Corey–Kim oxidation

Although the Corey–Kim oxidation possesses the distinctive advantage over Swern oxidation of allowing an operation above –25 °C, it is not so commonly used due to issues with selectivity in substrates susceptible to chlorination by N-chlorosuccinimide.

Addition of triethylamine to the activated alcohol leads to its oxidation to aldehyde or ketone and generation of dimethyl sulfide.

Under Corey–Kim conditions allylic and benzylic alcohols have a tendency to evolve to the corresponding allyl and benzyl chlorides unless the alcohol activation is very quickly followed by addition of triethylamine.

Substituting dimethyl sulfide with something less noxious has been the goal of several research projects.

Crich et al.[7] utilized fluorous technology in a similar manner.