Arene-catalysed reductive desulfonylation and desulfinylation reactions: New routes for alkyllithiums

Article abstract of DOI:10.1016/0040-4020(94)01116-H

The reactions of alkyl phenyl sulfones (1) with an excess of lithium powder and a catalytic amount of naphthalene (8 mol %) in the presence of a carbonyl compound or chlorotrimethylsilane (Barbier-type conditions) in THF at temperatures ranging between -78 and 20°C leads, after hydrolysis, to the expected products (2) arising from the corresponding alkyllithium generated in situ. When the same methodology is applied to sulfolene (3) or different alkyl phenyl sulfoxides (6), cyclic sulfinates 5 or products 2 are, respectively, obtained, the yields being, in general modest.