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Open Access Transition-metal-free Oxidative Coupling Reactions for the Formation of C–C and C–N Bonds Mediated by TEMPO and its Derivatives

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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 Münster. 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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Keywords: 2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXYL RADICAL (TEMPO); CH-AMINATION; N-OXOAMMONIUM SALTS; OXIDATIVE COUPLING; TRANSITION-METAL-FREE

Document Type: Research Article

Affiliations: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, D-48149 Münster, Germany

Publication date: June 1, 2012

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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