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Mesoionic Carbene (MIC)-Catalyzed H/D Exchange at Formyl Groups
- Mesoionic Carbene (MIC)-Catalyzed H/D Exchange at Formyl Groups
- Liu, Wei; Zhao, Liang-Liang; Melaim, Mohand; Cao, Lei; Xu, Xingyu; Bouffard, Jean; Bertrand, Guy; Yan, Xiaoyu
- Ewha Authors
- Jean Bouffard
- SCOPUS Author ID
- Jean Bouffard
- Issue Date
- Journal Title
- CHEM vol. 5, no. 9, pp. 2484 - 2494
- CELL PRESS
- SCIE; SCOPUS
- Document Type
- H/D exchange at formyl groups is the most direct approach for the synthesis of deuterated aldehydes. Platinum-group metal complexes have been employed to catalyze this transformation, with significant substrate scope limitations. Although N-heterocyclic carbenes can also activate the C- H bond of aldehydes through the formation of Breslow intermediates, benzoin condensation and other C-C-bond-forming pathways have so far outpaced synthetically useful H/D exchange. Investigation of the reaction of aldehydes with 1,2,3-triazolylidenes has revealed the reversible formation of Breslow intermediates and the inhibition of the condensation steps in methanol solvent. 1,2,3-Triazolylidenes catalyze the H/D exchange of aryl, alkenyl, and alkyl aldehydes in high yields and deuterium incorporation levels using deuterated methanol as an affordable D source. The unique properties of these mesoionic carbenes (MICs) enable a streamlined preparation of deuterated synthetic intermediates and pharmaco-phores that are highly valuable as mechanistic and metabolic probes.
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