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Scope and Selectivity of Heterogeneous Rh 0 ‐Catalyzed Tandem Dehydrocoupling/Hydrogenation Using Me 2 NH·BH 3 as a Stoichiometric H 2 Source
Author(s) -
Sloan Matthew E.,
Staubitz Anne,
Lee Kajin,
Manners Ian
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001332
Subject(s) - chemistry , nitrile , alkene , catalysis , epoxide , tandem , nitro , selectivity , stoichiometry , medicinal chemistry , functional group , chemoselectivity , organic chemistry , combinatorial chemistry , materials science , alkyl , polymer , composite material
The catalytic dehydrocoupling of Me 2 NH · BH 3 ( 1 ) by Rh/Al 2 O 3 ( 2 ) has been shown to act as an efficient hydrogenation and reduction system for a variety of organic substrates. A range of functional groups have been reduced, but chloro, bromo and iodo substituents, epoxide and nitrile groups were found to be stable under the reaction conditions, allowing chemoselective hydrogenation reactions to be performed. This reduction has also been shown to proceed cleanly under atmospheric air for a few representative examples of alkene and nitro functional groups.