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Mesoionic Carbene (MIC)-Catalyzed H/D Exchange at Formyl Groups

Title
Mesoionic Carbene (MIC)-Catalyzed H/D Exchange at Formyl Groups
Authors
Liu, WeiZhao, Liang-LiangMelaim, MohandCao, LeiXu, XingyuBouffard, JeanBertrand, GuyYan, Xiaoyu
Ewha Authors
Jean Bouffard
SCOPUS Author ID
Jean Bouffardscopus
Issue Date
2019
Journal Title
CHEM
ISSN
2451-9294JCR Link
Citation
CHEM vol. 5, no. 9, pp. 2484 - 2494
Publisher
CELL PRESS
Indexed
SCIE; SCOPUS WOS scopus
Document Type
Article
Abstract
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.
DOI
10.1016/j.chempr.2019.08.011
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자연과학대학 > 화학·나노과학전공 > Journal papers
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