Multicomponent type II anion relay chemistry (ARC): One-pot syntheses of 2,3-disubstituted furans and thiophenes

Nelmi O. Devarie-Baez, Won Suk Kim, Amos B. Smith, Ming Xian

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

Effective, one-pot syntheses of 2,3-disubstituted furans and thiophenes, exploiting 2-fert-butyldimethylsilyl-3-formylfuran and -thiophene as the respective Afunctional linchpins, have been developed. The synthetic protocol involves multicomponent type II Anion Relay Chemistry (ARC) mediated by a solvent-controlled C(sp 2)→0 1,4-Brook rearrangement. Simple organolithiums and α-disubstituted ester enolates prove effective as the initiating nucleophiles.

Original languageEnglish
Pages (from-to)1861-1864
Number of pages4
JournalOrganic Letters
Volume11
Issue number8
DOIs
StatePublished - 16 Apr 2009

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