Direct synthesis of hydrazones by visible light mediated aerobic oxidative cleavage of the CC bond

Ding, Ya; Li, Hao; Meng, Yunge; Zhang, Te; Li, Jiawen; Chen, Qiuyun; Zhu, Chunyin

doi:10.1039/c7qo00276a

Cited by 42 publications

(25 citation statements)

References 63 publications

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“…Zhu and co-workers in 2017 developed a photocatalytic method for the conversion of styrenes to aryl hydrazones in the presence of a hydrazine partner, proceeding through C=C bond cleavage ( Scheme 115 ). 346 Reaction conditions involved the blue-light irradiation of substrate solutions in MeCN, in the presence of [ MB ]Cl photocatalyst and 2,6-lutidine Brønsted base additive, under an air atmosphere. In total, 24 examples of this oxidative C=C bond cleavage reaction were reported in 52–78% yields.…”

Section: N -Centered Radical Generation From N–h Bonds Through Photochemical and Electrochemical Pcet Processesmentioning

confidence: 99%

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

et al. 2021

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We present here a review of the photochemical and electrochemical applications of multi-site proton-coupled electron transfer (MS-PCET) in organic synthesis. MS-PCETs are redox mechanisms in which both an electron and a proton are exchanged together, often in a concerted elementary step. As such, MS-PCET can function as a non-classical mechanism for homolytic bond activation, providing opportunities to generate synthetically useful free radical intermediates directly from a wide variety of common organic functional groups. We present an introduction to MS-PCET and a practitioner’s guide to reaction design, with an emphasis on the unique energetic and selectivity features that are characteristic of this reaction class. We then present chapters on oxidative N–H, O–H, S–H, and C–H bond homolysis methods, for the generation of the corresponding neutral radical species. Then, chapters for reductive PCET activations involving carbonyl, imine, other X=Y π-systems, and heteroarenes, where neutral ketyl, α-amino, and heteroarene-derived radicals can be generated. Finally, we present chapters on the applications of MS-PCET in asymmetric catalysis and in materials and device applications. Within each chapter, we subdivide by the functional group undergoing homolysis, and thereafter by the type of transformation being promoted. Methods published prior to the end of December 2020 are presented.

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Section: N -Centered Radical Generation From N–h Bonds Through Photochemical and Electrochemical Pcet Processesmentioning

confidence: 99%

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

et al. 2021

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“…This intriguing result led us to consider whether these byproducts were arising from an unusual oxidative cleavage of the olefin directly to an N-tosyl imine. 13 If this were the case, one would expect to also observe the formimine as a second product, which we did not. However, if this product were formed in trace amounts, subsequent consumption under the reaction conditions or workup (due to increased electrophilicity compared to 34) might prevent detection.…”

Section: ■ Results and Discussionmentioning

confidence: 60%

“…In particular, for all successful reactions disclosed in Table , a small amount of an imine byproduct (e.g., 34 ) could be observed and quantified by 1 H NMR of the crude reaction mixture (Scheme a). This intriguing result led us to consider whether these byproducts were arising from an unusual oxidative cleavage of the olefin directly to an N -tosyl imine . If this were the case, one would expect to also observe the formimine as a second product, which we did not.…”

Section: Resultsmentioning

confidence: 73%

Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight

Johnson

Hilinski

2019

J. Org. Chem.

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Olefin aziridination via organocatalytic nitrene transfer offers potential complementarity to metalcatalyzed methods, however there is a lack of reports of such reactions in the literature. Herein is reported a method that employs an iminium salt to catalyze the aziridination of styrenes by [N-(ptoluenesulfonyl)imino]phenyliodinane (PhINTs). These reactions are hypothesized to proceed via a diaziridinium salt as the active oxidant. In addition to outlining the scope and limitations of the method, evidence for a polar, stepwise mechanism is presented, which provides new insight into the nature of iminium catalysis of nitrene transfer.

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“…In general, the strategy in this study consisted of replacing the indole ring with the bioisosteric naphthalene ring. All twenty-one compounds except 1h (Robev, 1981), 1r (Robev, 1968) and 1u (Weil, Ostermeier, 1921;Ding et al, 2017) were new. Furthermore, the compounds 1n, 1p and 1o have CAS registry numbers, but there is no information in the literature related to the biological activity of these.…”

Section: Introductionmentioning

confidence: 98%

Bioisosteric modification on melatonin: synthesis of new naphthalene derivatives, in vitro antioxidant activity and cytotoxicity studies

Shirinzadeh

Ghalia

Tascioglu

et al. 2020

Braz. J. Pharm. Sci.

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Melatonin (MLT) is a strong free radical scavenger that protects the body from the deleterious effects of excess oxidants. Synthesis of MLT analogue compounds with antioxidant potency has recently attracted the interest of researchers. In general, the strategy consists of modifying the groups in the different sites of the indole ring or replacing the indole ring with an analogue. As part of our ongoing research, the antioxidant capacity and cytotoxicity of newly synthesized MLT analogue naphthalene derivatives were evaluated. The radical scavenging activity was tested by a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Most of the synthesized compounds showed significant antioxidant activity in comparison to MLT. The structure-activity relationship was identified. The in vitro cytotoxic effects of the synthesized compounds were also investigated in CHO-K1 cells using the MTT assay.

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Direct synthesis of hydrazones by visible light mediated aerobic oxidative cleavage of the CC bond

Abstract: A metal-free protocol through visible light mediated oxidative cleavage of CC bonds to directly construct CN bonds has been developed for the conversion of alkenes to hydrazones under mild conditions.

Cited by 42 publications

References 63 publications

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight

Bioisosteric modification on melatonin: synthesis of new naphthalene derivatives, in vitro antioxidant activity and cytotoxicity studies

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