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B(C6F5)3-Catalyzed ?-Deuteration of Bioactive Carbonyl Compounds with D2O.

ABSTRACT: An efficient deuteration process of ?-C-H bonds in various carbonyl-based pharmaceutical compounds has been developed. Catalytic reactions are initiated by the action of Lewis acidic B(C6F5)3 and D2O, converting a drug molecule into the corresponding boron-enolate. Ensuing deuteration of the enolate by in situ-generated D2O+-H then results in the formation of ?-deuterated bioactive carbonyl compounds with up to >98% deuterium incorporation.

SUBMITTER: Chang Y

PROVIDER: S-EPMC7108789 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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B(C6F5)3-Catalyzed α-Deuteration of Bioactive Carbonyl Compounds with D2O.

Chang Yejin Y Myers Tanner T Wasa Masayuki M

Advanced synthesis & catalysis 20191126 2

An efficient deuteration process of α-C-H bonds in various carbonyl-based pharmaceutical compounds has been developed. Catalytic reactions are initiated by the action of Lewis acidic B(C6F5)3 and D2O, converting a drug molecule into the corresponding boron-enolate. Ensuing deuteration of the enolate by in situ-generated D2O+-H then results in the formation of α-deuterated bioactive carbonyl compounds with up to >98% ...[more]

PMID: 32256276

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