Diversity-Oriented Synthesis of Furo[3,2-c]coumarins and Benzofuranyl Chromenones through Chemoselective Acylation/Wittig Reaction

Shu Mei Yang, Chein Yi Wang, Chun Kai Lin, Praneeth Karanam, Ganapuram Madhusudhan Reddy, Yi Ling Tsai, Wenwei Lin

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A highly efficient and chemoselective one-pot protocol for the diversity-oriented synthesis of two types of coumarin-based formal cross-coupling adducts, furo[3,2-c]coumarins and 3-benzofuranyl chromenones, is described. Key attributes of the methodology are an initial chemoselective acylation of functionalized phosphorus zwitterions and a subsequent chemoselective intramolecular Wittig reaction that preferentially resulted in one of the two coumarin derivatives in high yield, depending on relative reactivities and the addition sequence of the acylating agents.

Original languageEnglish
Pages (from-to)1668-1672
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number6
DOIs
Publication statusPublished - 2018 Feb 5

Keywords

  • Wittig reactions
  • chemoselectivity
  • diversity-oriented synthesis
  • multicomponent reactions
  • organophosphonium salts

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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