B(C6F5)3‐Catalyzed α‐Deuteration of Bioactive Carbonyl Compounds with D2O. Issue 2 (11th December 2019)

• Record Type: Journal Article
• Authors: Chang, Yejin; Myers, Tanner; Wasa, Masayuki
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 2(2020)
• Page Start: 360
• Page End: 364
• Publication Date: 2019-12-11
• Subjects: Deuterated drug -- Frustrated Lewis pair -- Late-stage functionalization -- Cooperative catalysis; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201901419
• Languages: English
• ISSNs: 1615-4150

Abstract

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(C6 F5 )3 and D2 O, converting a drug molecule into the corresponding boron‐enolate. Ensuing deuteration of the enolate by in situ‐generated D2 O + −H then results in the formation of α ‐deuterated bioactive carbonyl compounds with up to >98% deuterium incorporation. Abstract :