Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 24, Pages 9942-9945Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja304561c
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Funding
- University of Delaware (UD)
- University of Delaware Research Foundation
- NSF [NSF MIR 0421224, NSF CRIF MU CHE0840401]
- NIH [NIH P20 RR017716, NIH S10 RR02692]
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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.
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