Novel and Unexpected Deamination during the Palladium-Catalysed Cross-Coupling of Haloanilines and Arylboronic Acids

Synlett ◽  
1999 ◽  
Vol 1999 (4) ◽  
pp. 438-440 ◽  
Author(s):  
Michael Hird ◽  
Alexander J. Seed ◽  
Kenneth J. Toyne
Keyword(s):  
Cross Coupling ◽  
Arylboronic Acids

scholarly journals Cu(OTf)2‐Mediated Cross‐Coupling of Nitriles and N‐Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products

2021 ◽  
Author(s):  
Allan J. B. Watson ◽  
Nicola L. Bell ◽  
Chao Xu ◽  
James W. B. Fyfe ◽  
Julien C. Vantourout ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Arylboronic Acids

Comparison of the Suzuki cross-coupling reactions of 4,7-dichloroquinoline and 7-chloro-4-iodoquinoline with arylboronic acids using phosphine-free palladium catalysis in water

2004 ◽  
Vol 82 (2) ◽  
pp. 206-214 ◽  
Author(s):  
Richard W Friesen ◽  
Laird A Trimble
Keyword(s):  
Phenylboronic Acid ◽  
Palladium Catalysis ◽  
Suzuki Reaction ◽  
Tetrabutylammonium Bromide ◽  
Cross Coupling ◽  
Palladium Acetate ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions

4,7-Dichloroquinoline (1a) and 7-chloro-4-iodoquinoline (1b) undergo Suzuki cross-coupling reactions with arylboronic acids catalyzed by phosphine-free palladium acetate in boiling water. Using phenylboronic acid (2), the reaction of 1a provides 7-chloro-4-phenylquinoline (3) (78%) together with diphenylquinoline (4) (12%), while 1b reacts in a much more regioselective fashion and provides 3 in 98% isolated yield. Although 1b undergoes a more regioselective Suzuki reaction than 1a, additional important observations are that the overall reaction of 1b with 2 is three times slower than 1a and that the reaction occurs in the absence of tetrabutylammonium bromide. Using optimized reaction conditions, a variety of aryl and vinylboronic acids undergo regioselective Suzuki cross-coupling with 1b to provide the products 7, 10, and 11 in good to excellent yield.Key words: palladium, cross-coupling, regioselectivity, quinolines, boronic acids.

scholarly journals 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

RSC Advances ◽  
2018 ◽  
Vol 8 (70) ◽  
pp. 40000-40015 ◽  
Author(s):  
Nedra Touj ◽  
Abdullah S. Al-Ayed ◽  
Mathieu Sauthier ◽  
Lamjed Mansour ◽  
Abdel Halim Harrath ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Suzuki Coupling ◽  
Boronic Acids ◽  
Cytotoxic Activities ◽  
Coupling Reactions ◽  
Component System ◽  
Arylboronic Acids ◽  
Cross Coupling Reaction

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.

Cross-coupling reaction between arylboronic acids and carboranyl iodides catalyzed by graphene oxide (GO)-supported Pd(0) recyclable nanoparticles for the synthesis of carboranylaryl ketones

2014 ◽  
Vol 43 (13) ◽  
pp. 5014-5020 ◽  
Author(s):  
Algin Oh Biying ◽  
Venu R. Vangala ◽  
Chia Sze Chen ◽  
Ludger Paul Stubs ◽  
Narayan S. Hosmane ◽  
...  
Keyword(s):  
Graphene Oxide ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Arylboronic Acids ◽  
Cross Coupling Reaction ◽  
Supported Pd
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