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      Copper-boryl mediated organic synthesis

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          Abstract

          The diverse applications of copper-catalyzed borylation, which has become an essential strategy in modern synthetic organic chemistry, are reviewed and illustrated.

          Abstract

          Organoboron compounds are valuable synthetic intermediates that find application in a diverse variety of processes including both C–X and C–C bond-forming transformations. This has been achieved by using a variety of boron derivatives. Of these, boronate esters are probably the most versatile and, reflecting this, methods for the generation of boronate esters are of considerable current interest. Given the mild reaction conditions, good functional group tolerance, and low cost of the metal catalyst, the use of copper-boryl reagents is particularly attractive. In this review, methodologies in copper-boryl chemistry are discussed and the many different transformations possible are surveyed.

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          C-H activation for the construction of C-B bonds.

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            Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse.

            Although known for over 90 years, only in the past two decades has the chemistry of diboron(4) compounds been extensively explored. Many interesting structural features and reaction patterns have emerged, and more importantly, these compounds now feature prominently in both metal-catalyzed and metal-free methodologies for the formation of B-C bonds and other processes.
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              Alkylboronic Esters from Copper-Catalyzed Borylation of Primary and Secondary Alkyl Halides and Pseudohalides

              Easy access: An unprecedented copper-catalyzed cross-coupling reaction of the title compounds with diboron reagents is described (see scheme; Ts = 4-toluenesulfonyl). This reaction can be used to prepare both primary and secondary alkylboronic esters having diverse structures and functional groups. The resulting products would be difficult to access by other means.
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                Author and article information

                Contributors
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                Journal
                CSRVBR
                Chemical Society Reviews
                Chem. Soc. Rev.
                Royal Society of Chemistry (RSC)
                0306-0012
                1460-4744
                2018
                2018
                : 47
                : 19
                : 7477-7494
                Affiliations
                [1 ]Department of Chemistry
                [2 ]University of Durham
                [3 ]Science Laboratories South Road
                [4 ]Durham DH1 3LE
                [5 ]UK
                [6 ]Virginia Tech
                [7 ]Blacksburg
                [8 ]USA
                [9 ]Department of Chemistry and Biochemistry
                [10 ]Mount Allison University
                [11 ]Sackville
                [12 ]Canada
                Article
                10.1039/C7CS00816C
                30206614
                27d943af-db35-4213-8a23-85efc413bb73
                © 2018

                http://creativecommons.org/licenses/by/3.0/

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