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.

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.

Efficient synthesis of 2-phenyl-3-substituted furo/thieno[2,3-b]quinoxalines via Sonogashira coupling reaction followed by iodocyclization and subsequent palladium-catalyzed cross-coupling reactions

RSC Advances ◽  
2016 ◽  
Vol 6 (87) ◽  
pp. 83901-83908 ◽  
Author(s):  
Tayebeh Besharati-Seidani ◽  
Ali Keivanloo ◽  
Babak Kaboudin ◽  
Tsutomu Yokomatsu
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Efficient Synthesis ◽  
Cross Coupling Reactions ◽  
Sonogashira Coupling Reaction ◽  
Quinoxaline Derivatives ◽  
Palladium Catalyzed

In this paper, we report the successful synthesis of new 2-phenyl-3-substituted furo/thieno[2,3-b]quinoxaline derivatives from 2-chloro-3-methoxyquinoxaline and 2-chloro-3-(methylthio)quinoxaline by a three-step approach.

The reaction of porphyrins with α,β-acetylenic ketone/ester (Morita-Baylis-Hillman) promoted by MgI2 and subsequent Sonogashira coupling reactions

2006 ◽  
Vol 10 (10) ◽  
pp. 1172-1178 ◽  
Author(s):  
Naseem Ahmed ◽  
Hasrat Ali ◽  
Johan E. van Lier
Keyword(s):  
Lewis Acid ◽  
Stereoselective Synthesis ◽  
Coupling Reaction ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Three Component Reaction ◽  
Palladium Catalyzed ◽  
Michael Type Addition ◽  
Acetylenic Ketone ◽  
Ketone Ester

The stereoselective synthesis of (Z)-β-iodovinyl ketones/esters of Morita-Baylis-Hillman (MBH) porphyrin adducts has been achieved with a tandem formation of C - C and C - I bonds in a three-component reaction. The reaction is promoted by MgI 2 as a Lewis acid, as well as an iodine source for a Michael-type addition. The MBH adducts are efficiently oxidized to the corresponding ketones with Dess-Martin periodinane (DMP). These scaffolds are further used in a palladium-catalyzed Sonogashira carbon-carbon coupling reaction to obtain highly extended porphyrin systems.

Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Crosscoupling Reactions

2020 ◽  
Vol 24 (3) ◽  
pp. 231-264 ◽  
Author(s):  
Kevin H. Shaughnessy
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Wide Range ◽  
Sterically Demanding ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Phosphines are widely used ligands in transition metal-catalyzed reactions. Arylphosphines, such as triphenylphosphine, were among the first phosphines to show broad utility in catalysis. Beginning in the late 1990s, sterically demanding and electronrich trialkylphosphines began to receive attention as supporting ligands. These ligands were found to be particularly effective at promoting oxidative addition in cross-coupling of aryl halides. With electron-rich, sterically demanding ligands, such as tri-tertbutylphosphine, coupling of aryl bromides could be achieved at room temperature. More importantly, the less reactive, but more broadly available, aryl chlorides became accessible substrates. Tri-tert-butylphosphine has become a privileged ligand that has found application in a wide range of late transition-metal catalyzed coupling reactions. This success has led to the use of numerous monodentate trialkylphosphines in cross-coupling reactions. This review will discuss the general properties and features of monodentate trialkylphosphines and their application in cross-coupling reactions of C–X and C–H bonds.

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
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