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      C-H activation: a complementary tool in the total synthesis of complex natural products.

      Chemistry (Weinheim an Der Bergstrasse, Germany)

      Wiley

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          Abstract

          The recent advent of transition-metal mediated C-H activation is revolutionizing the synthetic field and gradually infusing a "C-H activation mind-set" in both students and practitioners of organic synthesis. As a powerful testament of this emerging synthetic tool, applications of C-H activation in the context of total synthesis of complex natural products are beginning to blossom. Herein, recently completed total syntheses showcasing creative and ingenious incorporation of C-H activation as a strategic manoeuver are compared with their "non-C-H activation" counterparts, illuminating a new paradigm in strategic synthetic design.

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          Most cited references 332

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          Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

          In the past decade, palladium-catalyzed C-H activation/C-C bond-forming reactions have emerged as promising new catalytic transformations; however, development in this field is still at an early stage compared to the state of the art in cross-coupling reactions using aryl and alkyl halides. This Review begins with a brief introduction of four extensively investigated modes of catalysis for forming C-C bonds from C-H bonds: Pd(II)/Pd(0), Pd(II)/Pd(IV), Pd(0)/Pd(II)/Pd(IV), and Pd(0)/Pd(II) catalysis. A more detailed discussion is then directed towards the recent development of palladium(II)-catalyzed coupling of C-H bonds with organometallic reagents through a Pd(II)/Pd(0) catalytic cycle. Despite the progress made to date, improving the versatility and practicality of this new reaction remains a tremendous challenge.
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            Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds.

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              Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.

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                Author and article information

                Journal
                10.1002/chem.201201329
                22736530

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