Electrochemistry-Enabled C-Heteroatom Bond Formation of Alkyl Germanes
Markus D. Schoetz, Kristina Deckers, Gurdeep Singh, Eric Ahrweiler, Annika Hoeppner, Franziska Schoenebeck
Abstract
Because of their robustness and orthogonal reactivity features, alkyl germanes bear significant potential as functional handles for the construction of C(sp 3 )-rich scaffolds, especially in the context of modular synthetic approaches. However, to date, only radical-based reactivity has been accessible from these functional handles, which limits the types of possible decorations. Here, we describe the first general C(sp 3 )–heteroatom bond formation of alkyl germanes (−GeEt 3 ) by leveraging electrochemistry to unlock polar reactivity. This approach allowed us to couple C(sp 3 )–GeEt 3 with a variety of nucleophiles to construct ethers, esters, amines, amides, sulfonamides, sulfides, as well as C–P, C–F, and C–C bonds. The compatibility of the electrochemical approach with a modular synthetic strategy of a C 1 motif was also showcased, involving the sequential functionalization of Cl, Bpin, and ultimately GeEt 3 via electrochemistry.