The reaction of 3-bromo or 3-chloropropyl tert-butyl thioether (1a or 1'a) with an excess of lithium powder and a catalytic amount of naphthalene (2, 5 mol%) in THF at− 78° C followed by treatment with an electrophile (H2O, D2O, Me2S2, CO2) at the same temperature leads, after hydrolysis, to the expected products 2. Alternatively the process can be carried out under Barbier-type reaction conditions [lithiation in the presence of the electrophile: ...
