Catalytic Intermolecular Haloamidation of Simple Alkenes with <i>N</i>-Halophthalimide as Both Nitrogen and Halogen Source

Lu, Song; Luo, Sanzhong; Cheng, Jiang

doi:10.1021/ol402726d

Cited by 35 publications

(17 citation statements)

References 42 publications

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“…The reaction did not proceed without blue-LED irradiation, which excludes the possibility of a bromonium-mediated haloimidation. 8 At present, we think that 5a and 5b can directly absorb blue light to homolytically cleave the N–Br bond. 9 The product yield depends on the pressure of ethylene gas, i.e., higher pressure (10 atm) increased the yield to 85%.…”

Section: Results and Discussionmentioning

confidence: 97%

Radical Difunctionalization of Gaseous Ethylene Guided by Quantum Chemical Calculations: Selective Incorporation of Two Molecules of Ethylene

et al. 2021

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Ethylene, of which about 170 million tons are produced annually worldwide, is a fundamental C 2 feedstock that is widely used on an industrial scale for the synthesis of polyethylenes and polyvinylchlorides. Compared to other alkenes, however, the direct use of ethylene for the synthesis of fine chemicals such as pharmaceuticals and agrochemicals is limited, probably due to its small and gaseous character. We, herein, report a new radical difunctionalization strategy of ethylene, aided by quantum chemical calculations. Computationally proposed imidyl and sulfonyl radicals can be introduced into ethylene in the presence of an Ir photocatalyst under irradiation with blue light-emitting diodes (LEDs) (λ max = 440 nm). The present reaction systems led to the selective incorporation of two molecules of ethylene into the substrate, which could be rationally explained by computational analysis.

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Section: Results and Discussionmentioning

confidence: 97%

Radical Difunctionalization of Gaseous Ethylene Guided by Quantum Chemical Calculations: Selective Incorporation of Two Molecules of Ethylene

et al. 2021

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“…Next, we investigated the difunctionalization strategy (Scheme , route 3). With the goal of generating intermediate 4 by means of a one-step aminohalogenation reaction − between 4-chloromethylstyrene ( 14 ) and 2,6-difluorobenzamide, we tested various halogenation agents (NBS, N -iodosuccinimide, Br 2 , I 2 , BBr 3 , and 1,3-dichloro-5,5-dimethylhydantoin) and several Lewis acid catalysts (FeCl 2, CuI, CuCl, Cu(OAc) 2 , and Cu 2 O) (Scheme , route a). However, extensive screening of reaction conditions failed to afford an isolated yield higher than 15%.…”

Section: Resultsmentioning

confidence: 99%

Route Evaluation and Ritter Reaction Based Synthesis of Oxazoline Acaricide Candidates FET-II-L and NK-12

Chen

Liu

Wang

2020

Org. Process Res. Dev.

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Clean synthetic processes are essential for industrial production of bioactive molecules. In this study, we explored several routes for the synthesis of acaricide candidates FET-II-L and NK-12 with the goal of developing a rapid route that is suitable for industrial production. Our results led us to adopt a Ritter reaction based aminohalogenation strategy that features fewer steps, simpler operation, and greatly increased overall yields relative to those of previously reported syntheses. After further optimization, the route reported herein is likely to be applicable for large scale production of these molecules.

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“…4aa-4ag underwent palladium-catalyzed intracellular C-N formation to accomplish the indole ring construction in series 1 compounds (5a-5g) ( Bugaenko et al., 2018 ; Ignatenko et al., 2010 ). Meanwhile, the terminal vinyl double bond in 4aa could be used as an acceptor for halogenation ( Meimetis et al., 2014 ; Song et al., 2013 ). Then, NBS was utilized to assemble 2-substituted 3-quaternary carbon-centered indole 6 that is not easily prepared via conventional methods (series 2) ( Golubev and Krasavin, 2017 ).…”

Section: Resultsmentioning

confidence: 99%

Highly Reactive Cyclic Monoaryl Iodoniums Tuned as Carbene Generators Couple with Nucleophiles under Metal-Free Conditions

et al. 2020

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Summary Cross-coupling reactions between aryl iodide and nucleophiles have been well developed. Iodoniums equipped with a reactive C-I(III) bond accelerate cross-coupling reactions of aryl iodide. Among them, cyclic diaryliodoniums are more atom economical; however; they are often in the trap of metal reliance and encounter regioselectivity issues. Now, we have developed a series of highly reactive cyclic monoaryl-vinyl iodoniums that can be tuned to construct C-N, C-O, and C-C bonds without metal catalysis. Under promotion of triethylamine, coupling reactions with aniline, phenol, aromatic acid, and indole proceed rapidly and regioselectively at room temperature. The carbene species is conceptualized as a key intermediate in our mechanism model. Furthermore, the coupling products enable diversity-oriented synthesis strategy to further build up a chemical library of diverse heterocyclic fragments that are in demand in the drug discovery field. Our current work provides a deep insight into the synthetic application of these highly reactive cyclic iodoniums.

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Catalytic Intermolecular Haloamidation of Simple Alkenes with N-Halophthalimide as Both Nitrogen and Halogen Source

Cited by 35 publications

References 42 publications

Radical Difunctionalization of Gaseous Ethylene Guided by Quantum Chemical Calculations: Selective Incorporation of Two Molecules of Ethylene

Radical Difunctionalization of Gaseous Ethylene Guided by Quantum Chemical Calculations: Selective Incorporation of Two Molecules of Ethylene

Route Evaluation and Ritter Reaction Based Synthesis of Oxazoline Acaricide Candidates FET-II-L and NK-12

Highly Reactive Cyclic Monoaryl Iodoniums Tuned as Carbene Generators Couple with Nucleophiles under Metal-Free Conditions

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