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Hydrogen‐Isotope Exchange (HIE) Reactions of Secondary and Tertiary Sulfonamides and Sulfonylureas with Iridium(I) Catalysts
Author(s) -
Burhop Annina,
Weck Remo,
Atzrodt Jens,
Derdau Volker
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601599
Subject(s) - chemistry , catalysis , iridium , hydrogen isotope , labelling , deuterium , combinatorial chemistry , organic chemistry , hydrogen , biochemistry , physics , quantum mechanics
For the first time we report the optimized hydrogen‐isotope exchange (HIE) conditions for the selective aromatic deuteriation of various sulfonylureas and tertiary sulfonamides, as well as for a broad range of secondary sulfonamides. Based on a comprehensive screening of readily available Ir catalysts, the Kerr‐type NHC catalyst 5 proved to be most efficient in the HIE reaction of secondary sulfonamides and sulfonylureas. However, for tertiary sulfonamides, the commercially available Burgess catalyst 6 , not yet utilized in HIE reactions, resulted in a much higher incorporation of deuterium. Finally, we tested the new HIE protocol for the labelling of a series of sulfa drugs and adapted the conditions to allow for selective tritium labelling.