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%).
Department of Chemistry, The University of Sheffield, Dainton Building, Sheffield S3 7HF, United Kingdom.
Ahmad Reza
AR
Massah
Andrew J
AJ
Ross
Richard F W
RF
Jackson
D002384:Catalysis; D006219:Halogens / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D015032:Zinc / Q000737:chemistry*; D017967:Zinc Compounds / Q000737:chemistry*
D006219:Halogens; D007454:Iodides; D011759:Pyrrolidines; D017967:Zinc Compounds; D015032:Zinc; C032519:pyrrolidine