Naphthalene-Catalysed Reductive Desulfonylation with Lithium: Alkyllithiums from Alkyl Phenyl Sulfones

Article abstract of DOI:10.1016/S0040-4039(00)76673-1

The reaction of alkyl aryl sulfones 1 with an excess of lithium powder and a catalytic amount of naphthalene (8 mol percent) in the presence of a carbonyl compound iCHO, PhCHO, Et2CO, (CH2)5CO> or trimethylchlorosilane (Barbier-type conditions) in THF at temperatures ranging between -78 and 20 deg C leads, after hydrolysis with water, to the expected coupling products, arising from the corresponding alkyllithium in situ generated, in 30-61percent yields.