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Updated: Sep 30, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Merging strain-release and copper catalysis: the selective ring-opening cross-coupling of 1,2-oxazetidines with
Ji-Hang Xu1, Zi-Kui Liu1, Yan-Liu Tang1
1Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education & Hubei Key Laboratory of Catalysis and Materials Science, School of Chemistry and Materials Science, South-Central University for Nationalities, Wuhan 430074, China. huxiaoqiang@mail.scuec.edu.cn.
Abstract:
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.
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