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Nickel‐Catalyzed Reductive C−Ge Coupling of Aryl/Alkenyl Electrophiles with Chlorogermanes

Pei‐Feng Su, Ke Wang, Xuejing Peng, Xiaobo Pang, Peng Guo, Xing‐Zhong Shu

2021Angewandte Chemie International Edition80 citationsDOI

Abstract

Abstract Cross‐electrophile coupling has emerged as a promising tool for molecular synthesis; however, current studies have focused mainly on forging C−C bonds. We report a cross‐electrophile C−Ge coupling reaction and thereby demonstrate the possibility of constructing organogermanes from carbon electrophiles and chlorogermanes. The reaction proceeds under mild conditions and offers access to both aryl and alkenyl germanes. Electron‐rich, electron‐poor, and ortho ‐/ meta ‐/ para ‐substituted (hetero)aryl electrophiles, as well as cyclic and acyclic alkenyl electrophiles, were coupled. Gram‐scale reaction, incorporation of the ‐GeR 3 moiety into complex biologically active molecules, and derivatization of formed organogermanes are demonstrated.

Topics & Concepts

ElectrophileArylMoietyChemistryCoupling reactionCatalysisCombinatorial chemistryDerivatizationMedicinal chemistryOrganic chemistryAlkylHigh-performance liquid chromatographyCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistryCatalytic C–H Functionalization Methods
Nickel‐Catalyzed Reductive C−Ge Coupling of Aryl/Alkenyl Electrophiles with Chlorogermanes | Litcius