scholarly journals Synthesis of the First Resorcin[4]arene-Functionalized Triazolium Salts and Their Use in Suzuki–Miyaura Cross-Coupling Reactions

Catalysts ◽  
2019 ◽  
Vol 9 (4) ◽  
pp. 388 ◽  
Author(s):  
David Sémeril ◽  
Dominique Matt ◽  
Rengan Ramesh
Keyword(s):  
General Trend ◽  
Cross Coupling ◽  
Reaction Rates ◽  
Metal Center ◽  
Coupling Reactions ◽  
Aryl Chlorides ◽  
Cross Coupling Reactions ◽  
Catalytic Intermediates ◽  
Palladium Catalyzed ◽  
Triazolium Salts

Two bulky triazolium salts, namely 1-{4(24),6(10),12(16),18(22)-tetramethylenedioxy- 2,8,14,20-tetrapentylresorcin[4]arene-5-yl}-4-phenyl-3-methyl-1H-1,2,3-triazolium tetrafluoro borate (1) and 1,4-bis{4(24),6(10),12(16),18(22)-tetramethylenedioxy-2,8,14,20-tetrapentyl resorcin[4]arene-5-yl}-3-methyl-1H-1,2,3-triazolium iodide (2), have been synthesized and assessed in the palladium-catalyzed Suzuki–Miyaura cross-coupling of aryl chlorides, with aryl boronic acids. As a general trend, the reaction rates obtained with 1 were significantly higher (up to 5 times) than those observed for 2, this mainly reflected a sterically more accessible metal center in the catalytic intermediates formed with 1. The presence of flexible pentyl chains in these intermediates, which might sterically interact with the metal center, when the latter adopts an exo-orientation with respect to the cavity, were likely responsible for the observed good performance.

Efficient symmetrical bidentate dioxime ligand-accelerated homogeneous palladium-catalyzed Suzuki–Miyaura coupling reactions of aryl chlorides

2017 ◽  
Vol 41 (1) ◽  
pp. 372-376 ◽  
Author(s):  
Jinyi Song ◽  
Hongyan Zhao ◽  
Yang Liu ◽  
Huatao Han ◽  
Zhuofei Li ◽  
...  
Keyword(s):  
High Activity ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Bidentate Ligands ◽  
Aryl Chlorides ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

A series of N,O-bidentate ligands were synthesized and studied as high activity ligands for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of aryl chlorides with arylboronic acids under mild conditions.

Triazole-Based Monophosphine Ligands for Palladium-Catalyzed Cross-Coupling Reactions of Aryl Chlorides

2006 ◽  
Vol 71 (10) ◽  
pp. 3928-3934 ◽  
Author(s):  
Qian Dai ◽  
Wenzhong Gao ◽  
Duan Liu ◽  
Lea M. Kapes ◽  
Xumu Zhang
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Aryl Chlorides ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

Palladium-Catalyzed Suzuki Cross-Coupling of 2-Halo-Deazapurines with Potassium Organotrifluoroborate Salts in the Regioselective Synthesis of Imidazo[4,5-b]pyridine Analogues

2016 ◽  
Vol 69 (6) ◽  
pp. 618 ◽  
Author(s):  
Bhaskaran Savitha ◽  
Ayyiliath. M. Sajith ◽  
M. Nibin Joy ◽  
K.K. Abdul Khader ◽  
A. Muralidharan ◽  
...  
Keyword(s):  
Comparative Study ◽  
Cross Coupling ◽  
Reaction Rates ◽  
Boronic Acids ◽  
Coupling Reactions ◽  
Coupling Process ◽  
Substantial Role ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
High Yields

In this paper, we report the use of potassium organotrifluoroborate salts as nucleophilic organoboron reagents in the Suzuki cross-coupling reactions of 2-halo deazapurines. Regio-isomeric C-2-substituted imidazo[4,5-b]pyridine analogues were synthesized by employing this protocol in good to excellent yields. Whereas aryl and heteroaryl trifluoroborates reacted readily to give the coupled products in high yields, alkyltrifluoroborates were found to be less reactive. The utilization of tetrabutylammonium acetate was found to play a substantial role in enhancing the reaction rates of the cross-coupling process. Also, a comparative study was performed between boronic acids and potassium organotrifluoroborate salts.

Air-stable phosphine oxides as preligands for catalytic activation reactions of C-Cl, C-F, and C-H bonds

2006 ◽  
Vol 78 (2) ◽  
pp. 209-214 ◽  
Author(s):  
Lutz Ackermann ◽  
Robert Born ◽  
Julia H. Spatz ◽  
Andreas Althammer ◽  
Christian J. Gschrei
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phosphine Oxides ◽  
Aryl Chlorides ◽  
Catalytic Activation ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
Metal Catalyzed

Studies on the use of easily accessible heteroatom-substituted secondary phosphine oxides as preligands for cross-coupling reactions are described. These air-stable sterically hindered phosphine oxides allow for efficient palladium-catalyzed Suzuki- and nickel-catalyzed Kumada-coupling reactions using electronically deactivated aryl chlorides. In addition, they enable nickel-catalyzed coupling reactions of magnesium organyls with aryl fluorides at ambient temperature, and ruthenium-catalyzed coupling reactions of aryl chlorides via C-H bond activation. Finally, the application of modular diamino phosphine chlorides as preligands for a variety of transition-metal-catalyzed C-C and C-N bond formation reactions employing electron-rich aryl chlorides is presented.

[2.2]Paracyclophane-based monophosphine ligand for palladium-catalyzed cross-coupling reactions of aryl chlorides

2009 ◽  
Vol 7 (16) ◽  
pp. 3236 ◽  
Author(s):  
Jiwu Ruan ◽  
Lee Shearer ◽  
Jun Mo ◽  
John Bacsa ◽  
Antonio Zanotti-Gerosa ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Aryl Chlorides ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed
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