4.4 Article

A simple and convenient synthesis of 2-(perfluoroalkyl)-4H-chromenes from salicyl N-tosylimines or salicylaldehydes and methyl 2-perfluoroalkynoates

Journal

TETRAHEDRON
Volume 65, Issue 45, Pages 9152-9156

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.09.030

Keywords

2-(Perfluoroalkyl)-4H-chromene; Salicyl N-tosylimine; Salicylaldehyde; Methyl 2-perfluoroalkynoate; Regioselectivity

Funding

  1. National Natural Science Foundation of China [20872088]
  2. Shanghai Municipal Education Commission [08ZZ44, J50102]

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Et3N-catalyzed reactions of salicyl N-tosylimines or salicylaldehydes with methyl 2-perfluoroalkynoates proceed smoothly at room temperature in dichloromethane (DCM) or dimethyl sulfoxide (DMSO) to give the corresponding fluorinated chromenes in good to excellent yields with high regioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

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