One-Pot Benzo[b]phosphole Synthesis through Sequential Alkyne Arylmagnesiation, Electrophilic Trapping, and Intramolecular Phospha-Friedel-Crafts Cyclization

Bin Wu, Rena Chopra, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

A one-pot multicomponent synthesis of a benzo[b]phosphole derivative has been achieved by a sequence of transition-metal-catalyzed arylmagnesiation of an internal alkyne, electrophilic trapping of the resulting alkenylmagnesium species with a dichloroorganophosphine, and an intramolecular phospha-Friedel-Crafts reaction. With appropriate arylmagnesiation and P-C bond formation conditions, the present method allows for the modular and expedient preparation of benzophospholes bearing a variety of substituents on the phosphorus atom, the C2 and C3 atoms, and the benzo moiety.

Original languageEnglish
Pages (from-to)5666-5669
Number of pages4
JournalOrganic letters
Volume17
Issue number22
DOIs
Publication statusPublished - 2015 Nov 20
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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