Palladium-Catalyzed Divergent Arylation of Triazolopyridines: A Computational Study

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The mechanisms for new palladium-catalyzed divergent reactions of triazolopyridines were investigated by means of DFT calculations. Previously, it was observed experimentally that cross-coupling at the C7-position of triazolopyridines occurred when a strong base was used, whereas the reaction could be diverted to the C3-position if a weak base was employed. Calculations suggest that a strong base, such as tert-butoxide, can easily deprotonate C7-H, independent of the palladium metal, and deliver the preactivated substrate to palladium, which can reductively eliminate the final product. Without a strong base, the palladium(II) center reacts with the ring-opened diazo imine isomer of triazolopyridine to initially form a palladium(II)-carbene intermediate, which undergoes migratory insertion followed by -hydride elimination to afford a 1,1-disubstituted alkene.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2018-09
Language
English
Article Type
Article
Citation

CHEMISTRY-AN ASIAN JOURNAL, v.13, no.17, pp.2505 - 2510

ISSN
1861-4728
DOI
10.1002/asia.201800498
URI
http://hdl.handle.net/10203/246580
Appears in Collection
CH-Journal Papers(저널논문)
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