Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization

被引：734

作者：

Condie, Allison G. ^{[1
]}

Gonzalez-Gomez, Jose C. ^{[1
]}

Stephenson, Corey R. J. ^{[1
]}

机构：

[1] Boston Univ, Dept Chem, Boston, MA 02215 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 05期

关键词：

OXIDATIVE CYANATION; TERTIARY-AMINES; HYDROGEN-PEROXIDE; MOLECULAR-OXYGEN; BOND; PHOTOCHEMISTRY; PHOTOPHYSICS; COMPLEXES; ALKYLATION; ALDEHYDES;

D O I：

10.1021/ja909145y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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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页码：1464 / +

页数：4

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