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.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry