4.8 Article

Rhodium-Catalyzed Cyanation of C(sp2)-H Bond of Alkenes

Journal

ORGANIC LETTERS
Volume 17, Issue 15, Pages 3766-3769

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b01746

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Funding

  1. Indian Institute of Technology Madras New Faculty Scheme
  2. Board of Research in Nuclear Sciences (ERNS) through the DAE Young Scientist Award [2012/20/37C/14/BRNS]
  3. Council of Scientific & Industrial Research (CSIR)

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Efficient and selective rhodium-catalyzed cyanation of chelation-assisted C-H bonds of alkenes has been accomplished using environmentally benign N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as a cyanating reagent. The developed methodology tolerates various functional groups and allows the synthesis of diverse substituted acrylonitriles in good to excellent yields. Furthermore, the potential of the methodology was demonstrated through the formal synthesis of chlorpheniramine-based antagonist.

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