112230-06-5Relevant articles and documents
Chemoselective hydrogenation method catalyzed by Pd/C using diphenylsulfide as a reasonable catalyst poison
Mori, Akinori,Mizusaki, Tomoteru,Miyakawa, Yumi,Ohashi, Eri,Haga, Tomoko,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
, p. 11925 - 11932 (2007/10/03)
While 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-Ph2S 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.
Chemoselective control of hydrogenation among aromatic carbonyl and benzyl alcohol derivatives using Pd/C(en) catalyst
Hattori, Kazuyuki,Sajiki, Hironao,Hirota, Kosaku
, p. 4817 - 4824 (2007/10/03)
The hydrogenolysis of aromatic ketones and aldehydes quite smoothly give the corresponding methylene compounds via the formation of the intermediary benzyl alcohols in the presence of Pd/C as a catalyst. Therefore, it is extremely difficult to isolate the intermediary benzyl alcohol selectively. This paper describes a mild and chemoselective hydrogenation method of an aromatic carbonyl compound to benzyl alcohol using the 10% Pd/C(en) catalyst and its application to the chemoselective deacetoxylation reaction at the benzylic position in the presence of the benzyl alcohol functionality within the molecule.