Synthesis of Hindered Biaryls via Aryne Addition and in Situ Dimerization

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

ORGANIC LETTERS, cilt.17, sa.11, ss.2649-2651, 2015 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 17 Sayı: 11
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1021/acs.orglett.5b01115
  • Dergi Adı: ORGANIC LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2649-2651
  • Bursa Uludağ Üniversitesi Adresli: Evet

Özet

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.