Harnessing Supported Gold Nanoparticle as a Single-Electron Transfer Catalyst for Decarboxylative Cross-Coupling

We found that gold nanoparticles function as single-electron transfer catalysts to promote decarboxylative cross-coupling between N-hydroxy phthalimide esters and disilanes or diborons. A variety of disilanes coupled with alkyl radicals could be generated from N-hydroxy phthalimide esters via single-electron reduction by active carbon-supported gold nanoparticle catalysts to afford diverse alkylsilanes without the need for external bases. Furthermore, the present gold catalytic system was also effective for decarboxylative carbon-boron coupling to afford alkyl boronates. A detailed mechanistic investigation revealed that single-electron transfer mediated by supported gold nanoparticles enabled the generation of alkyl radical and silyl radical, thereby enabling radical cross-coupling. The reusability and environmentally-friendly nature of supported gold catalyst as well as the scalability of the reaction system enable the practical transformation of carboxylic acid derivatives into value-added organosilicon and organoboron compounds.

Automated summary

We discovered that gold nanoparticles act as catalysts for the single-electron transfer in the decarboxylative cross-coupling reaction between N-hydroxy phthalimide esters and disilanes or diborons. This allows for the generation of various alkylsilanes and alkyl boronates without the need for external bases. Mechanistic investigation revealed that the supported gold nanoparticles enable the generation of alkyl radical and silyl radical, enabling radical cross-coupling. The reusability and environmentally-friendly nature of supported gold catalyst as well as the scalability of the reaction system enable the practical transformation of carboxylic acid derivatives into value-added organosilicon and organoboron compounds.