4.4 Article

An efficient synthesis of 5-substituted 1H-tetrazoles via B(C6F5)3 catalyzed [3+2] cycloaddition of nitriles and sodium azide

Journal

TETRAHEDRON LETTERS
Volume 55, Issue 24, Pages 3507-3510

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.04.089

Keywords

5-Substituted 1H-tetrazole; Trispentafluorophenyl borane [B(C6F5)(3)]; Nontoxic; NaN3; [3+2] Cycloaddition

Funding

  1. Department of Pharmaceuticals (Ministry of Chemicals and Fertilizers)

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A simple and efficient protocol is developed for the synthesis of 5-substituted 1H-tetrazole derivatives from various nitriles and sodium azide (NaN3) via [3+2] cycloaddition reaction using B(C6F5)(3) as a catalyst. The present synthetic method displayed significant advantages such as low catalyst loading, mild reaction conditions, low toxicity, easy work-up, high yields, and compatibility with other functional groups. (C) 2014 Elsevier Ltd. All rights reserved.

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