Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 5, Pages 1464-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja909145y
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Funding
- Boston University
- Department of Chemistry
- American Chemical Society Petroleum Research [48479-G1]
- NSF [CHE-0619339, CHE-0443618]
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We report the application of visible-light photoredox catalysis for the formation of C-C bonds between tertiary N-arylamines and nitroalkanes via an oxidative aza-Henry reaction. In the presence of I mol % Ir(ppy)(2)(dtbbpy)PF6, efficient coupling of nitroalkanes with in situ-generated iminium ions provides the desired products in up to 96% yield. Mechanistic studies suggest that reductive quenching of the Ir3+ excited state by the tertiary amine leads to the ammonium radical cation, with subsequent catalyst turnover (Ir2+ --> Ir3+) likely effected by atmospheric oxygen.
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