Visible Light Mediated Synthesis of Rutaecarpine Alkaloids Through C-N Cross-coupling Reaction

Synlett ◽  
2021 ◽  
Author(s):  
Dong Chen ◽  
Shiqing Li ◽  
Jinhua Wang ◽  
Tiantian Gou ◽  
Linfeng Zhang ◽  
...  

A visible-light-initiated cross-dehydrogenative-coupling amination is described, featuring metal- and photocatalyst-free, at room temperature, and using air as an oxidant. The reaction provides a facile approach for the synthesis of rutaecarpine and its derivatives. The substrates with electron-withdrawing groups give higher yields than those with electron-donating groups, but the substituent position has a negligible influence on the yield. Using binaphthyl-diyl hydrogen phosphate and dibenzyl phosphate as catalysts both deliver satisfying yields.This straight-forward light-driven strategy might be applicable to the synthesis of quinazolinone derivatives.

2016 ◽  
Vol 18 (16) ◽  
pp. 4526-4530 ◽  
Author(s):  
Arunachalam Sagadevan ◽  
Ping-Chiang Lyu ◽  
Kuo Chu Hwang

An efficient and eco-friendly approach to Csp–Csp cross-coupling of terminal alkynes for the construction of unsymmetrical conjugated diynes via a visible-light-induced CuCl catalysed process at room temperature is described.


Synlett ◽  
2017 ◽  
Vol 28 (16) ◽  
pp. 2153-2156 ◽  
Author(s):  
Wen-Ting Wei ◽  
Hongze Liang ◽  
Wen-Ming Zhu ◽  
Weida Liang ◽  
Yi Wu ◽  
...  

A radical–radical cross-coupling reaction of phenols with tert-butyl nitrite has been developed with the use of water as an additive. This method allows the construction of C–N bonds under an air atmosphere at room temperature, providing the ortho-nitrated phenol derivative in moderate to good yields.


Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2714 ◽  
Author(s):  
Matteo Savastano ◽  
Paloma Arranz-Mascarós ◽  
Maria Paz Clares ◽  
Rafael Cuesta ◽  
Maria Luz Godino-Salido ◽  
...  

A new G-(H2L)-Pd heterogeneous catalyst has been prepared via a self-assembly process consisting in the spontaneous adsorption, in water at room temperature, of a macrocyclic H2L ligand on graphene (G) (G + H2L = G-(H2L)), followed by decoration of the macrocycle with Pd2+ ions (G-(H2L) + Pd2+ = G-(H2L)-Pd) under the same mild conditions. This supramolecular approach is a sustainable (green) procedure that preserves the special characteristics of graphene and furnishes an efficient catalyst for the Cu-free Sonogashira cross coupling reaction between iodobenzene and phenylacetylene. Indeed, G-(H2L)-Pd shows an excellent conversion (90%) of reactants into diphenylacetylene under mild conditions (50 °C, water, aerobic atmosphere, 14 h). The catalyst proved to be reusable for at least four cycles, although decreasing yields down to 50% were observed.


RSC Advances ◽  
2016 ◽  
Vol 6 (34) ◽  
pp. 28981-28985 ◽  
Author(s):  
Manashi Sarmah ◽  
Anindita Dewan ◽  
Manoj Mondal ◽  
Ashim J. Thakur ◽  
Utpal Bora

The conversion of waste papaya-bark to ash–water extract via low-temperature combustion, and its utilization as an efficient and eco-friendly in situ basic medium for Suzuki–Miyaura cross-coupling reaction at room temperature are reported.


RSC Advances ◽  
2015 ◽  
Vol 5 (48) ◽  
pp. 38085-38092 ◽  
Author(s):  
Tahshina Begum ◽  
Manoj Mondal ◽  
Pradip K. Gogoi ◽  
Utpal Bora

A novel Pd@imine-SiO2 catalyst was prepared and found to exhibit excellent catalytic activity in a Suzuki-Miyaura cross-coupling reaction under aqueous media at room temperature.


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