Iodo(III)-Meyer−Schuster rearrangement of propargylic alcohols promoted by benziodoxole triflate

Roshayed Ali Laskar, Wei Ding, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Benziodoxole triflate (BXT), a cyclic iodine(III) electrophile, has been found to promote a rearrangement of propargylic alcohols into α,β-unsaturated ketones bearing an α-λ3iodanyl group. This iodo(III)-Meyer−Schuster rearrangement proceeds under mild conditions and tolerates a variety of functionalized propargylic alcohols, thus complementing previously reported halogen-intercepted Meyer−Schuster rearrangement. The α-λ3-iodanylenones can be utilized for facile Pd-catalyzed cross-coupling for the synthesis of multisubstituted enones.

Original languageEnglish
Pages (from-to)1113-1117
Number of pages5
JournalOrganic letters
Volume23
Issue number3
DOIs
Publication statusPublished - 2021 Feb 5
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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