Directing group-controlled hydrosilylation: Regioselective functionalization of alkyne

Yuuya Kawasaki, Youhei Ishikawa, Kazunobu Igawa, Katsuhiko Tomooka

Research output: Contribution to journalArticle

62 Citations (Scopus)

Abstract

Pt(0)-catalyzed hydrosilylation of unsymmetric alkynes proceeds in a highly regioselective manner with a dimethylvinylsilyl (DMVS) group as the directing group. This hydrosilylation affords a single regioisomer of silylalkenes from propargylic and homopropargylic alcohol derivatives. DMVS also has an accelerating effect that allows group-selective hydrosilylation of the DMVS-attached alkyne prior to that of other alkynes. Combined hydrosilylation and transformation reactions of the resulting silylalkenes afford various tri-substituted alkenes and multi-oxy-functionalized compounds with high regioselectivity from unsymmetric alkynes.

Original languageEnglish
Pages (from-to)20712-20715
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number51
DOIs
Publication statusPublished - Dec 28 2011

    Fingerprint

All Science Journal Classification (ASJC) codes

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

Cite this