scholarly journals Denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids

2017 ◽  
Vol 8 (5) ◽  
pp. 3852-3857 ◽  
Author(s):  
Yuanhao Wang ◽  
Yunfei Wu ◽  
Yuanhe Li ◽  
Yefeng Tang

Palladium-catalyzed denitrogenative Suzuki and carbonylative Suzuki reactions of benzotriazoles with boronic acids have been achieved through the in situ generation of ortho-amino-arenediazonium species.

RSC Advances ◽  
2018 ◽  
Vol 8 (70) ◽  
pp. 40000-40015 ◽  
Author(s):  
Nedra Touj ◽  
Abdullah S. Al-Ayed ◽  
Mathieu Sauthier ◽  
Lamjed Mansour ◽  
Abdel Halim Harrath ◽  
...  

The in situ prepared four component system Pd(OAc)2, 1,3-dialkylbenzimidazolium halides 2a–i and 4a–i, K2CO3 under CO atmosphere catalyses carbonylative cross-coupling reaction of 2-bromopyridine with various boronic acids to yield unsymmetrical arylpyridine ketones.


RSC Advances ◽  
2019 ◽  
Vol 9 (2) ◽  
pp. 675-675 ◽  
Author(s):  
Nedra Touj ◽  
Abdullah S. Al-Ayed ◽  
Mathieu Sauthier ◽  
Lamjed Mansour ◽  
Abdel Halim Harrath ◽  
...  

Correction for ‘Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)2 catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities’ by Nedra Touj et al., RSC Adv., 2018, 8, 40000–40015.


2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Shaoyu Mai ◽  
Wendong Li ◽  
Xue Li ◽  
Yingwei Zhao ◽  
Qiuling Song

AbstractCross-coupling reactions involving metal carbene intermediates play an increasingly important role in C–C bond formation. Expanding the carbene precursors to a broader range of starting materials and more diverse products is an ongoing challenge in synthetic organic chemistry. Herein, we report a Suzuki-Miyaura coupling reaction of in situ-generated Pd–carbene complexes via desulfurization of thioureas or thioamides. This strategy enables the preparation of a broad array of substituted amidinium salts and unsymmetrical diaryl ketones. The reaction is readily scalable, compatible with bromo groups on aromatic rings, tolerant to moisture and air and has a broad substrate scope. Furthermore, a single crystal structure of Pd-diaminocarbene complex is obtained and proven to be the key intermediate in both catalytic and stoichiometric reactions. Preliminary mechanistic studies demonstrate the dual role of the silver salt as a desulfurating reagent assisting the elimination of sulfur and as oxidant facilitating the PdII/Pd0/PdII catalytic cycle.


2011 ◽  
Vol 353 (10) ◽  
pp. 1671-1675 ◽  
Author(s):  
Wenjie Li ◽  
Joe J. Gao ◽  
Yongda Zhang ◽  
Wenjun Tang ◽  
Heewon Lee ◽  
...  

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