Synthesis of Hindered Biaryls via Aryne Addition and in Situ Dimerization

Garcia-Lopez J., Cetin M. , Greaney M. F.

ORGANIC LETTERS, vol.17, no.11, pp.2649-2651, 2015 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 17 Issue: 11
  • Publication Date: 2015
  • Doi Number: 10.1021/acs.orglett.5b01115
  • Title of Journal : ORGANIC LETTERS
  • Page Numbers: pp.2649-2651


Benzynes generated under Knochel conditions from 2-iodophenylsulfonates and (PrMgCl)-Pr-i smoothly add to thiol, selenol, and amine nucleophiles. Treatment of the resulting aryl Grignard intermediate with a copper salt and an organic oxidant then affords symmetrical biaryls in good yield. 3-Substituted arynes undergo regioselective addition, enabling synthesis of atropisomeric biaryls with chelating S, Se, or N groups in the 2,2' positions.