1016990-17-2Relevant academic research and scientific papers
C2, C5, and C4 azole N-oxide direct arylation including room-temperature reactions
Campeau, Louis-Charles,Bertrand-Laperle, Megan,Leclerc, Jean-Philippe,Villemure, Elisia,Gorelsky, Serge,Fagnou, Keith
, p. 3276 - 3277 (2008/10/09)
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. Copyright
