Aryl halides, reduction with organotin hydride

A radical mechanism may also be proposed for the other reductions, at least for the alkyl and aryl halides in view of the clarified relations of their reduction with organotin hydrides (756). For carbonyl or other unsaturated compounds (Table IX), a polar mechanism is also possible it could be of Sn2 type. Further experiments are needed for clarification. 

The reduction of alkyl, aryl, and acyl halides by organotin hydrides would suggest that other halides might also be reduced. It has been shown that AT -bromosuccinimide is reduced in 95 % yield with triphenyltin hydride (82). Diphenylchlorophosphine undergoes exothermic reduction with triphenyltin hydride providing diphenylphosphine in good yield (8J). 

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