Merging strain-release and copper catalysis: the selective ring-opening cross-coupling of 1,2-oxazetidines with boronic acids.
Ji-Hang XuZi-Kui LiuYan-Liu TangYang GaoXiao-Qiang HuPublished in: Chemical communications (Cambridge, England) (2022)
An unprecedented ring-opening cross-coupling of 1,2-oxazetidines with readily available arylboronic acids is achieved for the first time by copper catalysis. Unlike the known electrophilic oxygen reactivity in coupling with organometallic reagents, 1,2-oxazetidines were utilized as formaldimine precursors in this protocol. Remarkable features of this reaction include simple operation, inexpensive catalyst, broad scope and high regioselectivity, delivering a wide array of aminomethylation products. The practicality of this reaction was validated in the one-step downstream transformation of the obtained products into synthetically important molecules and late-stage modification of bioactive acids.