Journal
CHIMIA
Volume 66, Issue 6, Pages 413-417Publisher
SWISS CHEMICAL SOC
DOI: 10.2533/chimia.2012.413
Keywords
CH-amination; N-Oxoammonium salts; Oxidative coupling; 2,2,6,6-Tetramethylpiperidine-N-oxyl radical (TEMPO); Transition-metal-free
Categories
Funding
- Deutsche Forschungsgemeinschaft [SFB 858]
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The application of nitroxides for the development of new synthetic methods and their implementation in polymer chemistry, material science and beyond is one of the major research topics in our laboratory in the institute of organic chemistry at the WWU Munster. This short review focuses on our recent progress towards nitroxide-based transition-metal-free oxidative coupling reactions. The demand for organic surrogates for transition metals in such transformations is in our eyes unquestionable, since environmental and economic issues have become progressively more important in recent years. For this purpose, the 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO) is shown to be a highly efficient oxidant for the homo- and cross-coupling of Grignard reagents. This powerful C-C bond forming strategy allows the generation of conjugated polymers from bifunctional Grignard reagents. Moreover, cross-coupling of alkynyl Grignard compounds and nitrones can be accomplished under aerobic atmosphere with catalytic amounts of TEMPO. It is also shown that TEMPO-derived N-oxoammonium salts can act as suitable oxidants for formation of C-N bonds between non-preactivated benzoxazoles and secondary amines under metal-free conditions.
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