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

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 -GeR₃ moiety into complex biologically active molecules, and derivatization of formed organogermanes are demonstrated.

Keywords: germylation; nickel; organogermanes; synthetic methods.