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Keywords = C−H deuteriomethoxylation

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11 pages, 2291 KiB  
Article
Cobalt(II)-Catalyzed C−H Deuteriomethoxylation of Benzamides with CD3OD
by Yu-Yan Tan, Mao-Gui Huang, Wei Feng, Mengyuan Niu, Jia-Wei Li and Yue-Jin Liu
Catalysts 2025, 15(1), 65; https://doi.org/10.3390/catal15010065 - 13 Jan 2025
Viewed by 836
Abstract
Herein, we report a practical example of salicylaldehyde-based cobalt-catalyzed C−H deuteriomethoxylation of benzamides using deuterated methanol, facilitated by 8-aminoquinoline as a directing group. The salicylaldehyde-based cobalt catalyst is user-friendly, and the reaction exhibits broad functional group tolerance, accommodating benzene, heterocycles, and naphthalene rings. [...] Read more.
Herein, we report a practical example of salicylaldehyde-based cobalt-catalyzed C−H deuteriomethoxylation of benzamides using deuterated methanol, facilitated by 8-aminoquinoline as a directing group. The salicylaldehyde-based cobalt catalyst is user-friendly, and the reaction exhibits broad functional group tolerance, accommodating benzene, heterocycles, and naphthalene rings. The synthetic utility of this methodology was demonstrated through a gram-scale reaction and the subsequent removal of the 8-aminoquinoline directing group to yield deuteriomethoxylated benzoic acid. Preliminary mechanistic studies suggest that C−H activation is not the rate-determining step of the reaction. Full article
(This article belongs to the Special Issue Recent Catalysts for Organic Synthesis)
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