Synthesis of N-Sulfonyl- and N-Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction

Synthesis ◽  
2019 ◽  
Vol 51 (19) ◽  
pp. 3651-3666
Author(s):  
Weiqiang Chen ◽  
Yin-Lin Zhang ◽  
Hui-Jing Li ◽  
Xiang Nan ◽  
Ying Liu ◽  
...  

N-Sulfonyl- and N-acylpyrroles were synthesized via olefin ring-closing metathesis of diallylamines and in situ oxidative aromatization in the presence of the ruthenium Grubbs catalyst and a suitable copper catalyst. In the presence of Cu(OTf)2 and CuBr2, the reaction afforded N-sulfonyl- and N-acylpyrroles, respectively, in one pot. Under an oxygen atmosphere, the reaction went smoothly without the need of hydroperoxide oxidants. This protocol possesses many advantages, such as using a nonhazardous oxidant and readily available starting materials, operating in one pot, and showing a broad substrate scope.

2014 ◽  
Vol 170 ◽  
pp. 1-5 ◽  
Author(s):  
Zong-Bo Xie ◽  
Na Wang ◽  
Wan-Xia Wu ◽  
Zhang-Gao Le ◽  
Xiao-Qi Yu

2021 ◽  
Vol 8 ◽  
Author(s):  
Fa-Jie Chen ◽  
Zhenguo Hua ◽  
Jianhui Chen ◽  
Jiajia Chen ◽  
Daesung Lee ◽  
...  

Herein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and terminal alkynes at room temperature, which are directly converted to (Z)-β-halovinyl ketones by treating with triflic acid. This method avoids the use of an external halogen source and features broad substrate scope, high yield, and good to excellent stereoselectivity.


Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 2043 ◽  
Author(s):  
Mariusz Kędziorek ◽  
Liliana Dobrzańska

Promising results of an efficient and convenient strategy for the annulation of polycyclic aromatic compounds (PACs), employing orthoquinones as starting material and comprising allylation, pinacol rearrangement, ring-closing metathesis (RCM), and one-pot reduction followed by Wagner-Meerwein rearrangement, are presented. The strategy involves introducing triallylborane prepared in situ in the allylation step. Moreover, a novel expedient method for the preparation of 9,10-diallylphenanthrene was introduced.


2014 ◽  
Vol 50 (95) ◽  
pp. 14968-14970 ◽  
Author(s):  
Yan He ◽  
Xinying Zhang ◽  
Xuesen Fan

A one-pot tandem reaction of 1-arylpenta-3,4-dien-2-ones with activated ketones allowed for an efficient synthesis of 2-arylphenols. Moreover, this reaction was found to be also compatible and combinable with Pd-catalyzed C–H activation and carbonylation of the in situ formed 2-arylphenols to provide dibenzopyranones.


2021 ◽  
Vol 86 (7) ◽  
pp. 5110-5119
Author(s):  
Gao-feng Yang ◽  
Guang-xun Li ◽  
Jin Huang ◽  
Ding-qiang Fu ◽  
Xiao-kang Nie ◽  
...  
Keyword(s):  

ARKIVOC ◽  
2005 ◽  
Vol 2005 (1) ◽  
pp. 92-97 ◽  
Author(s):  
Nicolai Dieltiens ◽  
Christian V. Stevens ◽  
Bart Allaert ◽  
Francis Verpoort

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