Ionic liquid/boronic acid system enabled deuteration with D2O. (20th July 2022)

• Record Type: Journal Article
• Authors: Liu, Bin; Wang, Guanyu; Xu, Zhenhao; Wang, Menglin; Nie, Yangleiyu; Luo, Zhibin
• Is Part Of: Tetrahedron letters. Volume 102(2022)
• Publication Date: 2022-07-20
• Subjects: Ionic liquid -- Boronic acids -- Deuteration -- Transition metal-free -- Deuterodeborylation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.153968
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The development of transition-metal free systems for multi-sites deuteration is important for the preparation of deuterium-labeled drugs and intermediates. We reported that ionic liquid [bmim]PF6 was able to promote highly efficient deuterodeborylation of boronic acids with D2 O. The ionic liquid/boronic acid system was successfully applied to the selective H/D exchange at various sp 2 /sp 3 CH positions. Moreover, unusual nucleophilic behaviors of nitrogen-containing heteroaromatics in ionic liquid were observed.