Rhenium-catalyzed anti -Markovnikov addition reaction of methanetricarboxylates to unactivated terminal acetylenes

Shunsuke Hori, Masahito Murai, Kazuhiko Takai

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

A novel anti-Markovnikov addition reaction of methanetricarboxylates with terminal acetylenes under neutral conditions was achieved using a rhenium complex. This transformation represents a rare example of intermolecular anti-Markovnikov addition of carbon nucleophiles to unactivated terminal acetylenes. 1,3-Diesters having bulky substituents at the active methylene carbon are also applicable as substrates to provide anti-Markovnikov adducts as single regio- and stereoisomers. Preliminary mechanistic studies imply that the rhenium vinylidene species is the key intermediate in the current catalytic cycle.

Original languageEnglish
Pages (from-to)1452-1457
Number of pages6
JournalJournal of the American Chemical Society
Volume137
Issue number4
DOIs
Publication statusPublished - Feb 4 2015

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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