@article{bbbb55a85e3848e893ed6f18e2ce0acd,
title = "Iridium-catalysed ortho-deuteration of primary sulfonamides: an experimental and computational study",
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.",
keywords = "isotopic labelling, heavy hydrogen isotopes, organometallic catalysis",
author = "William Kerr and Marc Reid and Christopher Tuttle",
year = "2014",
month = mar,
day = "1",
doi = "10.1002/jlcr.3173",
language = "English",
volume = "57",
pages = "183--184",
journal = "Journal of Labelled Compounds and Radiopharmaceuticals",
issn = "0362-4803",
publisher = "John Wiley and Sons Ltd",
number = "3",
note = "22nd International Isotope Society (UK Group) Symposium : Synthesis and applications of labelled compounds 2013 ; Conference date: 18-10-2013 Through 18-10-2013",
url = "http://www.intl-isotope-soc.org/events/2013/10/18/244/",
}