Palladium-Catalyzed Divergent Arylation of Triazolopyridines: A Computational Study

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Title
Palladium-Catalyzed Divergent Arylation of Triazolopyridines: A Computational Study
Author(s)
Deyaa I. AbuSalim; Hong S.; Baik M.-H.
Publication Date
2018-09
Journal
Chemistry-An Asian Journal, v.13, no.17, pp.2505 - 2510
Publisher
WILEY-V C H VERLAG GMBH
Abstract
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 β-hydride elimination to afford a 1,1-disubstituted alkene. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinhei
URI
https://pr.ibs.re.kr/handle/8788114/4921
ISSN
1861-4728
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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