A Palladium-Catalyzed Alkylation/Direct Arylation Synthesis of Nitrogen-Containing Heterocycles

A norbornene-mediated palladium-catalyzed sequence is described in which an alkyl-aryl bond and an aryl-heteroaryl bond are formed in one reaction vessel. The aryl-heteroaryl bond-forming step occurs via a direct arylation reaction. A number of six-, seven-, and eight-membered ring-annulated indoles...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2008-03, Vol.73 (5), p.1888-1897
Main Authors: Blaszykowski, Christophe, Aktoudianakis, Evangelos, Alberico, Dino, Bressy, Cyril, Hulcoop, David G, Jafarpour, Farnaz, Joushaghani, Arash, Laleu, Benoît, Lautens, Mark
Format: Article
Language:English
Subjects:
Alkylation
Catalysis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Nitrogen - chemistry
Organic chemistry
Palladium - chemistry
Preparations and properties
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:A norbornene-mediated palladium-catalyzed sequence is described in which an alkyl-aryl bond and an aryl-heteroaryl bond are formed in one reaction vessel. The aryl-heteroaryl bond-forming step occurs via a direct arylation reaction. A number of six-, seven-, and eight-membered ring-annulated indoles, pyrroles, pyrazoles, and azaindoles were synthesized from the corresponding bromoalkyl azole and an aryl iodide.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo702052b