ph2S (diphenylsulfide) to
the Pd/C-catalyzed hydrogenation reaction mixture led to reasonable deactivation of Pd/C. By the use of the Pd/C¨CPh2S catalytic system,
olefins, acetylenes, and azides can be selectively reduced in the coexistence of aromatic carbonyls, aromatic halides, cyano groups, benzyl
esters, and N-Cbz (benzyloxycarbonyl) protecting groups. The present method is promising as a general and practical chemoselective hydrogenation
process in synthetic organic chemistry.

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