Synlett 2015; 26(03): 340-344
DOI: 10.1055/s-0034-1379247
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© Georg Thieme Verlag Stuttgart · New York

Cobalt-Catalyzed Directed Alkylation of Olefinic C–H Bond with Primary and Secondary Alkyl Chlorides

Authors

  • Takeshi Yamakawa

    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore   Fax: +6567911961   Email: nyoshikai@ntu.edu.sg
  • Yuan Wah Seto

    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore   Fax: +6567911961   Email: nyoshikai@ntu.edu.sg
  • Naohiko Yoshikai*

    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore   Fax: +6567911961   Email: nyoshikai@ntu.edu.sg
Further Information

Publication History

Received: 28 August 2014

Accepted: 15 September 2014

Publication Date:
15 October 2014 (online)


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Abstract

A cobalt–N-heterocyclic carbene catalytic system promotes pyridine-directed olefinic C–H alkylation reactions using a variety of primary and secondary alkyl chlorides under mild conditions. Radical clock experiments suggest that the reaction involves single-electron transfer from the cobalt intermediate to the alkyl chloride.

Supporting Information