Solvent-Dependent Rhodium-Catalyzed Divergent Hydrofunctionalization of Trifluoromethylalkenes

We report a rhodium-catalyzed anti-Markovnikov regioselectivehydrosilylationof trifluoromethylalkenes with substituted silanes giving various & alpha;-trifluoromethyl-& beta;-silanes in good to excellent yields.The hydrogenation products were obtained via the same key intermediatetreated with methanol as a protic solvent. Both transformations hada broad functional tolerance and were expected to facilitate the constructionof complex & alpha;-trifluoromethyl compounds.

Automated summary

We report a rhodium-catalyzed method for the regioselective hydrosilylation of trifluoromethylalkenes with substituted silanes, giving α-trifluoromethyl-β-silanes in good to excellent yields. The hydrogenation products were obtained by treating the key intermediate with methanol as a protic solvent. Both transformations exhibited a broad functional tolerance and were expected to facilitate the synthesis of complex α-trifluoromethyl compounds.