28988-01-4Relevant academic research and scientific papers
UiO-66 microcrystals catalyzed direct arylation of enol acetates and heteroarenes with aryl diazonium salts in water
Sun, Zhong-Hua,Chen, Wang,Qian, Bing-Bing,Wang, Liang,Yu, Binxun,Chen, Qun,He, Ming-Yang,Zhang, Zhi-Hui
, (2020/01/25)
UiO-66 is a classic Metal–organic framework (MOF) that constructed by zirconium cations and terephthalate with high chemical and thermal stability. Using pristine UiO-66 nanocrystals as the catalysts, the carbon–carbon bond formation based on denitrogenat
Black phosphorus as a metal-free, visible-light-active heterogeneous photoredox catalyst for the direct C-H arylation of heteroarenes
Kalay, Erbay,Kü?ükke?eci, Hüseyin,Kilic, Haydar,Metin, ?nder
supporting information, p. 5901 - 5904 (2020/06/04)
Black phosphorus (BP) is for the first time employed as a metal-free, heterogeneous photoredox catalyst for the direct C-H arylation of heteroarenes with aryl diazonium salts. The arylated heteroarenes are obtained in moderate to good yields under visible-light illumination, and the protocol is shown to be applicable for the scale-up synthesis.
Perylenequinonoid-catalyzed photoredox activation for the direct arylation of (het)arenes with sunlight
Zhang, Shiwei,Tang, Zhaocheng,Bao, Wenhao,Li, Jia,Guo, Baodang,Huang, Shuping,Zhang, Yan,Rao, Yijian
supporting information, p. 4364 - 4369 (2019/05/10)
Naturally occurring perylenequinonoid pigments (PQPs) have attracted considerable attention owing to their excellent properties of photosensitization. They have been widely investigated as an aspect of photophysics and photobiology. However, their applications in photocatalysis are yet to be explored. We report here that sunlight along with 1 mol% cercosporin, which is one of the perylenequinonoid pigments, catalyzes the direct C-H bond arylation of (het)arenes by a photoredox process with good regioselectivity and broad functional group compatibility. Furthermore, a gram-scale reaction with great conversions of substrates was achieved even by a cercosporin-containing supernatant without organic solvent extraction and purification after liquid fermentation. Thus we set up a bridge between microbial fermentation and organic photocatalysis for chemical reactions in a sustainable, environmentally friendly manner.
Redox reactions of small organic molecules using ball milling and piezoelectric materials
Kubota, Koji,Pang, Yadong,Miura, Akira,Ito, Hajime
, p. 1500 - 1504 (2020/01/08)
Over the past decade, photoredox catalysis has harnessed light energy to accelerate bond-forming reactions. We postulated that a complementary method for the redox-activation of small organic molecules in response to applied mechanical energy could be dev
Continuous Visible-Light Photoflow Approach for a Manganese-Catalyzed (Het)Arene C?H Arylation
Liang, Yu-Feng,Steinbock, Ralf,Yang, Long,Ackermann, Lutz
supporting information, p. 10625 - 10629 (2018/08/01)
Manganese photocatalysts enabled versatile room-temperature C?H arylation reactions by means of continuous visible-light photoflow, thus allowing for efficient C?H arylations in 30 minutes with ample scope. The robustness of the manganese-catalyzed photoflow strategy was shown by visible light-induced gram-scale synthesis, clearly outperforming the batch performance.
C-H arylation reactions through aniline activation catalysed by a PANI-g-C3N4-TiO2 composite under visible light in aqueous medium
Wang, Liang,Shen, Jun,Yang, Sen,Liu, Wenjie,Chen, Qun,He, Mingyang
supporting information, p. 1290 - 1296 (2018/03/26)
A PANI (polyaniline)-g-C3N4-TiO2 composite was prepared and found to be efficient for radical C-H arylation reactions. The arylation process involved coupling of in situ generated aryl diazonium salts from aniline with heteroarenes, enol acetates or benzoquinones under visible light in aqueous medium or pure water. A broad range of substrates survived the reaction conditions to provide the desired products in moderate to good yields. Scale-up (10 mmol) synthesis was also achieved. This semiconductor photocatalyst showed good photocatalytic performance and stability. Recycle studies showed that this composite could be readily recovered and a slight decrease in the catalytic activity was observed after ten consecutive runs.
Merging visible-light photoredox and micellar catalysis: Arylation reactions with anilines nitrosated in situ
Bu, Mei-Jie,Lu, Guo-Ping,Jiang, Jianzhong,Cai, Chun
, p. 3728 - 3732 (2018/08/12)
An aqueous photocatalytic system was designed by merging visible-light photoredox catalysis with micellar catalysis. Eosin B, an organic dye, was utilized as the photocatalyst, and Triton X-100 was employed as the surfactant; both are inexpensive and commercially available. This clean and energy-saving catalytic system enables photocatalytic reactions of the diazonium ion generated in situ to proceed smoothly in water without any co-solvents or additives at room temperature.
Mild-Base-Promoted Arylation of (Hetero)Arenes with Anilines
Monzón, Diego M.,Santos, Tanausú,Pinacho-Crisóstomo,Martín, Víctor S.,Carrillo, Romen
supporting information, p. 325 - 333 (2018/01/15)
Transition metal-free radical arylation of heteroarenes is achieved at room temperature by simply adding aqueous sodium carbonate to a solution of the corresponding heteroarene and arenediazonium salt, which can even be formed in situ. Such an easy, inexpensive and mild methodology has been optimized and applied to the expeditious modification of interesting molecular cores like naphthylimide or bisthienylcyclopentenes.
One-Pot Preparation of Stable Organoboronate Reagents for the Functionalization of Unsaturated Four- and Five-Membered Carbo and Heterocycles
Baumann, Andreas N.,Eisold, Michael,Music, Arif,Didier, Dorian
, p. 3149 - 3160 (2018/05/28)
Combining a facile preparation of organoboronates with their remarkable stability and functional group tolerance allows for the straightforward synthesis of four- and five-membered carbo- and heterocycles. While most strategies rely on the ex situ preparation of boronic acids as isolated intermediates, we demonstrate that in situ transmetalation of sensitive organometallics with boron alkoxides can lead to great stabilization of such species at room temperature. A considerable extension of the library of unsaturated strained structures is achieved through these sequences, expanding the potential applicability of such unusual building blocks.
An Active Palladium Colloidal Catalyst for the Selective Oxidative Heterocoupling of (Hetero)Aryl Boronic Acids
Sable, Vaibhav,Maindan, Karan,Bhilare, Shatrughn,Chrysochos, Nicolas,Schulzke, Carola,Kapdi, Anant R.
supporting information, p. 2489 - 2498 (2018/09/10)
A highly selective oxidative heterocoupling protocol for (hetero)aryl boronic acids with an active palladium colloidal catalyst was developed. The judicious choice of electronically different aryl boronic acids made possible such couplings under mild conditions, with air as oxidant, while embracing a wide substrate scope. This successful approach further allowed the development of a unique one-pot sequential oxidative heterocoupling/Suzuki–Miyaura cross-coupling tandem process for accessing substituted terphenyls.
