Benzylation of nitroalkanes using copper-catalyzed thermal redox catalysis: toward the facile C-alkylation of nitroalkanes.
The C-alkylation of nitroalkanes under mild conditions has been a significant challenge in organic synthesis for more than a century. Herein we report a simple Cu(I) catalyst, generated in situ, that is highly effective for C-benzylation of nitroalkanes using abundant benzyl bromides and related heteroaromatic compounds. This process, which we believe proceeds via a thermal redox mechanism, allows access to a variety of complex nitroalkanes under mild reaction conditions and represents the first step toward the development of a general catalytic system for the alkylation of nitroalkanes.
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.
Peter G
PG
Gildner
Amber A S
AA
Gietter
Di
D
Cui
Donald A
DA
Watson
D000473:Alkanes / Q000737:chemistry*; D000478:Alkylation; D001554:Benzene / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction
D000473:Alkanes; D009574:Nitro Compounds; D003300:Copper; D001554:Benzene