C−H Activation and Hydrogen Isotope Exchange of Aryl Carbamates Using Iridium (I) Complexes Bearing Chelating NHC‐Phosphine Ligands

to related objects

Abstract: Hydrogen isotope exchange (HIE) via C−H activation constitutes an efficient method for the synthesis of isotopically‐enriched compounds, which are crucial components of the drug discovery process and are extensively employed in mechanistic studies. A series of iridium (I) complexes, bearing a chelating phosphine‐N‐heterocyclic carbene ligand, was designed and synthesized for application in the catalytic HIE of challenging N‐ and O‐aryl carbamates. A broad range of substrates were labeled efficiently, and applicability to biologically‐relevant systems was demonstrated by labeling an ʟ‐tyrosine‐derived carbamate with excellent levels of deuterium incorporation. Combined theoretical and experimental studies unveiled intriguing mechanistic features within this process, in comparison to C−H activation and hydrogen isotope exchange catalyzed by monodentate Ir (I) NHC/phosphine complexes.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: C−H Activation and Hydrogen Isotope Exchange of Aryl Carbamates Using Iridium (I) Complexes Bearing Chelating NHC‐Phosphine Ligands ; day:30 ; month:10 ; year:2024 ; extent:9
Chemistry - a European journal ; (30.10.2024) (gesamt 9)

Creator: Zorzatto, Renan
Mulrainey, Paul T.
Reid, Marc
Tuttle, Tell
Lindsay, David M.
Kerr, William J.

DOI: 10.1002/chem.202403090

URN: urn:nbn:de:101:1-2410301418199.481198964793

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:32 AM CEST

Data provider

This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.

Show original at data provider

Associated

Zorzatto, Renan
Mulrainey, Paul T.
Reid, Marc
Tuttle, Tell
Lindsay, David M.
Kerr, William J.

Other Objects (12)

Hochschulschrift

Rhodium(III) and iridium(III) complexes bearing chelating C(pNHC)^phosphine or C(pNHC)^C(NHC) ligands: synthesis and catalytic applications

Impact of the Methylene Bridge Substitution in Chelating NHC‐Phosphine Mn (I) Catalyst for Ketone Hydrogenation

Cationic NHC‐Phosphine Iridium Complexes: Highly Active Catalysts for Base‐Free Hydrogenation of Ketones

Novel palladium complexes employing mixed phosphine phosphonates and phosphine phosphinates as anionic chelating [P,O] ligands

Cationic Iridium(III) Complexes Bearing Different Bulky N,N′-Chelating Ligands

Transmetalation from Magnesium−NHCs—Convenient Synthesis of Chelating π-Acidic NHC Complexes

Iridium-Photocatalyzed Hydrodecyanation of Alkyl Isonitriles with NHC–Borane

Enantioselective Iridium-Catalyzed C–H Amidation of Diaryl Phosphine Oxides

Hochschulschrift

Novel NHC-iridium complexes for advanced application of hyperpolarized NMR

Bulky Iridium NHC Complexes for Bright, Efficient Deep‐Blue OLEDs

Iridium-Catalyzed Preparation of SF5-Substituted Aryl Trifluoroborates

Aryl Azides as Phosphine-Activated Switches for Small Molecule Function

Hochschulschrift

Rhodium(III) and iridium(III) complexes bearing chelating C(pNHC)^phosphine or C(pNHC)^C(NHC) ligands: synthesis and catalytic applications

Impact of the Methylene Bridge Substitution in Chelating NHC‐Phosphine Mn (I) Catalyst for Ketone Hydrogenation

Cationic NHC‐Phosphine Iridium Complexes: Highly Active Catalysts for Base‐Free Hydrogenation of Ketones

Novel palladium complexes employing mixed phosphine phosphonates and phosphine phosphinates as anionic chelating [P,O] ligands

Cationic Iridium(III) Complexes Bearing Different Bulky N,N′-Chelating Ligands

Transmetalation from Magnesium−NHCs—Convenient Synthesis of Chelating π-Acidic NHC Complexes

Iridium-Photocatalyzed Hydrodecyanation of Alkyl Isonitriles with NHC–Borane

Enantioselective Iridium-Catalyzed C–H Amidation of Diaryl Phosphine Oxides

Hochschulschrift

Novel NHC-iridium complexes for advanced application of hyperpolarized NMR

Bulky Iridium NHC Complexes for Bright, Efficient Deep‐Blue OLEDs

Iridium-Catalyzed Preparation of SF5-Substituted Aryl Trifluoroborates

Aryl Azides as Phosphine-Activated Switches for Small Molecule Function

Hochschulschrift

Rhodium(III) and iridium(III) complexes bearing chelating C(pNHC)^phosphine or C(pNHC)^C(NHC) ligands: synthesis and catalytic applications

Impact of the Methylene Bridge Substitution in Chelating NHC‐Phosphine Mn (I) Catalyst for Ketone Hydrogenation

Cationic NHC‐Phosphine Iridium Complexes: Highly Active Catalysts for Base‐Free Hydrogenation of Ketones

Novel palladium complexes employing mixed phosphine phosphonates and phosphine phosphinates as anionic chelating [P,O] ligands

Cationic Iridium(III) Complexes Bearing Different Bulky N,N′-Chelating Ligands

Transmetalation from Magnesium−NHCs—Convenient Synthesis of Chelating π-Acidic NHC Complexes

Iridium-Photocatalyzed Hydrodecyanation of Alkyl Isonitriles with NHC–Borane

Enantioselective Iridium-Catalyzed C–H Amidation of Diaryl Phosphine Oxides

Hochschulschrift

Novel NHC-iridium complexes for advanced application of hyperpolarized NMR

Bulky Iridium NHC Complexes for Bright, Efficient Deep‐Blue OLEDs

Iridium-Catalyzed Preparation of SF5-Substituted Aryl Trifluoroborates

Aryl Azides as Phosphine-Activated Switches for Small Molecule Function

Cultural heritage institutions wishing to register will find more information here.

Fields marked * need to be filled in.

Username*

Please enter your username

Email*

Please enter your email address

Please do not fill this field

First name

Last name

Password*

Please enter your password

Confirm password*

Please enter the same password

I have read the terms of use and the privacy policy for the collection of personal data and accept them. *

This field is required.

I would like to subscribe to the newsletter of the Deutsche Digitale Bibliothek. See newsletter subscription info.

Account created

Your "My DDB" account has been successfully created. Before you can log in to your account, you must click the confirmation link in the message we just sent to the email address you provided.

C−H Activation and Hydrogen Isotope Exchange of Aryl Carbamates Using Iridium (I) Complexes Bearing Chelating NHC‐Phosphine Ligands

Object Details

References and Relationships

Contributors, Places and Time

Further information

Data provider

Associated

Other Objects (12)

Rhodium(III) and iridium(III) complexes bearing chelating C(pNHC)^phosphine or C(pNHC)^C(NHC) ligands: synthesis and catalytic applications

Impact of the Methylene Bridge Substitution in Chelating NHC‐Phosphine Mn (I) Catalyst for Ketone Hydrogenation

Cationic NHC‐Phosphine Iridium Complexes: Highly Active Catalysts for Base‐Free Hydrogenation of Ketones

Novel palladium complexes employing mixed phosphine phosphonates and phosphine phosphinates as anionic chelating [P,O] ligands

Cationic Iridium(III) Complexes Bearing Different Bulky N,N′-Chelating Ligands

Transmetalation from Magnesium−NHCs—Convenient Synthesis of Chelating π-Acidic NHC Complexes

Iridium-Photocatalyzed Hydrodecyanation of Alkyl Isonitriles with NHC–Borane

Enantioselective Iridium-Catalyzed C–H Amidation of Diaryl Phosphine Oxides

Novel NHC-iridium complexes for advanced application of hyperpolarized NMR

Bulky Iridium NHC Complexes for Bright, Efficient Deep‐Blue OLEDs

Iridium-Catalyzed Preparation of SF5-Substituted Aryl Trifluoroborates

Aryl Azides as Phosphine-Activated Switches for Small Molecule Function

Rhodium(III) and iridium(III) complexes bearing chelating C(pNHC)^phosphine or C(pNHC)^C(NHC) ligands: synthesis and catalytic applications

Impact of the Methylene Bridge Substitution in Chelating NHC‐Phosphine Mn (I) Catalyst for Ketone Hydrogenation

Cationic NHC‐Phosphine Iridium Complexes: Highly Active Catalysts for Base‐Free Hydrogenation of Ketones

Novel palladium complexes employing mixed phosphine phosphonates and phosphine phosphinates as anionic chelating [P,O] ligands

Cationic Iridium(III) Complexes Bearing Different Bulky N,N′-Chelating Ligands

Transmetalation from Magnesium−NHCs—Convenient Synthesis of Chelating π-Acidic NHC Complexes

Iridium-Photocatalyzed Hydrodecyanation of Alkyl Isonitriles with NHC–Borane

Enantioselective Iridium-Catalyzed C–H Amidation of Diaryl Phosphine Oxides

Novel NHC-iridium complexes for advanced application of hyperpolarized NMR

Bulky Iridium NHC Complexes for Bright, Efficient Deep‐Blue OLEDs

Iridium-Catalyzed Preparation of SF5-Substituted Aryl Trifluoroborates

Aryl Azides as Phosphine-Activated Switches for Small Molecule Function

Rhodium(III) and iridium(III) complexes bearing chelating C(pNHC)^phosphine or C(pNHC)^C(NHC) ligands: synthesis and catalytic applications

Impact of the Methylene Bridge Substitution in Chelating NHC‐Phosphine Mn (I) Catalyst for Ketone Hydrogenation

Cationic NHC‐Phosphine Iridium Complexes: Highly Active Catalysts for Base‐Free Hydrogenation of Ketones

Novel palladium complexes employing mixed phosphine phosphonates and phosphine phosphinates as anionic chelating [P,O] ligands

Cationic Iridium(III) Complexes Bearing Different Bulky N,N′-Chelating Ligands

Transmetalation from Magnesium−NHCs—Convenient Synthesis of Chelating π-Acidic NHC Complexes

Iridium-Photocatalyzed Hydrodecyanation of Alkyl Isonitriles with NHC–Borane

Enantioselective Iridium-Catalyzed C–H Amidation of Diaryl Phosphine Oxides

Novel NHC-iridium complexes for advanced application of hyperpolarized NMR

Bulky Iridium NHC Complexes for Bright, Efficient Deep‐Blue OLEDs

Iridium-Catalyzed Preparation of SF5-Substituted Aryl Trifluoroborates

Aryl Azides as Phosphine-Activated Switches for Small Molecule Function

Related objects

Reset password