- Ruthenium-Catalyzed C-H Bond Activation Approach to Azolyl Aminals and Hemiaminal Ethers, Mechanistic Evaluations, and Isomer Interconversion
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C(sp3)-N bond-forming reactions between benzotriazole and 5,6-dimethylbenzotriazole with N-methylpyrrolidinone, tetrahydrofuran, tetrahydropyran, diethyl ether, 1,4-dioxane, and isochroman have been conducted using RuCl3·3H2/su
- Singh, Manish K.,Akula, Hari K.,Satishkumar, Sakilam,Stahl, Lothar,Lakshman, Mahesh K.
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- Cross-dehydrogenative coupling of azoles with α-c(sp3)-h of ethers and thioethers under metal-free conditions: Functionalization of h-n azoles via c-h activation
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A metal-free cross-dehydrogenative coupling method for the synthesis of N-substituted azoles has been developed. The TBAI/TBHP system catalyzed the coupling of azoles with ethers and thioethers via α-C(sp3)-H activation. Under the optimized conditions, a diverse range of un/substituted azoles such as 1H-benzimidazole, 9H-purine, 1H-benzotriazole, 1H-1,2,3-triazole, 1H-1,2,4-triazole, and 1H-pyrazole were successfully employed for coupling with various ethers and thioethers such as tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethyl ether, tetrahydrothiophene, and 1,3-dithiolane.
- Aruri, Hariprasad,Singh, Umed,Sharma, Sumit,Gudup, Satish,Bhogal, Mukesh,Kumar, Sanjay,Singh, Deepika,Gupta, Vivek K.,Kant, Rajni,Vishwakarma, Ram A.,Singh, Parvinder Pal
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- Synthesis of novel 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolines via benzotriazole methodology
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Pyrroloquinolines have been synthesized reacting 1-(benzotriazol-1(2)-ylmethyl)indolines with unactivated and electron-rich alkenes in the presence of p-toluenesulfonic acid catalyst. Mixtures of the expected diastereomers were obtained and some of them s
- Abonia, Rodrigo,Albornoz, Andrea,Insuasty, Braulio,Quiroga, Jairo,Meier, Herbert,Hormaza, Angelina,Nogueras, Manuel,Sánchez, Adolfo,Cobo, Justo,Low, John N
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- Dibenzo[b,h][1,4,7]thiadiazonines: Examples of a novel ring system
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Acetanilides la-e react with 1,1′-sulfinylbis(benzotriazole)/trimethylchlorosilane at 45-65 °C to form 1,2-di(benzotriazol-1-yl)-2-arylimino-l-ethanethiones 3a-e, while heating the same reagents at 110 °C results in dibenzo[b, h][1,4,7]thiadiazonines 5a,c,d, and 6. X-ray crystal structures are reported for three representative examples.
- Katritzky,Huang,Steel
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- Decatungstate-Mediated C(sp3)–H Heteroarylation via Radical-Polar Crossover in Batch and Flow
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Photocatalytic hydrogen atom transfer is a very powerful strategy for the regioselective C(sp3)–H functionalization of organic molecules. Herein, we report on the unprecedented combination of decatungstate hydrogen atom transfer photocatalysis with the oxidative radical–polar crossover concept to access the direct net-oxidative C(sp3)–H heteroarylation. The present methodology demonstrates a high functional group tolerance (40 examples) and is scalable when using continuous-flow reactor technology. The developed protocol is also amenable to the late-stage functionalization of biologically relevant molecules such as stanozolol, (?)-ambroxide, podophyllotoxin, and dideoxyribose.
- Capaldo, Luca,Frederick, Michael O.,García-Losada, Pablo,Laudadio, Gabriele,Mateos, Carlos,No?l, Timothy,Nu?o, Manuel,Nyuchev, Alexander V.,Rincón, Juan A.,Wan, Ting
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supporting information
p. 17893 - 17897
(2021/07/14)
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- Organocatalytic amination of alkyl ethers via n-Bu4NI/t-BuOOH-mediated intermolecular oxidative C(sp3)-N bond formation: Novel synthesis of hemiaminal ethers
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A novel method for constructing the hemiaminal ether framework under metal-free conditions has been developed. It involves direct organocatalytic amination of alkyl ethers through intermolecular oxidative C(sp3)-N bond formation, with t-BuOOH being the oxidant and n-Bu4NI as the catalyst.
- Dian, Longyang,Wang, Sisi,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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supporting information
p. 11738 - 11741
(2015/05/20)
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