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钯催化串联酯舞蹈/脱羰偶联反应。

Palladium-Catalyzed Tandem Ester Dance/Decarbonylative Coupling Reactions.

机构信息

Department of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo 162-0041, Japan.

出版信息

Org Lett. 2022 Jun 3;24(21):3855-3860. doi: 10.1021/acs.orglett.2c01432. Epub 2022 May 23.

Abstract

"Dance reaction" on the aromatic ring is a powerful method in organic chemistry to translocate functional groups on arene scaffolds. Notably, dance reactions of halides and pseudohalides offer a unique platform for the divergent synthesis of substituted (hetero)aromatic compounds when combined with transition-metal-catalyzed coupling reactions. Herein, we report a tandem reaction of ester dance and decarbonylative coupling enabled by palladium catalysis. In this reaction, 1,2-translocation of the ester moiety on the aromatic ring is followed by decarbonylative coupling with nucleophiles to enable the installation of a variety of nucleophiles at the position adjacent to the ester in the starting material.

摘要

“芳环上的舞蹈反应”是有机化学中一种强大的方法,可以将官能团迁移到芳烃支架上。值得注意的是,当与过渡金属催化偶联反应结合使用时,卤化物和拟卤化物的舞蹈反应为取代(杂)芳烃化合物的发散合成提供了独特的平台。在此,我们报告了通过钯催化实现的酯舞蹈和脱羰偶联的串联反应。在该反应中,芳环上酯基的 1,2-迁移,随后与亲核试剂发生脱羰偶联,使各种亲核试剂能够安装在起始原料中酯基相邻的位置上。

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