4.7 Article

TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes: A novel method for the solid-phase synthesis of dihydrocoumarins and coumarins

Journal

CHINESE CHEMICAL LETTERS
Volume 23, Issue 6, Pages 631-634

Publisher

ELSEVIER SCIENCE INC
DOI: 10.1016/j.cclet.2012.03.022

Keywords

Lewis acid; Seleno-arylation; Succinimidyl selenide; Solid-phase synthesis; Dihydrocoumarins; Coumarins

Funding

  1. National Natural Science Foundation of China [20802063, 21162032]
  2. Foundation of the Key Laboratory of Medicinal Chemistry of Natural Resource (Yunnan University), Ministry of Education, China

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TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocoumarins possessing a seleno-functionality, followed by traceless cleavage of selenium linker to provide dihydrocoumarins and coumarins in good yields and purities. (C) 2012 E Tang. Published by Elsevier B.V on behalf of Chinese Chemical Society. All rights reserved.

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