Azo anions in synthesis. Use of trityl- and diphenyl-4-pyridylmethyl-hydrazones for reductive C–C bond formation from aldehydes and ketones

Abstract

The lithium salts for trityl- and diphenyl-4-pyridylmethyl-hydrazones of both aldehydes and ketones react with electrophiles (alkyl haldies, aldehydes, and ketones) at low temperature to form C-trapped azo compounds; these intermediates decompose homolytically with loss of nitrogen below room temperature and can be diverted in a synthetically useful way to alkanes, or alkenes, or alcohols.