Suppressed beta-hydride elimination in palladium-catalyzed cascade cyclization-coupling reactions: an efficient synthesis of 3-arylmethylpyrrolidines

Org Lett. 2000 May 4;2(9):1213-6. doi: 10.1021/ol0056426.


[formula: see text] A novel type of palladium-catalyzed cascade cyclization-coupling reaction that proceeds with suppressed beta-hydride elimination has been found. One of the N-sulfonyl oxygens is suggested to coordinatively stabilize an alkylpalladium intermediate, thus preventing the intermediate from the usual beta-elimination. This is the first sequential palladium-catalyzed coupling reaction where the Suzuki and Heck reactions can compete. The reaction provides an efficient synthetic route to 4-methylene-3-arylmethylpyrrolidines, which are not readily available by other routes.