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用于重氮辛环官能化的施蒂勒-铃木交叉偶联反应

Stille Suzuki - cross-coupling for the functionalization of diazocines.

作者信息

Walther Melanie, Kipke Waldemar, Renken Raul, Staubitz Anne

机构信息

University of Bremen, Institute for Analytical and Organic Chemistry Leobener Straße 7 D-28359 Bremen Germany

University of Bremen, MAPEX Center for Materials and Processes Bibliothekstraße 1 D-28359 Bremen Germany.

出版信息

RSC Adv. 2023 May 30;13(23):15805-15809. doi: 10.1039/d3ra02988c. eCollection 2023 May 22.

Abstract

Diazocines are azobenzene derived macrocyclic photoswitches with well resolved photostationary states for the ()- and ()-isomers, which improves their addressability by light. In this work, effective procedures for the stannylation and borylation of diazocines in different positions are reported. Their use in Stille cross-coupling and Suzuki cross-coupling reactions with organic bromides is demonstrated in yields of 47-94% (Stille cross-coupling) and 0-95% (Suzuki cross-coupling), respectively.

摘要

重氮辛是一种由偶氮苯衍生的大环光开关,其()-异构体和()-异构体具有良好分辨的光稳态,这提高了它们通过光进行寻址的能力。在这项工作中,报道了在不同位置对重氮辛进行锡基化和硼基化的有效方法。分别以47-94%(Stille交叉偶联)和0-95%(Suzuki交叉偶联)的产率证明了它们在与有机溴化物的Stille交叉偶联反应和Suzuki交叉偶联反应中的应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0443/10227463/c64dbcbd59c2/d3ra02988c-s1.jpg

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