PtBr2-catalyzed transformation of allyl(o-ethynylaryl)carbinol derivatives into functionalized indenes. Formal sp3 C-H bond activation

Gan B. Bajracharya, Nirmal K. Pahadi, Ilya D. Gridnev, Yoshinori Yamamoto

Research output: Contribution to journalArticle

91 Citations (Scopus)

Abstract

The PtBr2-catalyzed reaction of 1-ethynyl-2-(1-alkoxybut-3-enyl) benzenes at 120 °C in CH3CN gave functionalized indenes in good to allowable yields. Most probably, the hydrogen at the terminal alkyne is transferred to the adjacent internal β-carbon to form an (η2-vinylidene)platinum carbene intermediate, which activates the sp3 C-H bond at the benzylic carbon. This reaction pathway is supported by DFT calculations which suggest that the formation of the Pt-vinylidene complex is the rate-limiting stage for the whole transformation.

Original languageEnglish
Pages (from-to)6204-6210
Number of pages7
JournalJournal of Organic Chemistry
Volume71
Issue number16
DOIs
Publication statusPublished - 2006 Aug 1

ASJC Scopus subject areas

  • Organic Chemistry

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