Desulfonylation Reactions

Alonso, Diego A.; Nájera, Carmen


The use of sulfones in organic chemistry, acting as an auxiliary group, is still a very important synthetic strategy, especially for the formation of carbon-carbon single and double bonds. Once the synthetic objective is achieved, the sulfone group is usually removed from the molecule. This removal most commonly involves a reductive desulfonylation process with either replacement of the sulfone by hydrogen, or a process that results in the formation of a carbon-carbon double bond when a β-hydroxy or β-alkoxy sulfone is employed.

This chapter is devoted to the replacement of the sulfone group by a hydrogen (reductive desulfonylation reactions), and reductive elimination reactions of Julia-type substrates (Julia-Lythgoe olefination process). The chapter addresses the full scope, generality, limitations, and synthetic applications of these reactions. The literature through most of 2007 is covered.