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-λ<sup>3</sup>-iodanyl 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-λ<sup>3</sup>-iodanylenones can be utilized for facile Pd-catalyzed cross-coupling for the synthesis of multisubstituted enones.

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

ACS Spring Meeting 2021

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