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C-H官能化
JOURNAL OF ORGANIC CHEMISTRY · 2017 · IF 4.849

Carbene-Catalyzed Indole 3-Methyl C(sp3)–H Bond Functionalization

Jian Cheng,Jun Sun,Jiekuan Yan,Song Yang,Pengcheng Zheng,Zhichao Jin,Yonggui Robin Chi

The metal-free catalytic functionalization of aromatic sp2-carbons and benzylic sp3-carbons remains challenging. Here we report a carbene-catalyzed functionalization of the 3-methyl sp3-carbon attached to 2-formyl-indoles. The reaction proceeds through an NHC-bound o-quinodimethane as the key intermediate generated from 2-formyl-3-methylindoles under oxidative conditions. Reactive ketones are found to be effective substrates to produce substituted hydropyrano[3,4-b]indoles in good to excellent yields.

研究领域: 有机化学 · 合成化学
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RSC Advances · 2016 ·Vol. 6 ·期 59 ·54377-54381 · IF 3.289

TBAI–HBr system mediated generation of various thioethers with benzenesulfonyl chlorides in PEG400

Dingyi Wang,Shengmei Guo,Rongxing Zhang,Sen Lin,Zhaohua Yan

An efficient procedure for the formation of C–S bonds via C–H functionalization was developed for the synthesis of aryl sulfides in good to excellent yields using TBAI–HBr system promoted direct sulfenylation of various compounds, such as phenols, pyrazolones, indoles and related heteroarenes. Low cost and widely available arylsulfonyl chlorides were used as the sulfur source to provide various sulfur-containing compounds. The characteristic of the present protocol is convenient, green, highly efficient with a wide-application and short reaction time.

研究领域: 有机化学 · 合成化学
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MOLECULES · 2024 ·Vol. 29 ·期 20 ·4815 · IF 4.2

Remote Sulfonylation of Anilines with Sodium Sulfifinates Using Biomass-Derived Copper Catalyst

Xiaoping Yan,Jinguo Wang,Chao Chen,Kai Zheng,Pengfei Zhang,Chao Shen

A biomass-based catalyst, CuxOy@CS-400, was employed as an excellent recyclable heterogeneous catalyst to realize the sulfonylation reaction of aniline derivatives with sodium sulfinates. Various substrates were compatible, giving the desired products moderate to good yields at room temperature. In addition, this heterogeneous copper catalyst was also easy to recover and was recyclable up to five times without considerably deteriorating in catalytic efficiency. Importantly, these sulfonylation products were readily converted to the corresponding 4-sulfonyl anilines via a hydrolysis step. The method offers a unique strategy for synthesizing arylsulfones and has the potential to create new possibilities for developing heterogeneous copper-catalyzed C-H functionalizations.

CAS / MDL: 9012-76-4
研究领域: 有机化学 · 催化化学
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SYNLETT · 2011 ·Vol. 2012 ·期 01 ·145-149 · IF 2.447

Silver-Catalyzed 2-Pyridyl Arylation of Pyridine N-Oxides with Arylboronic Acids at Room Temperature

Wenpeng Mai,Jinwei Yuan,Zhicheng Li,Gangchun Sun,Lingbo Qu

All articles of this category A novel direct arylation of pyridine N -oxideswith arylboronic acids through C-H functionalization hasbeen developed. This new reaction is performed at room temperatureusing catalytic silver(I) nitrate in the presence of potassium persulfateand give 2-pyridyl arylation derivatives of pyridine N -oxides.

研究领域: 有机化学 · 催化反应
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APPLIED CATALYSIS B-ENVIRONMENTAL · 2018 · IF 11.698

Construction of donor-acceptor type conjugated microporous polymers: A fascinating strategy for the development of efficient heterogeneous photocatalysts in organic synthesis

Yongfeng Zhi,Si Ma,Hong Xia,Yumin Zhang,Zhan Shi,Ying Mu,Xiaoming Liu

Metal-free, visible-light driven, solid organic photocatalysts provide a more green and environmentally friendly alternative to traditional metal-based photocatalysts. Donor-Acceepor (D-A) dyads possess a feature of easy to adjust the photoelectric properties, and enhance their photocatalytic performances. Here we report a fascinating strategy for screening excellent organic porous photocatalysts through oxidative coupling of single D -A based monomer, which has still an important advantage to ensure uniformity of polymer structure except for the inherent characteristics of D -A polymers. According to this strategy, three D -A typed conjugated microporous polymer (DA-CMP) photocatalysts consisting of alternating electron-rich (carbazole) and electron-deficient (benzene, 4,7-diphenyl-2,1,3-benzothiadiazole or anthraquinone) units have been synthesized, and their porosity and photoelectric properties including adsorption, emission, lifetime, optical bandgaps, energy levels and transient photocurrent response as well as photocatalytic activity, were conveniently tuned by selecting different D -A monomers with tunable electron-deficient moiety. These DA-CMPs were exploited as metal-free photocatalysts in the oxidative C-H functionalization reactions in the presence of visible-light and molecular oxygen. They showed excellent photocatalytic activity, extensive substrate adaptability and outstanding reusability, due to combining some key features like permanent porosity, outstanding stability and optoelectronic properties. In addition, the reaction mechanism for DA-CMP photocatalyzed C-H functionalization reactions under visible-light irradiation was investigated in detail. Moreover, to prove in depth the benefits of the heterogeneous photocatalysis, a continuous flow procedure has been conducted with an excellent yield.

研究领域: 材料科学 · 有机化学
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