Palladium-catalyzed selective decarboxylative coupling reaction versus direct C―H arylation for arylation of heteroaromatics

2013 ◽  
Vol 27 (10) ◽  
pp. 595-600 ◽  
Author(s):  
Haiyan Fu ◽  
Hua Chen ◽  
Henri Doucet
Keyword(s):  
Coupling Reaction ◽  
Decarboxylative Coupling ◽  
Palladium Catalyzed

Palladium-catalyzed decarboxylative coupling reaction with alkynyl carboxylic acids and arylsiloxanes

2016 ◽  
Vol 57 (41) ◽  
pp. 4581-4584 ◽  
Author(s):  
Jisun Jang ◽  
Gabriel Charles Edwin Raja ◽  
Ju-Hyeon Lee ◽  
Yujeong Son ◽  
Jimin Kim ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Coupling Reaction ◽  
Decarboxylative Coupling ◽  
Palladium Catalyzed

An unprecedented Pd-catalyzed decarboxylative coupling reaction of aromatic carboxylic acids in aqueous medium under air: synthesis of 3-aryl-imidazo[1,2-a]pyridines from aryl chlorides

2016 ◽  
Vol 14 (1) ◽  
pp. 246-250 ◽  
Author(s):  
Bing Mu ◽  
Yusheng Wu ◽  
Jingya Li ◽  
Dapeng Zou ◽  
Junbiao Chang ◽  
...  
Keyword(s):  
Aqueous Medium ◽  
Carboxylic Acids ◽  
Coupling Reaction ◽  
Aromatic Carboxylic Acids ◽  
Aryl Chlorides ◽  
Decarboxylative Coupling ◽  
Palladium Catalyzed

An efficient and facile protocol for the synthesis of 3-aryl-imidazo[1,2-a]pyridines was investigated via palladium-catalyzed decarboxylative arylation of imidazo[1,2-a]pyridine-3-carboxylic acids.

Palladium-Catalyzed Decarboxylative Coupling Reactions of Propiolic Acid Derivatives and Arylsulfonyl Hydrazide

Synthesis ◽  
2018 ◽  
Vol 50 (16) ◽  
pp. 3197-3204 ◽  
Author(s):  
Kwang Song ◽  
Sunwoo Lee ◽  
Jaerim Park
Keyword(s):  
Functional Groups ◽  
Coupling Reaction ◽  
Coupling Reactions ◽  
Good Tolerance ◽  
Decarboxylative Coupling ◽  
Palladium Catalyzed ◽  
Propiolic Acid

Arylsulfonyl hydrazides were employed as coupling partners for the decarboxylative coupling reaction of propiolic acid derivatives. When the reaction was conducted using Pd(TFA)2 (1.0 mol%), dppp (1.0 mol%), and Cu(OAc)2 (2.4 equiv) in DMF at 100 °C for 0.5 hour, the desired coupled products were formed in moderate to good yields. The reaction showed good tolerance toward functional groups such as ester, ketone, cyano, nitro, chloro, and bromo groups.

scholarly journals Practical synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides via conventional and decarboxylative copper-free Sonogashira coupling reactions

2014 ◽  
Vol 10 ◽  
pp. 384-393 ◽  
Author(s):  
Andrea Caporale ◽  
Stefano Tartaggia ◽  
Andrea Castellin ◽  
Ottorino De Lucchi
Keyword(s):  
Coupling Reaction ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Aryl Bromides ◽  
Wide Range ◽  
Decarboxylative Coupling ◽  
Palladium Catalyzed ◽  
Practical Synthesis ◽  
Propiolic Acid ◽  
Terminal Acetylenes

Two efficient protocols for the palladium-catalyzed synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides in the absence of copper were developed. A simple catalytic system consisting of Pd(OAc)2 and P(p-tol)3 using DBU as the base and THF as the solvent was found to be highly effective for the coupling reaction of 2-methyl-3-butyn-2-ol (4) with a wide range of aryl bromides in good to excellent yields. Analogously, the synthesis of aryl-2-methyl-3-butyn-2-ols was performed also through the decarboxylative coupling reaction of 4-hydroxy-4-methyl-2-pentynoic acid with aryl bromides, using a catalyst containing Pd(OAc)2 in combination with SPhos or XPhos in the presence of tetra-n-butylammonium fluoride (TBAF) as the base and THF as the solvent. Therefore, new efficient approaches to the synthesis of terminal acetylenes from widely available aryl bromides rather than expensive iodides and using 4 or propiolic acid rather than TMS-acetylene as inexpensive alkyne sources are described.

Ferromagnetic Chain Based on Verdazyl-Nitroxide Diradical

2020 ◽  
Author(s):  
Evgeny Tretyakov ◽  
Svetlana Zhivetyeva ◽  
Pavel Petunin ◽  
Dmitry Gorbunov ◽  
Nina Gritsan ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Ferromagnetic Coupling ◽  
Nitronyl Nitroxide ◽  
Triplet Ground State ◽  
One Dimensional ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Ferromagnetic Chain ◽  
High Yields

<p>Verdazyl-nitroxide diradicals were synthesized using the palladium-catalyzed cross-coupling reaction of the corresponding iodoverdazyls with a nitronyl nitroxide-2-ide gold(I) complex with high yields (up to 82%). The synthesized diradicals were found to be highly thermally stable and have a singlet (D<i>E</i><sub>ST</sub> » -64 cm<sup>–1</sup>) or triplet ground state (D<i>E</i><sub>ST</sub> ³ 25 and 100 cm<sup>–1</sup>), depending on which canonical hydrocarbon diradical type they belong to. Upon crystallization, triplet diradicals form unique one-dimensional (1D) spin <i>S</i> = 1 chains of organic diradicals with intrachain ferromagnetic coupling of <i>J</i>′/<i>k</i><sub>B</sub> from 3 to 6 K.</p>

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