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...

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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
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cited_by cdi_FETCH-LOGICAL-a351t-c86c41653c8d150f6000a7838e8ccb32d92cc8e03af1cded45699be63fc3bbe03
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container_title Journal of the American Chemical Society
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creator Campeau, Louis-Charles
Bertrand-Laperle, Mégan
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Villemure, Elisia
Gorelsky, Serge
Fagnou, Keith
description 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.
doi_str_mv 10.1021/ja7107068
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
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
title C2, C5, and C4 Azole N-Oxide Direct Arylation Including Room-Temperature Reactions
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