Synthesis of Symmetrical and Unsymmetrical Diarylalkynes from Propiolic Acid Using Palladium-Catalyzed Decarboxylative Coupling

2010 ◽  
Vol 75 (18) ◽  
pp. 6244-6251 ◽  
Author(s):  
Kyungho Park ◽  
Goun Bae ◽  
Jeongju Moon ◽  
Jaehoon Choe ◽  
Kwang Ho Song ◽  
...  
Keyword(s):  
Decarboxylative Coupling ◽  
Palladium Catalyzed ◽  
Propiolic Acid

ChemInform Abstract: Synthesis of Symmetrical and Unsymmetrical Diarylalkynes from Propiolic Acid Using Palladium-Catalyzed Decarboxylative Coupling.

ChemInform ◽  
2010 ◽  
Vol 42 (3) ◽  
pp. no-no
Author(s):  
Kyungho Park ◽  
Goun Bae ◽  
Jeongju Moon ◽  
Jaehoon Choe ◽  
Kwang Ho Song ◽  
...  
Keyword(s):  
Decarboxylative Coupling ◽  
Palladium Catalyzed ◽  
Propiolic Acid

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.

ChemInform Abstract: Palladium-Catalyzed Decarboxylative Coupling of Benzoic Acid Derivatives Using Hydrazone Ligands.

ChemInform ◽  
2014 ◽  
Vol 45 (39) ◽  
pp. no-no
Author(s):  
Takashi Mino ◽  
Eri Yoshizawa ◽  
Kohei Watanabe ◽  
Taichi Abe ◽  
Kiminori Hirai ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
Benzoic Acid Derivatives ◽  
Decarboxylative Coupling ◽  
Palladium Catalyzed ◽  
Hydrazone Ligands

Phosphine-Free Palladium-Catalyzed Decarboxylative Coupling of Alkynylcarboxylic Acids with Aryl and Heteroaryl Halides

2013 ◽  
Vol 355 (4) ◽  
pp. 705-710 ◽  
Author(s):  
Police Vishnuvardhan Reddy ◽  
Pottabathula Srinivas ◽  
Manne Annapurna ◽  
Suresh Bhargava ◽  
Jorg Wagler ◽  
...  
Keyword(s):  
Decarboxylative Coupling ◽  
Palladium Catalyzed

ChemInform Abstract: Regioswitchable Palladium-Catalyzed Decarboxylative Coupling of 1,3-Dicarbonyl Compounds.

ChemInform ◽  
2015 ◽  
Vol 46 (51) ◽  
pp. no-no
Author(s):  
Miles Kenny ◽  
Jeppe Christensen ◽  
Simon J. Coles ◽  
Vilius Franckevicius
Keyword(s):  
Dicarbonyl Compounds ◽  
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

Aryl Chlorides as Coupling Partners in the Palladium-catalyzed Decarboxylative Coupling Reactions of Propiolic Acids

2017 ◽  
Vol 38 (11) ◽  
pp. 1368-1371 ◽  
Author(s):  
Ju-Hyeon Lee ◽  
Gabriel Charles Edwin Raja ◽  
Jimin Kim ◽  
Kye Chun Nam ◽  
Sunwoo Lee
Keyword(s):  
Coupling Reactions ◽  
Aryl Chlorides ◽  
Decarboxylative Coupling ◽  
Palladium Catalyzed

Synthesis of symmetrical diarylalkyne from palladium-catalyzed decarboxylative couplings of propiolic acid and aryl bromides under water

2011 ◽  
Vol 52 (5) ◽  
pp. 576-580 ◽  
Author(s):  
Kyungho Park ◽  
Goun Bae ◽  
Ahbyeol Park ◽  
Yong Kim ◽  
Jaehoon Choe ◽  
...  
Keyword(s):  
Aryl Bromides ◽  
Palladium Catalyzed ◽  
Propiolic Acid
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