Lanthanide triflate-catalyzed preparation of beta,beta-difluorohomopropargyl alcohols in aqueous media. Application to the synthesis of 4,4-difluoroisochromans

Satoru Arimitsu; Gerald B Hammond

doi:10.1021/jo0614588

Lanthanide triflate-catalyzed preparation of beta,beta-difluorohomopropargyl alcohols in aqueous media. Application to the synthesis of 4,4-difluoroisochromans

J Org Chem. 2006 Oct 27;71(22):8665-8. doi: 10.1021/jo0614588.

Authors

Satoru Arimitsu¹, Gerald B Hammond

Affiliation

¹ Department of Chemistry, University of Louisville, Louisville, Kentucky, 40292, USA.

PMID: 17064055
DOI: 10.1021/jo0614588

Abstract

An indium-mediated Barbier-type reaction of difluoropropargyl bromide with several aldehydes in aqueous media was enhanced by a catalytic amount of a lanthanide triflate (5 mol %). The reaction gave the corresponding beta,beta-difluorohomopropargyl alcohols with high regioselectivity. The [2 + 2 + 2] alkyne cyclotrimerization of beta,beta-difluorohomopropargyl alcohols with monosubstituted acetylenes produced 4,4-difluoroisochromans in good yields with moderate regioselectivity.