4.4 Article

One-pot solvent-free synthesis of triaryl- and triheteroarylmethanes by Bi(OTf)3-catalyzed Friedel-Crafts reaction of arenes/heteroarenes with trialkyl orthoformates

Journal

TETRAHEDRON
Volume 74, Issue 33, Pages 4373-4380

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.05.079

Keywords

Triarylmethane; Triheteroarylmethane; Bismuth(III) triflate; Friedel-Crafts reaction; Trialkyl orthoformate

Funding

  1. Burapha University through the National Research Council of Thailand [20/2556, 60/2557]
  2. Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commission on Higher Education, Ministry of Education of Thailand

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A convenient, practical and highly efficient one-pot method has been developed for the synthesis of triaryl- and triheteroarylmethane derivatives by Bi(OTf)(3)-catalyzed Friedel-Crafts alkylation of trialkyl orthoformates in combination with a wide variety of arenes/heteroarenes at room temperature under solvent-free conditions and in an air atmosphere. The methodology offers an operational simplicity, high atom economy and environmentally benign procedure. Furthermore, selected compound 3k showed promising anti-inflammatory activity with inhibition nitric oxide and did not exhibit significant cytotoxic effects on macrophage cells. (C) 2018 Published by Elsevier Ltd.

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