Se-mediated one-pot synthesis of 2-substituted benzoselenazole derivatives from 2 to iodoanilines and arylacetic acids/arylmethyl chlorides

Gu, Ren; Wang, Xin; Zhao, Yang; Han, Shiqing

doi:10.1016/j.tetlet.2018.06.027

Cited by 22 publications

(17 citation statements)

References 34 publications

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“…We notice that by far no radical-initiated cascade reaction concerning starting from 4a to the related 2-substituted benzoselenazoles has been reported. Comparably, only several 2-substituted benzoselenazoles, including 2-NH 2 , 2-R (alkyl/phenyl), 2-OR, or 2-SR substituted benzoselenazoles have been synthesized via commonly used condensation and cyclization methods . Thus, this newly developed perfuoroalkyl radical initiated cascade reaction provides, for the first time, a feasible way to access biologically potential 2-perfluoroalkylbenzoselenazoles, starting from structurally simple (2-isocyanophenyl)(methyl)selane and easily available perfluoroalkyl iodides.…”

mentioning

confidence: 99%

Visible-Light Induced Radical Perfluoroalkylation/Cyclization Strategy To Access 2-Perfluoroalkylbenzothiazoles/Benzoselenazoles by EDA Complex

et al. 2019

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A novel and practical fluoroalkyl radical-initiated cascade reaction was developed to access diverse 2-fluoroalkylbenzothiazoles by reacting various fluoroalkyl radical sources, including perfluoroalkyl iodide (IC n F2n+1, n = 3–8, 10), ICF(CF3)2, ICF2COOEt, ICF2CF2Cl, or ICF2CF2Br, tetramethylethane-1,2-diamine (TMEDA), and 2-isocyanoaryl thioethers in tetrahydrofuran under nitrogen atmosphere and blue-light irradiation conditions. Furthermore, this one-pot protocol could well be expanded to access various 2-fluoroalkylbenzoselenazoles starting from (2-isocyanophenyl)(methyl)selane, perfluoroalkyl iodides (IC n F2n+1, n = 3–8) or ICF2COOEt and TMEDA.

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mentioning

confidence: 99%

Visible-Light Induced Radical Perfluoroalkylation/Cyclization Strategy To Access 2-Perfluoroalkylbenzothiazoles/Benzoselenazoles by EDA Complex

et al. 2019

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“…Common synthetic methods include the use of bis(2‐aminophenyl)diselenides or 2‐iodoanilines as substrates under transition‐metal‐catalyzed or oxidative conditions . Benzyl halides have been used widely to prepare benzazoles these years in that they are active and easily available, however, literature employing it as a substrate to synthesize benzoselenazole is still rare . We reported the synthesis of benzoxazoles from nitrophenol and arylmethyl chloride/arylacetic acid as substrates under metal‐free conditions previously (Scheme , eq.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 2‐Arylbenzoselenazoles from Se‐mediated Redox Condensation of 2‐Chloronitrobenzene and Arylmethyl Chloride

Gan

Cao

2020

ChemistrySelect

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A selenium-mediated redox condensation of 2-chloronitrobenzene and arylmethyl chloride to obtain 2-arylbenzoselenazoles has been realized under metal-free condition. The reactions proceeded in moderate-to-good yields with good functional compatibility and gram-scale achievement. Primarily mechanistic investigation suggested that key intermediate Bn(Se)nBn II, was first isolated and confirmed by NMR.

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“…Recently, another three‐component reaction of 2‐iodoanilines, selenium powder, arylacetic acids or benzyl chlorides was developed for the preparation of benzoselenazoles (Scheme 31). [64] The reaction was carried out under ligand‐free and additive‐free conditions. The authors found that the employment of DMSO as the solvent was crucial to the reaction outcomes of the desired products.…”

Section: Synthesis Of Organoselenium Compounds With Elemental Seleniummentioning

confidence: 99%

Synthesis of Organoselenium Compounds with Elemental Selenium

Liu

Zhou

et al. 2021

Adv Synth Catal

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In the recent decade, growing efforts have been devoted to employing elemental selenium as a selenium source in organic synthesis. In contrast to unstable, smelly, and toxic previous selenium reagents, elemental selenium is readily available, cheap, bench-stable, and easy to handle. This review will mainly focus on the strategies for the activation of elemental selenium and the synthesis of organoselenium compounds including monoselenides, diselenides, selenium-containing heterocycles and so on. The Synthesis ofMonoselenides with Elemental Selenium 2.2. The Synthesis of Diselenides with Elemental Selenium 2.3. The Synthesis of Selenium-Containing Heterocycles with Elemental Selenium 2.4. The Synthesis of Other Organoselenium Compounds with Elemental Selenium 3. Conclusions

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Se-mediated one-pot synthesis of 2-substituted benzoselenazole derivatives from 2 to iodoanilines and arylacetic acids/arylmethyl chlorides

Cited by 22 publications

References 34 publications

Visible-Light Induced Radical Perfluoroalkylation/Cyclization Strategy To Access 2-Perfluoroalkylbenzothiazoles/Benzoselenazoles by EDA Complex

Visible-Light Induced Radical Perfluoroalkylation/Cyclization Strategy To Access 2-Perfluoroalkylbenzothiazoles/Benzoselenazoles by EDA Complex

Synthesis of 2‐Arylbenzoselenazoles from Se‐mediated Redox Condensation of 2‐Chloronitrobenzene and Arylmethyl Chloride

Synthesis of Organoselenium Compounds with Elemental Selenium

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