Improved Synthesis of Symmetrical 2,5-Diarylimidazoles by One-Pot Palladium-Catalyzed Direct Arylation Tailored on the Electronic Features of the Aryl Halide

Synthesis ◽  
2017 ◽  
Vol 49 (20) ◽  
pp. 4676-4686 ◽  
Author(s):  
Marco Lessi ◽  
Gianmarco Panzetta ◽  
Giulia Marianetti ◽  
Fabio Bellina
Keyword(s):  
Aryl Halide ◽  
One Pot ◽  
Direct Arylation ◽  
One Pot Synthesis ◽  
Aryl Bromides ◽  
Palladium Catalyzed ◽  
The One

Two methods for the one-pot synthesis of 2,5-diarylimidazoles by palladium-catalyzed direct C–H arylation of 1-substituted imidazoles with aryl bromides have been devised. The first method, promoted by copper(I) iodide, is best suited for electron-poor aryl bromides, and also allows the 2,5-diarylation of thiazole and oxazole. The use of xylene instead of DMA is the key for the efficiency of the second method, which gives the best results with electron-rich aryl bromides.

Palladium-Catalyzed Copper-Free Sonogashira Coupling of 2-Bromoarylcarbonyls: Synthesis of Isobenzofurans via One-Pot Reductive Cyclization

Synthesis ◽  
2017 ◽  
Vol 49 (23) ◽  
pp. 5149-5158
Author(s):  
Alavala Krishna Reddy ◽  
Gedu Satyanarayana
Keyword(s):  
Reductive Cyclization ◽  
Sonogashira Coupling ◽  
One Pot ◽  
One Pot Synthesis ◽  
Palladium Catalyzed ◽  
The One

Palladium-catalyzed copper-free Sonogashira coupling of 2-bromocarbonyls is presented. This method afforded the 2-alkynylaryl carbonyls, useful synthons for the accomplishment of many carbocyclic and heterocyclic motifs. Significantly, the strategy was extended to the one-pot synthesis of isobenzofurans via reduction followed by intramolecular 5-exo-dig cyclization.

scholarly journals One-Pot Synthesis of B-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed Reactions

Catalysts ◽  
2020 ◽  
Vol 10 (11) ◽  
pp. 1348
Author(s):  
Sergey A. Anufriev ◽  
Akim V. Shmal’ko ◽  
Kyrill Yu. Suponitsky ◽  
Igor B. Sivaev
Keyword(s):  
Functional Groups ◽  
X Ray Diffraction ◽  
One Pot ◽  
One Pot Synthesis ◽  
Palladium Catalyzed ◽  
Catalyzed Reactions ◽  
The One ◽  
Solid State Structures ◽  
Derivatives Of

The simple and efficient method was developed for the one-pot synthesis of B-substituted aryl derivatives of ortho-carborane with functional groups sensitive to organolithium and organomagnesium reagents using 9-iodo-ortho-carborane and generated in situ organozinc compounds. The method proposed was used to prepare a series of 9-aryl-ortho-carboranes, including those containing nitrile and ester groups, 9-RC6H4-1,2-C2B10H11 (R = p-Me, p-NMe2, p-OCH2OMe, o-OMe, p-OMe, o-CN, p-CN, o-COOEt, m-COOEt, and p-COOEt). It was demonstrated that the same approach can be used for synthesis of diaryl derivatives of ortho-carborane 9,12-(RC6H4)2-1,2-C2B10H10 (R = H, p-Me). The solid-state structures of 9-RC6H4-1,2-C2B10H11 (R = p-NMe2, p-OCH2OMe, o-OMe, o-CN, p-CN, m-COOEt, and p-COOEt) and 9,12-(p-MeC6H4)2-1,2-C2B10H10 were determined by single crystal X-ray diffraction.

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