Stable Au(I) catalysts for oxidant-free C-H functionalization with iodoarenes

Mertens, Randall Tyler; Greif, Charles E.; Coogle, James T.; Berger, Gilles; Parkin, Sean; Watson, Mark D.; Awuah, Samuel G.

doi:10.1016/j.jcat.2022.02.019

Cited by 3 publications

(1 citation statement)

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“…An interesting discovery of Au complexes that perturb mitochondria structure offers new tools and potential therapeutics for the treatment of diseases. , Phosphine and arsine supported Au(I) complexes ligated by N^N-bidentate ligands afford unsymmetrical cationic structures in three-coordinate geometry, referred to as AuTri (Figure ). , The different Au–N bonds of the metal center to the bidentate ligand dictates the asymmetry. The rational was to rely on the labile Au–N bond for binding to macromolecules under physiological conditions.…”

Section: Therapeutic Gold Complexesmentioning

confidence: 99%

Next Generation Gold Drugs and Probes: Chemistry and Biomedical Applications

et al. 2023

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The gold drugs, gold sodium thiomalate (Myocrisin), aurothioglucose (Solganal), and the orally administered auranofin (Ridaura), are utilized in modern medicine for the treatment of inflammatory arthritis including rheumatoid and juvenile arthritis; however, new gold agents have been slow to enter the clinic. Repurposing of auranofin in different disease indications such as cancer, parasitic, and microbial infections in the clinic has provided impetus for the development of new gold complexes for biomedical applications based on unique mechanistic insights differentiated from auranofin. Various chemical methods for the preparation of physiologically stable gold complexes and associated mechanisms have been explored in biomedicine such as therapeutics or chemical probes. In this Review, we discuss the chemistry of next generation gold drugs, which encompasses oxidation states, geometry, ligands, coordination, and organometallic compounds for infectious diseases, cancer, inflammation, and as tools for chemical biology via gold–protein interactions. We will focus on the development of gold agents in biomedicine within the past decade. The Review provides readers with an accessible overview of the utility, development, and mechanism of action of gold-based small molecules to establish context and basis for the thriving resurgence of gold in medicine.

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Section: Therapeutic Gold Complexesmentioning

confidence: 99%

Next Generation Gold Drugs and Probes: Chemistry and Biomedical Applications

et al. 2023

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L‐Shaped Heterobidentate Imidazo[1,5‐a]pyridin‐3‐ylidene (N,C)‐Ligands for Oxidant‐Free Au^I/Au^III Catalysis

Gao

Zhou

et al. 2023

Angewandte Chemie

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In the last decade, major advances have been made in homogeneous gold catalysis. However, Au I / Au III catalytic cycle remains much less explored due to the reluctance of Au I to undergo oxidative addition and the stability of the Au III intermediate. Herein, we report activation of aryl halides at gold(I) enabled by NHC (NHC=N-heterocyclic carbene) ligands through the development of a new class of L-shaped heterobidentate ImPy (ImPy = imidazo[1,5-a]pyridin-3-ylidene) N,C ligands that feature hemilabile character of the amino group in combination with strong σ-donation of the carbene center in a rigid conformation, imposed by the ligand architecture. Detailed characterization and control studies reveal key ligand features for Au I /Au III redox cycle, wherein the hemilabile nitrogen is placed at the coordinating position of a rigid framework. Given the tremendous significance of homogeneous gold catalysis, we anticipate that this ligand platform will find widespread application.

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L‐Shaped Heterobidentate Imidazo[1,5‐a]pyridin‐3‐ylidene (N,C)‐Ligands for Oxidant‐Free Au^I/Au^III Catalysis

Gao

Zhou

et al. 2023

Angew Chem Int Ed

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In the last decade, major advances have been made in homogeneous gold catalysis. However, AuI/AuIII catalytic cycle remains much less explored due to the reluctance of AuI to undergo oxidative addition and the stability of the AuIII intermediate. Herein, we report activation of aryl halides at gold(I) enabled by NHC (NHC=N‐heterocyclic carbene) ligands through the development of a new class of L‐shaped heterobidentate ImPy (ImPy=imidazo[1,5‐a]pyridin‐3‐ylidene) N,C ligands that feature hemilabile character of the amino group in combination with strong σ‐donation of the carbene center in a rigid conformation, imposed by the ligand architecture. Detailed characterization and control studies reveal key ligand features for AuI/AuIII redox cycle, wherein the hemilabile nitrogen is placed at the coordinating position of a rigid framework. Given the tremendous significance of homogeneous gold catalysis, we anticipate that this ligand platform will find widespread application.

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Stable Au(I) catalysts for oxidant-free C-H functionalization with iodoarenes

Cited by 3 publications

References 65 publications

Next Generation Gold Drugs and Probes: Chemistry and Biomedical Applications

Next Generation Gold Drugs and Probes: Chemistry and Biomedical Applications

L‐Shaped Heterobidentate Imidazo[1,5‐a]pyridin‐3‐ylidene (N,C)‐Ligands for Oxidant‐Free Au^I/Au^III Catalysis

L‐Shaped Heterobidentate Imidazo[1,5‐a]pyridin‐3‐ylidene (N,C)‐Ligands for Oxidant‐Free Au^I/Au^III Catalysis

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Stable Au(I) catalysts for oxidant-free C-H functionalization with iodoarenes

Cited by 3 publications

References 65 publications

Next Generation Gold Drugs and Probes: Chemistry and Biomedical Applications

Next Generation Gold Drugs and Probes: Chemistry and Biomedical Applications

L‐Shaped Heterobidentate Imidazo[1,5‐a]pyridin‐3‐ylidene (N,C)‐Ligands for Oxidant‐Free AuI/AuIII Catalysis

L‐Shaped Heterobidentate Imidazo[1,5‐a]pyridin‐3‐ylidene (N,C)‐Ligands for Oxidant‐Free AuI/AuIII Catalysis

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Product

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L‐Shaped Heterobidentate Imidazo[1,5‐a]pyridin‐3‐ylidene (N,C)‐Ligands for Oxidant‐Free Au^I/Au^III Catalysis

L‐Shaped Heterobidentate Imidazo[1,5‐a]pyridin‐3‐ylidene (N,C)‐Ligands for Oxidant‐Free Au^I/Au^III Catalysis