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

Authors
  • Chang, Yejin1
  • Myers, Tanner1
  • Wasa, Masayuki1
  • 1 Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States. , (United States)
Type
Published Article
Journal
Advanced Synthesis & Catalysis
Publisher
Wiley
Publication Date
Jan 23, 2020
Volume
362
Issue
2
Pages
360–364
Identifiers
DOI: 10.1002/adsc.201901419
PMID: 32256276
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

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% deuterium incorporation.

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