The interplay of carbophilic activation and Au(i)/Au(iii) catalysis: an emerging technique for 1,2-difunctionalization of C–C multiple bonds

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(18), P. 10422 - 10450

Published: Jan. 1, 2021

This review highlights a decade-long journey of Au-catalyzed 1,2-difunctionalization reactions C–C multiple bonds that have been realized due to the productive integration Au( i )/Au( iii )catalysis with unique π-activation mode gold complexes.

Language: Английский

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Photoinduced gold-catalyzed divergent dechloroalkylation of gem-dichloroalkanes

Nature Catalysis, Journal Year: 2022, Volume and Issue: 5(12), P. 1098 - 1109

Published: Dec. 15, 2022

Language: Английский

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Merging Photoinduced Iron-Catalyzed Decarboxylation with Copper Catalysis for C–N and C–C Couplings

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(3), P. 1678 - 1685

Published: Jan. 13, 2023

We report a photoinduced iron/copper dual-catalytic strategy for the radical decarboxylation functionalization of aliphatic carboxylic acids. The ligand-to-iron charge transfer process under light was initially occurred to generate an unstabilized alkyl radical, and copper catalyst delivered enabled subsequent coupling reactions form C–N or C–C bonds. By merging iron-catalyzed with catalysis, this system allows smooth conversion wide range acids amination, decarboxylative dehydrogenation, alkylation efficiently. A variety complex drug natural molecules is applicable, suggesting that would facilitate rapid compound library synthesis benefit discovery pharmaceutical agents.

Language: Английский

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Electrochemical gold-catalysed biocompatible C(sp2)–C(sp) coupling

Nature Synthesis, Journal Year: 2023, Volume and Issue: 2(4), P. 338 - 347

Published: Jan. 12, 2023

Language: Английский

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Dirhodium(II)/Xantphos-Catalyzed Relay Carbene Insertion and Allylic Alkylation Process: Reaction Development and Mechanistic Insights

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(30), P. 11799 - 11810

Published: July 23, 2021

Although dirhodium-catalyzed multicomponent reactions of diazo compounds, nucleophiles and electrophiles have achieved great advance in organic synthesis, the introduction allylic moiety as third component via metal intermediate remains a formidable challenge this area. Herein, an attractive three-component reaction readily accessible amines, compounds enabled by novel dirhodium(II)/Xantphos catalysis is disclosed, affording various architecturally complex functionally diverse α-quaternary α-amino acid derivatives good yields with high atom step economy. Mechanistic studies indicate that transformation through relay dirhodium(II)-catalyzed carbene insertion alkylation process, which catalytic properties dirhodium are effectively modified coordination Xantphos, leading to activity process.

Language: Английский

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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

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(12)

Published: Jan. 25, 2023

In the last decade, major advances have been made in homogeneous gold catalysis. However, Au

Language: Английский

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Photoinduced activation of alkyl chlorides

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(17), P. 6120 - 6138

Published: Jan. 1, 2023

In recent years, the activation of unactivated alkyl chlorides through light-induced processes has emerged as a promising field in radical chemistry, and led to new transformations organic synthesis. Direct utilization C(sp3)-hybridized electrophiles enables facile construction carbon-carbon carbon-heteroatom bonds. Furthermore, studies medicinal chemistry indicate that their presence is associated with high levels success clinical trials. This review summarizes advances photoinduced discusses mechanistic aspects underlying these reactions. We anticipate this will serve valuable resource for researchers chemical bond functionalization, inspire considerable developments drug synthesis, materials science other related disciplines.

Language: Английский

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Site-Selective Arylation of Carboxamides from Unprotected Peptides

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(27), P. 14865 - 14873

Published: June 28, 2023

The amidated peptides are an important class of biologically active compounds due to their unique biological properties and wide applications as potential peptide drugs biomarkers. Despite the abundance free amide motifs (Asn, Gln, C-terminal amide) in native peptides, late-stage modification unit naturally occurring remains very rare because intrinsically weak nucleophilicity amides interference multiple competing nucleophilic residues, which generally lead undesired side reactions. Herein, chemoselective arylation unprotected polypeptides has been developed under air atmosphere afford N-aryl bearing various functional motifs. Its success relies on combination gold catalysis silver salt differentiate relative inert among a collection reactive amino acid residues (e.g., -NH2, -OH, -COOH), favoring C-N bond coupling toward over other more groups. Experimental DFT studies reveal crucial role cation, serves transient coordination mask reaction sites, overcoming inherently low reactivity amides. excellent biocompatibility this strategy applied functionalize range complex peptides. application could be further extended labeling stapling.

Language: Английский

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Unlocking Migratory Insertion in Gold Redox Catalysis

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(29)

Published: May 16, 2023

Exploration of elementary reactions in organometallic catalysis is an important method with which to discover new reactions. In this article, we report a gold(I)-catalyzed iodo-alkynylation benzyne involving the merging challenging migratory insertion and oxidative addition process gold catalytic cycle. A wide range structurally diverse alkynyl iodides are good coupling partners transformation. Both aliphatic aromatic can react benzynes smoothly afford highly functionalized 1,2-disubstituted aromatics moderate yields. Its functional group compatibility late-stage application complex molecules demonstrate its synthetic robustness. Studies mechanism reveals feasibility DFT calculations possible into AuIII -carbon bonds AuI /AuIII redox cycle, representing step towards reaction chemistry research.

Language: Английский

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Asymmetric gold catalysis enabled by specially designed ligands

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1858 - 1895

Published: Jan. 1, 2024

This review is planned to provide a comprehensive overview of the progress made in design and development chiral ligands for asymmetric gold catalysis.

Language: Английский

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