Highly Regioselective Intermolecular Arylation of 1,2,3,4-Tetrahydropyridines

Using a catalytic amount of PdCl2(dppf)·CH2Cl2 in combination with Ag3PO4 and NaOAc, a range of arylated 1,2,3,4-tetrahydropyridines are synthesized in good yields and with complete selectivity at the β-position. The reaction is compatible with a variety of electron-donating and electron-withdrawing...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2008-11, Vol.10 (21), p.4791-4794
Main Authors: Pelletier, Guillaume, Larivée, Alexandre, Charette, André B
Format: Article
Language:English
Subjects:
Catalysis
Dihydropyridines - chemical synthesis
Dihydropyridines - chemistry
Iodides - chemistry
Molecular Structure
Palladium - chemistry
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Using a catalytic amount of PdCl2(dppf)·CH2Cl2 in combination with Ag3PO4 and NaOAc, a range of arylated 1,2,3,4-tetrahydropyridines are synthesized in good yields and with complete selectivity at the β-position. The reaction is compatible with a variety of electron-donating and electron-withdrawing aryl iodides as well as with heteroaryl iodides. The application of these tetrahydropyridines toward the synthesis of polysubstituted piperidines is also demonstrated.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol8018709