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Synfacts 2009(11): 1287-1287  
DOI: 10.1055/s-0029-1218067
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Nitriles from Primary Alcohols and NH3 with Ru(OH)x/Al2O3

Contributor(s):Yasuhiro Uozumi, Go Hamasaka
T. Oishi, K. Yamaguchi, N. Mizuno*
The University of Tokyo and Science and Technology Agency, Saitama, Japan
Catalytic Oxidative Synthesis of Nitriles Directly from Primary Alcohols and Ammonia
Angew. Chem. Int. Ed.  2009,  48:  6286-6288  
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Publication History

Publication Date:
22 October 2009 (online)

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Key words

nitriles - primary alcohols - ammonia - ruthenium - aluminum oxide

Significance

An Al2O3-supported ruthenium ­hydroxide catalyst (Ru(OH)x/Al2O3) promoted the reaction of primary alcohols 1 or aldehydes 2 with ammonia to give the corresponding nitriles 3 in 65-96% yield (from 1, 13 examples; from 2, 7 ­examples). No leaching of ruthenium was observed by ICP-AES analysis after the reaction.

Comment

The authors have previously reported the preparation and characterization of Ru(OH)x/Al2O3 and its application to the aerobic oxidative dehydrogenation of alcohols (Angew. Chem. Int. Ed. 2002, 41, 4538; Chem. Eur. J. 2003, 9, 4353). The catalytic activity of Ru(OH)x/Al2O3 was superior to that of the other supported catalysts for the formation of 3a from 1a [Au(OH)x/Al2O3: 10%, Pd(OH)x/Al2O3: <1%, Pt(OH)x/Al2O3: <1%, Rh(OH)x/Al2O3: <1%, Ru/C: 22%, RuHAP: 4%].

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