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铜催化环丙烯/重氮化合物与溴二氟乙酰胺的[3 + 1]环化反应:α,α-二氟-β-内酰胺衍生物的简便合成

Copper-catalyzed [3 + 1] cyclization of cyclopropenes/diazo compounds and bromodifluoroacetamides: facile synthesis of α,α-difluoro-β-lactam derivatives.

作者信息

Zhang Mengru, Li Hexin, Zhao Jinbo, Li Yan, Zhang Qian

机构信息

Department of Chemistry, Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Northeast Normal University Changchun 130024 China

Department of Chemistry, Jilin Provincial Key Laboratory of Carbon Fiber Development and Application, College of Chemistry and Life Science, Changchun University of Technology Changchun 130012 China.

出版信息

Chem Sci. 2021 Jul 29;12(35):11805-11809. doi: 10.1039/d1sc02930d. eCollection 2021 Sep 15.

Abstract

We have developed a novel copper-catalyzed cyclization of cyclopropenes/diazo compounds and bromodifluoroacetamides, efficiently synthesizing a series of α,α-difluoro-β-lactams in moderate to excellent yields under mild reaction conditions. This reaction represents the first example of [3 + 1] cyclization for the synthesis of β-lactams utilizing a metal carbene intermediate as the C1 synthon.

摘要

我们开发了一种新型的铜催化环丙烯/重氮化合物与溴二氟乙酰胺的环化反应,在温和的反应条件下以中等至优异的产率高效合成了一系列α,α-二氟-β-内酰胺。该反应代表了利用金属卡宾中间体作为C1合成子进行β-内酰胺合成的[3 + 1]环化反应的首例。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4a5/8442724/8cbec3a5d903/d1sc02930d-s1.jpg

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