An efficient method for the production of terminal alkynes from 1,1-dibromo-1-alkenes and its application in the total synthesis of natural product dihydroxerulin

Shihui Liu, Xiaobei Chen, Yanwei Hu, Laiqi Yuan, Shaohua Chen, Ping Wu, Wei Wang, Shilei Zhang, Wei Zhang

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

An efficient method of preparing various terminal alkynes from 1,1-dibromo-1-alkenes by using TBAF (tetra-n-butylammonium fluoride) as a base and triphenylphosphane as a reductant was developed. This method is strong base and low/high temperatures free, and can tolerate a broad range of substrates. These advantages were well demonstrated by the application of this method to the total synthesis of polyene natural product dihydroxerulin.

Original languageEnglish (US)
Pages (from-to)553-560
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume357
Issue number2-3
DOIs
StatePublished - Feb 9 2015
Externally publishedYes

Keywords

  • 1,1-dibromo-1-alkenes
  • Dihydroxerulin
  • Terminal alkynes
  • Tetra-n-butylammonium fluoride
  • Triphenylphosphane

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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