A 2:1 coupling reaction of arynes with aldehydes via o-quinone methides: straightforward synthesis of 9-arylxanthenes

Hiroto Yoshida; Masahiko Watanabe; Hiroyuki Fukushima; Joji Ohshita; Atsutaka Kunai

doi:10.1021/ol048298b

A 2:1 coupling reaction of arynes with aldehydes via o-quinone methides: straightforward synthesis of 9-arylxanthenes

Org Lett. 2004 Oct 28;6(22):4049-51. doi: 10.1021/ol048298b.

Authors

Hiroto Yoshida¹, Masahiko Watanabe, Hiroyuki Fukushima, Joji Ohshita, Atsutaka Kunai

Affiliation

¹ Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan. yhiroto@hiroshima-u.ac.jp

PMID: 15496096
DOI: 10.1021/ol048298b

Abstract

[reaction: see text] A novel coupling reaction, where an aldehyde and two molar amounts of an aryne are assembled selectively, has been demonstrated to afford diverse 9-arylxanthene derivatives in one step. o-Quinone methide arising from the [2 + 2] cycloaddition of an aldehyde with an aryne was postulated as a transient intermediate.