Iridium-catalysed ortho-deuteration of primary sulfonamides: an experimental and computational study

Research output: Contribution to journalMeeting abstract

Abstract

Isotopic labelling with heavy hydrogen isotopes (D2 and T2) is widely used as a means to monitor the biological fate of a potential drug molecule and represents a particularly industry-facing example of chemoselective organometallic catalysis. Consequently, preliminary studies from our laboratory have allowed expedient access to a series of novel iridium complexes, such as 2, that are able to catalyse the ortho-deuteration of various coordinating functionalities and pharmacophores, such as ketones, amides and nitro compounds 2 (Scheme 1). As part of our latest studies, we recently reported an efficient protocol for ortho-deuteration using more readily accessible Ir(I)chloro-carbene complexes. Turning to more challenging substrate classes, the utility of bench-stable catalysts such as 5 has now evolved to deliver the first highly effective strategy for the ortho-deuteration of primary sulfonamides at room temperature (Scheme 2). Additionally, we have used experimental and computational methods in parallel to explain the origins of observed chemoselectivity in labelling multi-functional drug molecules like 7, highlighting the importance of substrate–complex interactions during complexation. The details of all such studies will be delineated in this lecture.
Original languageEnglish
Pages (from-to)183-184
Number of pages2
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume57
Issue number3
Early online date26 Jan 2014
DOIs
Publication statusPublished - 1 Mar 2014
Event22nd International Isotope Society (UK Group) Symposium: Synthesis and applications of labelled compounds 2013 - Cambridge, United Kingdom
Duration: 18 Oct 201318 Oct 2013
http://www.intl-isotope-soc.org/events/2013/10/18/244/

Keywords

  • isotopic labelling
  • heavy hydrogen isotopes
  • organometallic catalysis

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