Palladium-catalyzed direct ortho-sulfonylation of azobenzenes with arylsulfonyl chlorides via C–H activation

Xia, Chengcai; Wei, Zhenjiang; Shen, Chao; Yang, Yong; Su, Weike; Zhang, Pengfei

doi:10.1039/c5ra06474k

Cited by 35 publications

(9 citation statements)

References 56 publications

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“…On the basis of the above results and previous reports, , we proposed a possible reaction mechanism (Scheme ). Initially, enamine A is formed by the N -aminomorpholine ([NH]H) and AcOH catalysts.…”

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confidence: 62%

Selective Mono- and Diamination of Ketones in a Combined Copper–Organocatalyst System

et al. 2022

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Herein, we report a simple and mild protocol for the chemoselective mono- and diamination of ketone using pyrazole as the amine source in a combined copper–organocatalyst system. Various substrates are compatible, providing the corresponding products in moderate to good yields. This strategy gives an efficient and convenient solution for the synthesis of α-pyrazole and α,α-dipyrazole ketone derivatives. The control experiment demonstrates that in situ generated hydrazone is a key intermediate in the transformation.

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confidence: 62%

Selective Mono- and Diamination of Ketones in a Combined Copper–Organocatalyst System

et al. 2022

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“…The success of the C–H activation strategy prompted the groups of Zhang and Wu to explore the C sp 2 –S bond formation starting from azobenzene derivatives (Scheme ). They reported two different Pd-catalyzed systems using similarly arylsulfonyl chlorides 25 as sulfonylation agents for the selective synthesis of sulfonylated azos 26 . If the scope studies of the both approaches revealed similar trends such as a good substituants tolerance for the arylsulfonyl derivatives, a better reactivity of electron-enriched azobenzenes and a lack of site-selectivity for unsymmetrical azos, the main difference lied in the speculated mechanism.…”

Section: Monofunctionalization Of Azobenzenesmentioning

confidence: 99%

Advances in Direct Metal-Catalyzed Functionalization of Azobenzenes

2018

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Azobenzenes are a unique class of compounds that originally aroused interest because of their exceptional photochromic properties. Selective reactions allowing the preparation of complex polysubstituted azo-based photoswitches, in a direct and efficient manner, have received considerable attention over the past few years. Among them, regio- and chemoselective C–H bond activation in the presence of a transition-metal catalyst has emerged as the most attractive and challenging strategy in the synthesis of sterically constrained azo compounds. This synthetic approach is currently an intensive research field for introducing functional and structural diversity from azobenzenes. This short review summarizes the recent advances in both ortho-functionalization of azobenzenes and the synthesis of azo-derived heterocycles based on transition-metal-catalyzed direct C–H bond activation. The substrate scope, limitation, reaction mechanism as well as additional applications are discussed.

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“…Our research group has been engaged in the research of azo compounds. [13][14][15][16] Herein, we report a method for the synthesis of (E)-1-(phenyldiazenyl)cyclohexyl benzoate, which can synthesize azo compounds in high yield by arylhydrazine oxidation (Scheme 1B).…”

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confidence: 99%

Synthesis of (E)‐1‐(phenyldiazenyl)cyclohexyl Benzoate from N‐(cyclohexylideneamino)aniline and Benzoyl Peroxide

Zhu

Chen

et al. 2022

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Palladium-catalyzed direct ortho-sulfonylation of azobenzenes with arylsulfonyl chlorides via C–H activation

Abstract: Ortho-sulfonylated azobenzenes were obtained in moderate to high yields by direct ortho-sulfonylation of azobenzenes C-H bond with arylsulfonyl chlorides.

Cited by 35 publications

References 56 publications

Selective Mono- and Diamination of Ketones in a Combined Copper–Organocatalyst System

Selective Mono- and Diamination of Ketones in a Combined Copper–Organocatalyst System

Advances in Direct Metal-Catalyzed Functionalization of Azobenzenes

Synthesis of (E)‐1‐(phenyldiazenyl)cyclohexyl Benzoate from N‐(cyclohexylideneamino)aniline and Benzoyl Peroxide

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