Synthesis of hindered 1-arylnaphthalene derivatives via ring expansion of benzocyclobutenones

Toshiyuki Hamura; Makoto Miyamoto; Takashi Matsumoto; Keisuke Suzuki

doi:10.1021/ol016956b

Synthesis of hindered 1-arylnaphthalene derivatives via ring expansion of benzocyclobutenones

Org Lett. 2002 Jan 24;4(2):229-32. doi: 10.1021/ol016956b.

Authors

Toshiyuki Hamura¹, Makoto Miyamoto, Takashi Matsumoto, Keisuke Suzuki

Affiliation

¹ Department of Chemistry, Tokyo Institute of Technology, and CREST, Japan Science and Technology (JST) Corporation, O-okayama, Meguro-ku, Tokyo 152-8551, Japan.

PMID: 11796057
DOI: 10.1021/ol016956b

Abstract

[reaction: see text] Various 1-arylnaphthalenes, including highly substituted derivatives, are accessible via a simple two-step process. Treatment of alkenylbenzocyclobutenones with aryllithium provides two-carbon expanded dihydronaphthalenes, which are readily dehydrated by MsCl-Et(3)N or PPTS in MeOH.