4.4 Article

Friedel-Crafts cyclization of tertiary alcohols using bismuth(III) triflate

Journal

TETRAHEDRON LETTERS
Volume 54, Issue 32, Pages 4330-4332

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.06.026

Keywords

Friedel-Crafts cyclization; Bismuth(III) triflate; Heterocycles; Tertiary alcohols

Funding

  1. NSF [BIR-9512269]
  2. Oklahoma State Regents for Higher Education
  3. W.M. Keck Foundation
  4. Conoco, Inc.
  5. OSU College of Arts and Sciences

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Bismuth(III) triflate [Bi(OTf)(3)] has been developed as an efficient and mild catalyst for intramolecular Friedel-Crafts cyclizations of tertiary alcohols to prepare disubstituted tetrahydronapthalenes, chromans, thiochromans, tetrahydroquinolines, and tetrahydroiso-quinolines. The method represents a unified strategy to synthesize a variety of ring systems from tertiary alcohols using a common Lewis acid. (C) 2013 Elsevier Ltd. All rights reserved.

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