Nickel-catalyzed cross-electrophile C-Ge coupling of benzyl pivalates and chlorogermanes

The C-Ge cross-coupling offers a promising approach for the precise synthesis of organogermanes. However, the current methods are primarily effective in the germylation of organo(pseudo)halides. This work demonstrates the possibility of transferring low-cost and easily available ester groups into organogermanes through the cleavage of stable C-O bonds. Primary, secondary, and even tertiary benzylic pivalates were coupled well with chlorogermanes. The reactions proceed under mild conditions. The scalability of this reaction and derivatization of the formed benzylgermanes are demonstrated.

Automated summary

The C-Ge cross-coupling is a promising method for the precise synthesis of organogermanes. This study demonstrates the possibility of converting low-cost and easily available ester groups into organogermanes through cleavage of stable C-O bonds. The coupling of primary, secondary, and even tertiary benzylic pivalates with chlorogermanes is achieved under mild conditions. The scalability of the reaction and the derivatization of the formed benzylgermanes are also demonstrated.