Resin-immobilised benzyl and aryl vinyl sulfones: New versatile traceless linkers for solid-phase organic synthesis

New polystyrene-based resins containing benzyl and aryl vinyl sulfone groups are described. The vinyl sulfone group reacts efficiently with 2° amines, via conjugate addition, and the resin-bound 3° amine products can be quatermised through alkylation. Subsequent deamination to give 3° amines and the regenerated vinyl sulfone occurs in moderate to good yield. Both systems can be recycled and show moderate stability to acids and high stability to nucleophiles including Grignard reagents.