Photocatalyst-free visible-light-promoted quinazolinone synthesis at room temperature utilizing aldehydes generated in situ via CC bond cleavage

Author(s):  
Zongbo Xie ◽  
Jin Lan ◽  
Liyuan Yan ◽  
Xuehua Chen ◽  
Qian Li ◽  
...  

This is the first report on a facile tandem route for synthesizing quinazolinones at room temperature from various aminobenzamides and in situ-generated aldehydes.

RSC Advances ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 4763-4771 ◽  
Author(s):  
Muhammad Bilal Hussain ◽  
Malik Saddam Khan ◽  
Herman Maloko Loussala ◽  
Muhammad Sohail Bashir

Cr(vi) reduction is performed by BiOCl0.8Br0.2 composite produced via a facile in situ synthetic process at room temperature while making use of PVP (Mw = 10 000).


2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Fang-Fang Tan ◽  
Xiao-Ya He ◽  
Wan-Fa Tian ◽  
Yang Li

AbstractCleavage of C–O bonds in lignin can afford the renewable aryl sources for fine chemicals. However, the high bond energies of these C–O bonds, especially the 4-O-5-type diaryl ether C–O bonds (~314 kJ/mol) make the cleavage very challenging. Here, we report visible-light photoredox-catalyzed C–O bond cleavage of diaryl ethers by an acidolysis with an aryl carboxylic acid and a following one-pot hydrolysis. Two molecules of phenols are obtained from one molecule of diaryl ether at room temperature. The aryl carboxylic acid used for the acidolysis can be recovered. The key to success of the acidolysis is merging visible-light photoredox catalysis using an acridinium photocatalyst and Lewis acid catalysis using Cu(TMHD)2. Preliminary mechanistic studies indicate that the catalytic cycle occurs via a rare selective electrophilic attack of the generated aryl carboxylic radical on the electron-rich aryl ring of the diphenyl ether. This transformation is applied to a gram-scale reaction and the model of 4-O-5 lignin linkages.


2016 ◽  
Vol 52 (79) ◽  
pp. 11756-11759 ◽  
Author(s):  
Ayyakkannu Ragupathi ◽  
Arunachalam Sagadevan ◽  
Chun-Cheng Lin ◽  
Jih-Ru Hwu ◽  
Kuo Chu Hwang

An efficient and eco-friendly approach to aerobic oxidative C–N coupling of 2-aminopyridine with terminal alkynes for preparation of biologically important pyridyl-amides via CC triple bond cleavage at room temperature.


2020 ◽  
Author(s):  
Fang-Fang Tan ◽  
Xiao-Ya He He ◽  
Wan-Fa Tian ◽  
Yang Li

Abstract We have developed visible-light photoredox-catalyzed C–O bond cleavage of diaryl ethers by an acidolysis with an aryl car-boxylic acid and a following one-pot hydrolysis. Two phenols are obtained from a diaryl ether at room temperature. The aryl carboxylic acid used for the acidolysis can be recovered. The key to success of the acidolysis is merging visible-light photore-dox catalysis with a new acridinium photocatalyst and Lewic acid catalysis with Cu(TMHD)2. Preliminary mechanistic studies indicate that the catalytic cycle occurs via a rare selective electrophilic attack of the generated aryl carboxylic radical on the electron-rich aryl ring of diphenyl ether. This transformation is applied to a gram-scale reaction and the model of 4-O-5 lignin linkages.


2021 ◽  
Author(s):  
Vaibhav Pramod Charpe ◽  
Ayyakkannu Ragupathi ◽  
Arunachalam Sagadevan ◽  
Kuo Chu Hwang

We have developed a visible light-induced photo-redox copper-catalyzed oxidative Csp2-H annulation (Friedel–Crafts-type cyclization) of amidines with terminal alkynes at room temperature to synthesize functionalized quinazolines. This is the first report...


Author(s):  
Qiuzhong Li ◽  
Caijie Wu ◽  
Ke Wang ◽  
Xiaoxiao Wang ◽  
Xun Chen ◽  
...  

A Au/TiO2-PD sample was prepared by the mild in situ photo-deposition method and follow by heat treatment. As compared to the Au/TiO2-DP prepared by deposition precipitation, this Au/TiO2-PD sample owned...


Synlett ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 2581-2586 ◽  
Author(s):  
Wen-Jun Zhou ◽  
Da-Gang Yu ◽  
Yong-Yuan Gui ◽  
Xiao-Wang Chen

The arylation of amide and urea C(sp3)–H bonds with aryl tosylates generated in situ from phenols has been realized at room temperature by combining visible-light-photoredox catalysis, hydrogen-atom-transfer catalysis, and nickel catalysis. This streamlined protocol permits rapid functionalization of phenols and direct transformation of α-amino C(sp3)–H bonds. The C(sp3)–H arylation products are obtained in high yields with good functional-group tolerance at low catalyst loadings.


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