Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts

Cai, Yuan; Chatterjee, Sagnik; Ritter, Tobias

doi:10.1021/jacs.3c04016

Cited by 61 publications

(27 citation statements)

References 71 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Based on the literature reports , and information assembled through CV, spectrometric study, and control experiments, a plausible mechanism for the electrocatalytic process is outlined in Scheme . The azidation of N -arylenamines occurs through the release of an azidyl radical from an anodically oxidized [Cu III ]-N 3 complex.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Quinoxalines through Cu-electrocatalytic Azidation/Annulation Cascade at Low Catalyst Loading

Baidya,

De Sarkar

2023

Org. Lett.

View full text Add to dashboard Cite

A Cu-electrocatalytic azidation of N-aryl enamines and subsequent denitrogenative annulation for the construction of quinoxaline frameworks is reported. Only 0.5 mol % of copper(II) chloride was employed for this cascade transformation displaying excellent functional-group compatibility even with complex bioactive scaffolds. The efficient electro-oxidative protocol enables the use of NaN 3 as the cheapest azide source. Detailed mechanistic experiments, cyclic voltammetry, and spectroscopic studies provided strong evidence for a dual role of the Cu catalyst in azidyl and iminyl radical generation steps.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of Quinoxalines through Cu-electrocatalytic Azidation/Annulation Cascade at Low Catalyst Loading

Baidya,

De Sarkar

2023

Org. Lett.

View full text Add to dashboard Cite

show abstract

“…Finally, the homobenzyl radical engages in an outer-sphere pathway to react with the terminal nitrogen atom of the azido group within complex 105, yielding the target product 106 and regenerating the catalyst 101 (Scheme 16). [23]…”

Section: C(sp 2 )à C(sp 3 ) Bond Formationmentioning

confidence: 99%

Synthetic Applications of Sulfonium Salts as Aryl Radical Precursors

Wu,

Gao,

Chen

2023

Eur J Org Chem

View full text Add to dashboard Cite

The utilization of aryl radicals as open‐shelled intermediates has become an essential tool for both conventional and state‐of‐the‐art synthetic chemistry. However, the current methods for generating aryl radicals are still inefficient, greatly impeding their practical applications. Encouragingly, sulfonium salts have emerged as appealing sources of aryl radicals for a wide range of transformations aimed at creating novel chemical bonds driven by their distinctive structural attributes and chemical tendencies. This review primarily focuses on the specific reaction mechanisms underlying the cleavage of C−S bonds in sulfonium salts, leading to the generation of corresponding aryl radicals within diverse reaction conditions.

show abstract

“…[11,12b] During the course of compiling our manuscript, Ritter and co-workers extended the application of this strategy to three-component reactions, enabling aminoarylation of alkenes through a photoinduced copper-catalyzed pathway. [13a] Despite these recent advances, [13] the development of a unified synthetic platform capable of rapidly assembling a broad array of 1,2-aryl heteroatomic compounds from inexpensive and readily available aromatics and olefins remains an unmet challenge.…”

Section: Introductionmentioning

confidence: 99%

Modular and Practical 1,2‐Aryl(Alkenyl) Heteroatom Functionalization of Alkenes through Iron/Photoredox Dual Catalysis**

Zhang,

Liu,

Ang

et al. 2023

Angew Chem Int Ed

View full text Add to dashboard Cite

Efficient methods for synthesizing 1,2‐aryl(alkenyl) heteroatomic cores, encompassing heteroatoms such as nitrogen, oxygen, sulfur, and halogens, are of significant importance in medicinal chemistry and pharmaceutical research. In this study, we present a mild, versatile and practical photoredox/iron dual catalytic system that enables access to highly privileged 1,2‐aryl(alkenyl) heteroatomic pharmacophores with exceptional efficiency and site selectivity. Our approach exhibits an extensive scope, allowing for the direct utilization of a wide range of commodity or commercially available (hetero)arenes as well as activated and unactivated alkenes with diverse functional groups, drug scaffolds, and natural product motifs as substrates. By merging iron catalysis with the photoredox cycle, a vast array of alkene 1,2‐aryl(alkenyl) functionalization products that incorporate a neighboring azido, amino, halo, thiocyano and nitrooxy group were secured. The scalability and ability to rapid synthesize numerous bioactive small molecules from readily available starting materials highlight the utility of this protocol.

show abstract

Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts

Cited by 61 publications

References 71 publications

Synthesis of Quinoxalines through Cu-electrocatalytic Azidation/Annulation Cascade at Low Catalyst Loading

Synthesis of Quinoxalines through Cu-electrocatalytic Azidation/Annulation Cascade at Low Catalyst Loading

Synthetic Applications of Sulfonium Salts as Aryl Radical Precursors

Modular and Practical 1,2‐Aryl(Alkenyl) Heteroatom Functionalization of Alkenes through Iron/Photoredox Dual Catalysis**

Contact Info

Product

Resources

About