Cu(OTf)2-catalyzed Beckmann Rearrangement of Ketones Using Hydroxylamine -O- sulfonic Acid (HOSA)

Synthesis (Stuttg). 2019 Oct;51(19):3709-3714. doi: 10.1055/s-0039-1690005.

Abstract

The Beckmann Rearrangement (BKR) of ketones to secondary amides often requires harsh reaction conditions that limit its practicality and scope. Herein, we describe the Cu(OTf)2-catalyzed BKR of ketones under mild reaction conditions using hydroxylamine-O-sulfonic acid (HOSA), a commercial water soluble aminating agent. This method is compatible with most functional groups and directly provides the desired amides in good to excellent yields.

Keywords: Beckmann Rearrangement; Cu(OTf)2; Hydroxylamine-O-sulfonic acid (HOSA); Ketone; Secondary amide.