C2, C5, and C4 Azole N-Oxide Direct Arylation Including Room-Temperature Reactions

The N-oxide group imparts a dramatic increase in reactivity at all positions of the azole ring of thiazoles and imidazoles and changes the weak bias for C5 > C2 arylation to a reliable C2 > C5 > C4 reactivity profile. Use of this cross-coupling strategy enables high yielding and room-temper...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2008-03, Vol.130 (11), p.3276-3277
Main Authors: Campeau, Louis-Charles, Bertrand-Laperle, Mégan, Leclerc, Jean-Philippe, Villemure, Elisia, Gorelsky, Serge, Fagnou, Keith
Format: Article
Language:English
Subjects:
Cyclic N-Oxides - chemical synthesis
Cyclic N-Oxides - chemistry
Models, Chemical
Molecular Structure
Organometallic Compounds - chemistry
Palladium - chemistry
Temperature
Thiazoles - chemical synthesis
Thiazoles - chemistry
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:The N-oxide group imparts a dramatic increase in reactivity at all positions of the azole ring of thiazoles and imidazoles and changes the weak bias for C5 > C2 arylation to a reliable C2 > C5 > C4 reactivity profile. Use of this cross-coupling strategy enables high yielding and room-temperature C2 arylations, mild reactions at C5, and the first examples of C4 arylationproviding a unique opportunity for exhaustive functionalization of the azole core with complete control of regioselectivity. A correlation of reactivity with the relative contributions of each carbon atom to the HOMO is observed and discussed.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja7107068