Tributylvinyltin → 2-Benzyl-4-vinylisoindoline

Participants

Reaction Conditions

Reaction Steps

A solution of 2-benzyl-4-bromoisoindoline (16.7 g, 58.0 mmol) and tributyl(vinyl)tin (20.3 mL, 69.6 mmol) in PhMe (400 mL) was degassed by bubbling nitrogen gas through the solution for 15 minutes. Tetrakis(triphenylphosphine)palladium (0) (1.30 g, 1.16 mmol) was added, and the resulting solution heated in a 100° C. oil bath, under nitrogen for 24 hours. The contents of the reaction flask were cooled, evaporated and subjected to flash column chromatography, eluting with hexane/ethyl acetate 95/5 to give the title compound as a pale oil that turned pink on standing. LRMS (ESI) m/z 236 [(M+H)+; calcd for C17H18N: 236].

Provenance & Evidence