Visible-light-mediated aerobic Ritter-type C–H amination of diarylmethanes using DDQ/<i>tert</i>-butyl nitrite

Li, Tianci; Yang, Jiangyu; Yin, Xin; Shi, Jian; Cao, Qun; Hu, Miaomiao; Xu, Xia; Li, Meichao; Shen, Zhenlu

doi:10.1039/d2ob01713j

Cited by 8 publications

(1 citation statement)

References 38 publications

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“…By combining the results of these experiments with reports in the literature, 4f 13b d 14 we propose the mechanism for the intramolecular C(sp 3 )–H lactonization reaction shown in Scheme 4 . The first step involves photolysis of TBN to form NO, which is then oxidized to NO 2 by oxygen.…”

Section: Table 1 Optimization Of the Synthesis Of Compo...mentioning

confidence: 55%

Visible-Light-Mediated Intramolecular Lactonization of Benzylic C(sp3)–H Bonds Promoted by DDQ and tert-Butyl Nitrite

Li,

Shen

et al. 2023

Synlett

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Functionalization of the benzylic C(sp3)-H bond was established through a mild, metal-free intramolecular lactonization protocol in the presence of DDQ/TBN photocatalysis, allowing practical and low-cost access to a series of phthalide products in moderate to excellent yields. Compared to many existing methodologies, this visible-light-driven process exhibited excellent substrate scope and fascinating features consisting of water as the sole byproduct, abundant and green energy source, commercially available catalysts, and room temperature. Finally, detailed mech-anistic investigations clearly revealed the role of photocatalysts and molecular oxygen.

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Section: Table 1 Optimization Of the Synthesis Of Compo...mentioning

confidence: 55%

Visible-Light-Mediated Intramolecular Lactonization of Benzylic C(sp3)–H Bonds Promoted by DDQ and tert-Butyl Nitrite

Li,

Shen

et al. 2023

Synlett

Self Cite

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Merging New and Old Concepts: Tandem Oxidative Radical‐Polar Crossover Ritter Amidation via Multicomponent Photo‐ and Electrochemical Processes

Lepori,

Dey,

Pratley

et al. 2024

Eur J Org Chem

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Nitrogen‐containing drug molecules and pharmaceuticals are ubiquitous, rendering the construction of C–N bonds a crucial target in methodology development. The Ritter reaction is a well‐established method for accessing C–N bonds by generating amide functionality through the reaction of carbocations and nitriles. Since its discovery back in 1948, the Ritter reaction has progressively advanced towards milder and more sustainable conditions for carbocation generation. In this regard, notable contributions have been made by means of single electron transfer (SET) chemistry. Nowadays, photo‐ and electrochemistry are established methods of choice for the generation of reactive radical intermediates and their subsequent oxidation via radical‐polar crossover (RPC) mechanism. We review recent examples of tandem RPC and Ritter‐type protocols, demonstrating how photo‐ and electrochemical energies have been effectively harvested to expand the precursor pool for the Ritter reaction and also reimagine the process with novel mechanisms and additives.

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Ritter-Type Reaction

Zhang,

Chen,

Gan

2024

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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Visible-light-mediated aerobic Ritter-type C–H amination of diarylmethanes using DDQ/tert-butyl nitrite

Abstract: A metal-free photocatalytic Ritter-type C-H amination of unactivated sp3 carbons using molecualr oxygen as terminal oxidant has been developed. By employing a co-catalytic system of 3-dichloro-4,5-dicyano-1,4-benzoquinone (DDQ) and tert-butyl nitrite...

Cited by 8 publications

References 38 publications

Visible-Light-Mediated Intramolecular Lactonization of Benzylic C(sp3)–H Bonds Promoted by DDQ and tert-Butyl Nitrite

Visible-Light-Mediated Intramolecular Lactonization of Benzylic C(sp3)–H Bonds Promoted by DDQ and tert-Butyl Nitrite

Merging New and Old Concepts: Tandem Oxidative Radical‐Polar Crossover Ritter Amidation via Multicomponent Photo‐ and Electrochemical Processes

Ritter-Type Reaction

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