In Situ trapping of Boc-2-pyrrolidinylmethylzinc Iodide with Aryl Iodides: Direct Synthesis of 2-Benzylpyrrolidines

Addition of (S)-(+)-tert-butyl 2-(iodomethyl)pyrrolidine-1-carboxylate to activated zinc, aryl halides, and a catalyst derived from Pd-2(dba)(3) (2.5 mol %) and SPhos (5 mol %) in DMF allows trapping of the corresponding organozinc reagent, with formation of Boc-protected 2-benzylpyrrolidines (20-72%).