Platinum-catalyzed intramolecular hydroamination of unactivated olefins with secondary alkylamines

Christopher F Bender; Ross A Widenhoefer

doi:10.1021/ja043278q

Platinum-catalyzed intramolecular hydroamination of unactivated olefins with secondary alkylamines

J Am Chem Soc. 2005 Feb 2;127(4):1070-1. doi: 10.1021/ja043278q.

Authors

Christopher F Bender¹, Ross A Widenhoefer

Affiliation

¹ P M Gross Chemical Laboratory, Duke University, Durham, North Carolina 27708-0346, USA.

PMID: 15669824
DOI: 10.1021/ja043278q

Abstract

Reaction of benzyl-2,2-diphenyl-4-pentenylamine with a catalytic 1:2 mixture of [PtCl2(H2C=CH2)]2 (2.5 mol %) and PPh3 in dioxane at 120 degrees C for 16 h led to isolation of 1-benzyl-2-methyl-4,4-diphenylpyrrolidine in 75% yield. A number of gamma- and delta-amino olefins underwent intramolecular hydroamination to form the corresponding pyrrolidine derivatives in moderate to good yield. The reaction displayed excellent functional group compatibility and low moisture sensitivity.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alkenes / chemistry*
Amination
Amines / chemical synthesis
Amines / chemistry*
Catalysis
Organoplatinum Compounds / chemistry*

Substances

Alkenes
Amines
Organoplatinum Compounds