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Using heterogeneous photocatalysis, the radical addition of tertiary amines with electron deficientalkenes can be performed in high yields (up to 98%) and high facial diastereoselectivity. The photochemicalinduced electron transfer process initiates the radical chain reaction and inorganic semiconductorslike TiO2 and ZnS were used. According to the proposed mechanism, the reaction takes place at the surfaceof the semiconductor and the termination step results from an interfacial electron transfer from the conductionband to the oxoallyl radical intermediate. Frequently, semiconductors are used for the mineralisationof organic compounds in wastewater. However, in this case, they are used in organic synthesis. The processcan be performed in a convenient way and is particularly interesting from the ecological and economicalpoint of view. No previous functionalization of the tertiary amines is necessary for C − C bond formation.Further on, the amines are used both as reactant and as solvent. The excess is recycled by distillation and theinexpensive sensitiser can be easily removed by filtration. In this way, products of high interest for organicsynthesis are obtained by a diastereoselective radical reaction

Semiconductors as sensitisers for the radical addition of tertiary amines to electron deficient alkenes