- Aryl acyl peroxides for visible-light induced decarboxylative arylation of quinoxalin-2(1: H)-ones under additive-, metal catalyst-, and external photosensitizer-free and ambient conditions
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Aryl radicals were generated for the first time from cheap and easily available aryl acyl peroxides in eco-friendly ethyl acetate under ambient conditions and visible-light illumination in the absence of any additive, metal catalyst, or external photosensitizer. The present arylation of quinoxalin-2(1H)-ones was chemo- and regioselective, and provided good access to various 3-arylquinoxalin-2(1H)-ones. This journal is
- Xie, Long-Yong,Peng, Sha,Yang, Li-Hua,Peng, Cun,Lin, Ying-Wu,Yu, Xianyong,Cao, Zhong,Peng, Yu-Yu,He, Wei-Min
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supporting information
p. 374 - 378
(2021/01/28)
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- External-oxidant-free amino-benzoyloxylation of unactivated alkenes of unsaturated ketoximes with: O -benzoylhydroxylamines
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A new copper-catalyzed two-component amino-benzoyloxylation of unactivated alkenes of unsaturated ketoximes with O-benzoylhydroxylamines as the benzoyloxy sources is developed. Chemoselectivity of this method toward amino-benzoyloxylation or oxy-benzoyloxylation of alkenyl ketoximes relies on the position of the tethered olefins, and provides an external-oxidant-free alkene difunctionalization route that directly utilizes O-benzoylhydroxylamines as the benzoyloxy radical precursors and internal oxidants for the divergent synthesis of cyclic nitrones and isoxazolines.
- Chen, Jiangfei,Zhu, Yan-Ping,Li, Jin-Heng,Wang, Qiu-An
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supporting information
p. 5215 - 5218
(2021/05/31)
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- An unprecedented cobalt-catalyzed selective aroylation of primary amines with aroyl peroxides
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A novel and facile cobalt-catalyzed selective aroylation of primary amines with aroyl peroxides was developed for the synthesis of aryl amides. It was unprecedented that C[sbnd]N bond formation product was selectively generated without the common N[sbnd]O bond formation product. Aroyl peroxides act as the sole aroylation reagent without additional base or oxidant. The reactions proceeded under mild conditions and showed broad substrates scope with a series of primary amines and aroyl peroxides.
- Li, Dong,Li, Jiale,Li, Juanjuan,Yuan, Songdong,Zhang, Qian
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supporting information
(2020/09/16)
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- Method for preparing aroyl peroxide
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The invention discloses a method for preparing an aroyl peroxide. Aryl formic acid is uses as a starting material, and the raw material is easy to get, and is of many types; products obtained by the method disclosed by the invention are of various types and are widely used; furthermore, the method disclosed by the invention has the advantages of mild reaction condition, high yield of the target product, less pollution, and simple reaction operation and post-treatment process, and is suitable for industrial production.
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Paragraph 0018
(2019/10/01)
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- Uncatalyzed, on water oxygenative cleavage of inert C-N bond with concomitant 8,7-amino shift in 8-aminoquinoline derivatives
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Oxygenative cleavage of an inert CAr-NH2 bond with concomitant 1,2 amine migration in 8-aminoquinoline derivatives is reported in water at room temperature. The reaction is highly atom- and step-economical as both C- and N-containing fragments of the C-N bond cleavage are incorporated into the target molecule and is effected without the need for N-oxide. The reaction is scalable to gram level, and the products are useful as electrophilic partners for coupling reactions, ligands in catalysis and bioactive compounds.
- Botla, Vinayak,Pilli, Navyasree,Malapaka, Chandrasekharam
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supporting information
p. 1735 - 1742
(2019/04/08)
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- Transition metal free oxygenation of 8-aminoquinoline amides in water
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The oxygenation of 8-aminoquinoline amides by benzoyl peroxide at the C5 position in water is developed in the absence of a transition metal catalyst, affording the desired products in moderate to good yields of up to 88%. Mechanism studies reveal that the reaction would involve a radical process.
- Yao, Xinghui,Weng, Xin,Wang, Kaixuan,Xiang, Haifeng,Zhou, Xiangge
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supporting information
p. 2472 - 2476
(2018/06/11)
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- Thermoinduced Free-Radical C-H Acyloxylation of Tertiary Enaminones: Catalyst-Free Synthesis of Acyloxyl Chromones and Enaminones
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In this paper, the direct acyloxylation of the α-C(sp2)-H bond in tertiary β-enaminones is accomplished under catalyst-free conditions and ambient temperature by using aroyl peroxides as coupling partners. By means of a thermoinduced free-radical pathway, the present method enables facile and efficient synthesis of both acyloxylated chromones and enaminones.
- Guo, Yanhui,Xiang, Yunfeng,Wei, Li,Wan, Jie-Ping
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supporting information
p. 3971 - 3974
(2018/07/15)
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- Iron(iii)-catalyzed chelation assisted remote C-H bond oxygenation of 8-amidoquinolines
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Iron catalyzed site selective and chelation assisted C-H functionalization in 8-amidoquinolines is achieved. The remote C5-benzoxylation with benzoyl peroxide produced a variety of potentially bioactive 8-arylcarboxamido-5-benzoyloxy quinoline derivatives. The efficiency of the reaction reflects from the wide substrate scope with electronic differentiation on carboxamide and acyl peroxide in addition to tolerance of halo-substitutions on either of the aryls. The reaction is additive, silver free and proceeds without the exclusion of air or moisture.
- Vinayak, Botla,Navyasree, Pilli,Chandrasekharam, Malapaka
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p. 9200 - 9208
(2017/11/14)
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- Convenient peripheral aroyloxylation reactions of porphyrins and chlorophyll-a-based chlorins with benzoyl peroxide
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A practical and efficient methodology for the formation of C-O bonds on the porphyrin/chlorin periphery was developed. The aroyloxy-substituted porphyrins and chlorins related to chlorophyll-a at the β- and meso-positions, respectively, were conveniently synthesized by the free radical substitution reaction with benzoyl peroxide and its homologs.
- Li, Jiazhu,Zhang, Peng,Yao, Nan-Nan,Zhao, Li-Li,Wang, Jin-Jun,Shim, Young Key
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p. 1086 - 1089
(2015/02/18)
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- Copper-catalyzed Csp3-O cross-coupling of unactivated alkyl halides with organic peroxides
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An efficient Cu-catalyzed Csp3-O coupling of peroxides with haloalkanes is described. High yields of products were achieved under mild conditions. Significantly, in addition to primary alkyl halides, secondary alkyl halogenated hydrocarbons could also be applied to this system. The new reaction system could tolerate a wide range of organic peroxides.
- Chen, Huan-Huan,Wang, Guang-Zu,Han, Jin,Xu, Meng-Yu,Zhao, Yong-Qiang,Xu, Hua-Jian
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p. 212 - 217
(2014/01/06)
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- Convenient peripheral aroyloxylation reactions of porphyrins and chlorophyll-a-based chlorins with benzoyl peroxide
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A practical and efficient methodology for the formation of C-O bonds on the porphyrin/chlorin periphery was developed. The aroyloxy-substituted porphyrins and chlorins related to chlorophyll-a at the β- and meso-positions, respectively, were conveniently synthesized by the free radical substitution reaction with benzoyl peroxide and its homologs.
- Li, Jiazhu,Zhang, Peng,Yao, Nan-Nan,Zhao, Li-Li,Wang, Jin-Jun,Shim, Young Key
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p. 1086 - 1089
(2014/02/14)
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- A highly efficient Pd-catalyzed decarboxylative ortho-arylation of amides with aryl acylperoxides
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An efficient Pd-catalyzed decarboxylative ortho-arylation of amides with aryl acylperoxides was developed. A variety of anilides reacted with aryl acylperoxides to afford the corresponding ortho-arylation products, and N-methoxyarylamides generated phenanthridinones. This journal is
- Li, Dengke,Xu, Ning,Zhang, Yicheng,Wang, Lei
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supporting information
p. 14862 - 14865
(2014/12/11)
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- Palladium(II)-catalyzed othro-C-H-benzoxylation of 2-arylpyridines by oxidative coupling with aryl acylperoxides
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A palladium(II)-catalyzed ortho-benzoxylation of 2-arylpyridines with aryl acylperoxides was developed. With pyridyl as directing group, the benzoxylation reaction exhibits remarkable regioselectivity and excellent functional group tolerance, providing the products in up to 87% yield.
- Sit, Wing-Nga,Chan, Chun-Wo,Yu, Wing-Yiu
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p. 4403 - 4418
(2013/05/22)
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- Preparation For Initiating Radical Reactions
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A preparation, comprising a mixture of dibenzoyl peroxides where the mixture of dibenzoyl peroxides contains 50 to 99.7 mole % of a symmetric dibenzoyl peroxide and 0.3 to 50 mole % asymmetric dibenzoyl peroxides, shows a reduced decomposition temperature of the peroxides compared to the symmetric dibenzoyl peroxide and is suitable for hot cross-linking silicone rubber. The preparation can be produced by reacting a mixture containing a first benzoyl chloride and a second benzoyl chloride that is different therefrom with hydrogen peroxide, wherein the mixture of benzoyl chlorides contains 70 to 99.7 mole % of the first benzoyl chloride and 0.3 to 30 mole % of the second benzoyl chloride.
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Page/Page column 3
(2011/11/13)
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- Palladium-catalyzed decarboxylative arylation of C-H bonds by aryl acylperoxides
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A Pd(OAc)2-catalyzed protocol for decarboxylative arylation of aromatic C-H bond was developed using aryl acylperoxides as inexpensive aryl sources. Substrates containing pyridyl, oxime, and oxazoline groups undergo effectively ortho-selective C-H arylation with excellent functional group tolerance. This arylation should begin by directing-group-assisted cyclopalladation, followed by the reaction of the palladacycle with aryl radicals generated in situ by thermal decomposition of the peroxides.
- Yu, Wing-Yiu,Sit, Wing Nga,Zhou, Zhongyuan,Chan, Albert S.-C.
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supporting information; experimental part
p. 3174 - 3177
(2009/11/30)
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