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Catalytic Functionalization of C(sp2)H and C(sp3)H Bonds by Using Bidentate Directing Groups

Angewandte Chemie (International ed.), 2013-11, Vol.52 (45), p.11726-11743 [Peer Reviewed Journal]

Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim ;Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. ;ISSN: 1433-7851 ;EISSN: 1521-3773 ;DOI: 10.1002/anie.201301451 ;PMID: 24105797 ;CODEN: ACIEAY

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  • Title:
    Catalytic Functionalization of C(sp2)H and C(sp3)H Bonds by Using Bidentate Directing Groups
  • Author: Rouquet, Guy ; Chatani, Naoto
  • Subjects: Activation ; auxiliaries ; bidentate ligands ; Catalysis ; Catalysts ; CH functionalization ; directing groups ; Functional groups ; Organic compounds ; Proximity ; Strategy ; Transformations ; transition-metal catalysis
  • Is Part Of: Angewandte Chemie (International ed.), 2013-11, Vol.52 (45), p.11726-11743
  • Description: CH bonds are ubiquitous in organic compounds. It would, therefore, appear that direct functionalization of substrates by activation of CH bonds would eliminate the multiple steps and limitations associated with the preparation of functionalized starting materials. Regioselectivity is an important issue because organic molecules can contain a wide variety of CH bonds. The use of a directing group can largely overcome the issue of regiocontrol by allowing the catalyst to come into proximity with the targeted CH bonds. A wide variety of functional groups have been evaluated for use as directing groups in the transformation of CH bonds. In 2005, Daugulis reported the arylation of unactivated C(sp3)H bonds by using 8‐aminoquinoline and picolinamide as bidentate directing groups, with Pd(OAc)2 as the catalyst. Encouraged by these promising results, a number of transformations of CH bonds have since been developed by using systems based on bidentate directing groups. In this Review, recent advances in this area are discussed. Caught in the act: The regiochemical functionalization of CH bonds is a reliable strategy in synthetic chemistry. The regiocontrol can be achieved by using a directing group in the substrate which brings the catalyst into proximity with the target CH bond. Bidentate directing groups in particular have proven to be extremely effective.
  • Publisher: Weinheim: WILEY-VCH Verlag
  • Language: English
  • Identifier: ISSN: 1433-7851
    EISSN: 1521-3773
    DOI: 10.1002/anie.201301451
    PMID: 24105797
    CODEN: ACIEAY
  • Source: Alma/SFX Local Collection
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