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 Pd2(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%)....

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Bibliographic Details
Published in:Journal of organic chemistry 2010-12, Vol.75 (23), p.8275-8278
Main Authors: Massah, Ahmad Reza, Ross, Andrew J, Jackson, Richard F. W
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Halogens - chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Iodides - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
Preparations and properties
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Zinc - chemistry
Zinc Compounds - chemistry
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Summary:Addition of (S)-(+)-tert-butyl 2-(iodomethyl)pyrrolidine-1-carboxylate to activated zinc, aryl halides, and a catalyst derived from Pd2(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%).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo101503p