Recent advances in iridium(I) catalysis towards directed hydrogen isotope exchange

William Kerr, Laura Paterson, Gary Knox

Research output: Contribution to journalReview article

Abstract

The initial discovery and establishment of a family of novel iridium catalysts possessing N-heterocyclic carbene units alongside bulky phosphine ligands allowed selected substrates to be labelled using deuterium or tritium gas at desirably low catalyst loadings via an ortho-directed C-H insertion process. Such a method has broad applicability and offers distinct advantages within the pharmaceutical industry, directly facilitating the ability to carefully monitor a potential drug molecule’s biological fate. Over the past decade since these initial protocols were divulged, many additional advances have been made in terms of catalyst design and substrate scope. This review describes the broadened array of new iridium catalysts and associated protocols for direct and selective C-H activation and hydrogen isotope insertion within a number of new chemical entities of direct relevance to the pharmaceutical industry.
LanguageEnglish
JournalJournal of Labelled Compounds and Radiopharmaceuticals
DOIs
Publication statusAccepted/In press - 16 Oct 2019

Fingerprint

Iridium
phosphine
Drug Industry
Catalysis
Isotopes
Hydrogen
Ion exchange
Catalysts
Tritium
Deuterium
Gases
Pharmaceutical Preparations
Ligands
Substrates
Industry
Chemical activation
Molecules
carbene

Keywords

  • hydrogen isotope exchange
  • N-heterocyclic carbene
  • deuteration
  • tritiation
  • iridium

Cite this

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title = "Recent advances in iridium(I) catalysis towards directed hydrogen isotope exchange",
abstract = "The initial discovery and establishment of a family of novel iridium catalysts possessing N-heterocyclic carbene units alongside bulky phosphine ligands allowed selected substrates to be labelled using deuterium or tritium gas at desirably low catalyst loadings via an ortho-directed C-H insertion process. Such a method has broad applicability and offers distinct advantages within the pharmaceutical industry, directly facilitating the ability to carefully monitor a potential drug molecule’s biological fate. Over the past decade since these initial protocols were divulged, many additional advances have been made in terms of catalyst design and substrate scope. This review describes the broadened array of new iridium catalysts and associated protocols for direct and selective C-H activation and hydrogen isotope insertion within a number of new chemical entities of direct relevance to the pharmaceutical industry.",
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TY - JOUR

T1 - Recent advances in iridium(I) catalysis towards directed hydrogen isotope exchange

AU - Kerr, William

AU - Paterson, Laura

AU - Knox, Gary

PY - 2019/10/16

Y1 - 2019/10/16

N2 - The initial discovery and establishment of a family of novel iridium catalysts possessing N-heterocyclic carbene units alongside bulky phosphine ligands allowed selected substrates to be labelled using deuterium or tritium gas at desirably low catalyst loadings via an ortho-directed C-H insertion process. Such a method has broad applicability and offers distinct advantages within the pharmaceutical industry, directly facilitating the ability to carefully monitor a potential drug molecule’s biological fate. Over the past decade since these initial protocols were divulged, many additional advances have been made in terms of catalyst design and substrate scope. This review describes the broadened array of new iridium catalysts and associated protocols for direct and selective C-H activation and hydrogen isotope insertion within a number of new chemical entities of direct relevance to the pharmaceutical industry.

AB - The initial discovery and establishment of a family of novel iridium catalysts possessing N-heterocyclic carbene units alongside bulky phosphine ligands allowed selected substrates to be labelled using deuterium or tritium gas at desirably low catalyst loadings via an ortho-directed C-H insertion process. Such a method has broad applicability and offers distinct advantages within the pharmaceutical industry, directly facilitating the ability to carefully monitor a potential drug molecule’s biological fate. Over the past decade since these initial protocols were divulged, many additional advances have been made in terms of catalyst design and substrate scope. This review describes the broadened array of new iridium catalysts and associated protocols for direct and selective C-H activation and hydrogen isotope insertion within a number of new chemical entities of direct relevance to the pharmaceutical industry.

KW - hydrogen isotope exchange

KW - N-heterocyclic carbene

KW - deuteration

KW - tritiation

KW - iridium

UR - https://onlinelibrary.wiley.com/loi/10991344

U2 - 10.1002/jlcr.3812

DO - 10.1002/jlcr.3812

M3 - Review article

JO - Journal of Labelled Compounds and Radiopharmaceuticals

T2 - Journal of Labelled Compounds and Radiopharmaceuticals

JF - Journal of Labelled Compounds and Radiopharmaceuticals

SN - 0362-4803

ER -