PtBr2-catalyzed consecutive enyne metathesis-aromatization of 1-(1-methoxy-but-3-enyl)-2-(1-alkynyl)benzenes: Dual role of the Pt catalyst

Gan B. Bajracharya, Itaru Nakamura, Yoshinori Yamamoto

Research output: Contribution to journalArticlepeer-review

63 Citations (Scopus)

Abstract

(Chemical Equation Presented) 1,7-Enynes 1, connected through an aromatic ring and bearing a leaving methoxy group at the 4-position, underwent the PtBr2-catalyzed enyne metathesis followed by aromatization in one pot to afford vinyl naphthalenes 3 in good to acceptable yields. The cyclobutene intermediate 11a and another intermediate 2a were isolated, indicating that PtBr2 acts as a dual role catalyst: (1) as a transition metal catalyst, it induces the enyne metathesis to produce 11a starting from 1a, and (2) as a Lewis acid catalyst, it facilitates elimination of MeOH from 2a to give the aromatized product 3a.

Original languageEnglish
Pages (from-to)892-897
Number of pages6
JournalJournal of Organic Chemistry
Volume70
Issue number3
DOIs
Publication statusPublished - 2005 Feb 4

ASJC Scopus subject areas

  • Organic Chemistry

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