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

• Main Authors: Laskar, Roshayed Ali, Ding, Wei, Yoshikai, Naohiko
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2022
• Subjects: Science::Chemistry; Benziodoxole Triflate; Unsaturated Ketones
• Online Access: https://hdl.handle.net/10356/160362
• Institution: Nanyang Technological University

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-λ3-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-λ3-iodanylenones can be utilized for facile Pd-catalyzed cross-coupling for the synthesis of multisubstituted enones.