2,3-disubstituted benzofuran and indole by copper-mediated C-C bond extension reaction of 3-zinciobenzoheterole

Masaharu Nakamura; Laurean Ilies; Saika Otsubo; Eiichi Nakamura

doi:10.1021/ol060896y

2,3-disubstituted benzofuran and indole by copper-mediated C-C bond extension reaction of 3-zinciobenzoheterole

Org Lett. 2006 Jun 22;8(13):2803-5. doi: 10.1021/ol060896y.

Authors

Masaharu Nakamura¹, Laurean Ilies, Saika Otsubo, Eiichi Nakamura

Affiliation

¹ Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Japan. masaharu@scl.kyoto-u.ac.jp

PMID: 16774261
DOI: 10.1021/ol060896y

Abstract

[reaction: see text] A metalative 5-endo-dig cyclization reaction of 2-ynylphenoles or anilines effected by BuLi and ZnCl(2) produces 3-zinciobenzoheteroles in excellent yield. These intermediates have been transmetalated to the corresponding cuprates and allowed to react with electrophiles to produce a variety of 2,3-disubstituted benzofurans and indoles.