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C−H Cyanation of 6‐Ring N‐Containing Heteroaromatics

Elbert, Bryony L. ; Farley, Alistair J. M. ; Gorman, Timothy W. ; Johnson, Tarn C. ; Genicot, Christophe ; Lallemand, Bénédicte ; Pasau, Patrick ; Flasz, Jakub ; Castro, José L. ; Maccoss, Malcolm ; Paton, Robert S. ; Schofield, Christopher J. ; Smith, Martin D. ; Willis, Michael C. ; Dixon, Darren J.

Chemistry – A European Journal, 20 October 2017, Vol.23(59), pp.14733-14737 [Peer Reviewed Journal]

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  • Title:
    C−H Cyanation of 6‐Ring N‐Containing Heteroaromatics
  • Author: Elbert, Bryony L. ; Farley, Alistair J. M. ; Gorman, Timothy W. ; Johnson, Tarn C. ; Genicot, Christophe ; Lallemand, Bénédicte ; Pasau, Patrick ; Flasz, Jakub ; Castro, José L. ; Maccoss, Malcolm ; Paton, Robert S. ; Schofield, Christopher J. ; Smith, Martin D. ; Willis, Michael C. ; Dixon, Darren J.
  • Description: Heteroaromatic nitriles are important compounds in drug discovery, both for their prevalence in the clinic and due to the diverse range of transformations they can undergo. As such, efficient and reliable methods to access them have the potential for far‐reaching impact across synthetic chemistry and the biomedical sciences. Herein, we report an approach to heteroaromatic C−H cyanation through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoromethanesulfinate to regenerate the cyanated heteroaromatic ring. This one‐pot protocol is simple to perform, is applicable to a broad range of decorated 6‐ring N‐containing heterocycles, and has been shown to be suitable for late‐stage functionalization of complex drug‐like architectures. N‐heteroaromatic C−H cyanation procedure by triflic anhydride N‐activation, nucleophilic addition of cyanide, and concomitant elimination of trifluoromethanesulfinate is reported. The protocol is simple to perform, has computationally predictable site selectivity, and is applicable to a broad range of decorated 6‐ring N‐containing heterocycles, including complex drug‐like architectures.
  • Is Part Of: Chemistry – A European Journal, 20 October 2017, Vol.23(59), pp.14733-14737
  • Identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201703931
  • Subjects: Cyanation ; Heterocycles ; Late-Stage Functionalization ; Nitriles
  • Language: English

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