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Palladium(II)-Catalyzed Allylic CH Oxidation of Hindered Substrates Featuring Tunable Selectivity Over Extent of Oxidation

Angewandte Chemie (International ed.), 2015-09, Vol.54 (38), p.11186 [Peer Reviewed Journal]

2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ;ISSN: 1433-7851 ;EISSN: 1521-3773 ;DOI: 10.1002/anie.201504007 ;CODEN: ACIEAY

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  • Title:
    Palladium(II)-Catalyzed Allylic CH Oxidation of Hindered Substrates Featuring Tunable Selectivity Over Extent of Oxidation
  • Author: Xing, Xiangyou ; O'Connor, Nicholas R ; Stoltz, Brian M
  • Subjects: Oxidation
  • Is Part Of: Angewandte Chemie (International ed.), 2015-09, Vol.54 (38), p.11186
  • Description: The use of Oxone and a palladium(II) catalyst enables the efficient allylic CH oxidation of sterically hindered [alpha]-quaternary lactams which are unreactive under known conditions for similar transformations. This simple, safe, and effective system for CH activation allows for unusual tunable selectivity between a two-electron oxidation to the allylic acetates and a four-electron oxidation to the corresponding enals, with the dominant product depending on the presence or absence of water. The versatile synthetic utility of both the allylic acetate and enal products accessible through this methodology is also demonstrated.
  • Publisher: Weinheim: Wiley Subscription Services, Inc
  • Language: English
  • Identifier: ISSN: 1433-7851
    EISSN: 1521-3773
    DOI: 10.1002/anie.201504007
    CODEN: ACIEAY
  • Source: Alma/SFX Local Collection
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