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      Functionalization of C(sp3)-H bonds using a transient directing group

      Author(s): , , , ,
      Publication date Created:
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      Journal: Science
      Publisher: American Association for the Advancement of Science (AAAS)

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

          Xiao Chen, Keary M Engle, Dong-Hui Wang … (2009)
          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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            Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.

            Denise A Colby, Robert Bergman, Jonathan Ellman (2010)
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              Towards mild metal-catalyzed C-H bond activation.

              Joanna Wencel-Delord, Thomas Dröge, Fan Liu … (2011)
              Functionalizing traditionally inert carbon-hydrogen bonds represents a powerful transformation in organic synthesis, providing new entries to valuable structural motifs and improving the overall synthetic efficiency. C-H bond activation, however, often necessitates harsh reaction conditions that result in functional group incompatibilities and limited substrate scope. An understanding of the reaction mechanism and rational design of experimental conditions have led to significant improvement in both selectivity and applicability. This critical review summarizes and discusses endeavours towards the development of mild C-H activation methods and wishes to trigger more research towards this goal. In addition, we examine select examples in complex natural product synthesis to demonstrate the synthetic utility of mild C-H functionalization (84 references). This journal is © The Royal Society of Chemistry 2011
              Article 0 comments Cited 572 times – based on 0 reviews     Review now
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                Author and article information

                Journal
                Title: Science
                Abbreviated Title: Science
                Publisher: American Association for the Advancement of Science (AAAS)
                ISSN (Print): 0036-8075
                ISSN (Electronic): 1095-9203
                Publication date Created: January 14 2016
                Publication date (Print): January 14 2016
                Volume: 351
                Issue: 6270
                Pages: 252-256
                Article
                DOI: 10.1126/science.aad7893
                PMC ID: 4817545
                PubMed ID: 26816374
                SO-VID: 1afcb172-478c-4735-ab5e-5010d1dfd5c9
                Copyright © © 2016
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                http://www.sciencemag.org/about/science-licenses-journal-article-reuse

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