Abstract
| Language | English |
|---|---|
| Pages | 183-184 |
| Number of pages | 2 |
| Journal | Journal of Labelled Compounds and Radiopharmaceuticals |
| Volume | 57 |
| Issue number | 3 |
| Early online date | 26 Jan 2014 |
| DOIs | |
| Publication status | Published - 1 Mar 2014 |
| Event | 22nd International Isotope Society (UK Group) Symposium: Synthesis and applications of labelled compounds 2013 - Cambridge, United Kingdom Duration: 18 Oct 2013 → 18 Oct 2013 http://www.intl-isotope-soc.org/events/2013/10/18/244/ |
Fingerprint
Keywords
- isotopic labelling
- heavy hydrogen isotopes
- organometallic catalysis
Cite this
}
Iridium-catalysed ortho-deuteration of primary sulfonamides : an experimental and computational study. / Kerr, William; Reid, Marc; Tuttle, Christopher.
In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 57, No. 3, 01.03.2014, p. 183-184.Research output: Contribution to journal › Meeting abstract
TY - JOUR
T1 - Iridium-catalysed ortho-deuteration of primary sulfonamides
T2 - Journal of Labelled Compounds and Radiopharmaceuticals
AU - Kerr, William
AU - Reid, Marc
AU - Tuttle, Christopher
PY - 2014/3/1
Y1 - 2014/3/1
N2 - 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.
AB - 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.
KW - isotopic labelling
KW - heavy hydrogen isotopes
KW - organometallic catalysis
UR - http://onlinelibrary.wiley.com/doi/10.1002/jlcr.3173/abstract
U2 - 10.1002/jlcr.3173
DO - 10.1002/jlcr.3173
M3 - Meeting abstract
VL - 57
SP - 183
EP - 184
JO - Journal of Labelled Compounds and Radiopharmaceuticals
JF - Journal of Labelled Compounds and Radiopharmaceuticals
SN - 0362-4803
IS - 3
ER -