A Convenient and Practical Synthesis of Anisoles and Deuterated Anisoles by Palladium-Catalyzed Coupling Reactions of Aryl Bromides and Chlorides

2012 ◽  
Vol 18 (9) ◽  
pp. 2498-2502 ◽  
Author(s):  
Saravanan Gowrisankar ◽  
Helfried Neumann ◽  
Matthias Beller
Keyword(s):  
Coupling Reactions ◽  
Aryl Bromides ◽  
Palladium Catalyzed ◽  
Practical Synthesis

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: Efficient Palladium-Catalyzed Coupling Reactions of Aryl Bromides and Chlorides with Phenols.

ChemInform ◽  
2010 ◽  
Vol 41 (16) ◽  
Author(s):  
Tongjie Hu ◽  
Thomas Schulz ◽  
Christian Torborg ◽  
Xiaorong Chen ◽  
Jun Wang ◽  
...  
Keyword(s):  
Coupling Reactions ◽  
Aryl Bromides ◽  
Palladium Catalyzed
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