Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides via tert-Butyl Isocyanide Insertion

2013 ◽  
Vol 78 (7) ◽  
pp. 3170-3175 ◽  
Author(s):  
Ting Tang ◽  
Xiang-Dong Fei ◽  
Zhi-Yuan Ge ◽  
Zhong Chen ◽  
Yong-Ming Zhu ◽  
...  
Keyword(s):  
Sonogashira Coupling ◽  
Tert Butyl ◽  
Aryl Bromides ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides via tert-Butyl Isocyanide Insertion.

ChemInform ◽  
2013 ◽  
Vol 44 (33) ◽  
pp. no-no
Author(s):  
Ting Tang ◽  
Xiang-Dong Fei ◽  
Zhi-Yuan Ge ◽  
Zhong Chen ◽  
Yong-Ming Zhu ◽  
...  
Keyword(s):  
Sonogashira Coupling ◽  
Tert Butyl ◽  
Aryl Bromides ◽  
Palladium Catalyzed

Correction to Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides Using Near Stoichiometric Carbon Monoxide

2015 ◽  
Vol 17 (10) ◽  
pp. 2566-2566
Author(s):  
Karoline T. Neumann ◽  
Simon R. Laursen ◽  
Anders T. Lindhardt ◽  
Benny Bang-Andersen ◽  
Troels Skrydstrup
Keyword(s):  
Carbon Monoxide ◽  
Sonogashira Coupling ◽  
Aryl Bromides ◽  
Palladium Catalyzed

Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides Using Near Stoichiometric Carbon Monoxide

2014 ◽  
Vol 16 (8) ◽  
pp. 2216-2219 ◽  
Author(s):  
Karoline T. Neumann ◽  
Simon R. Laursen ◽  
Anders T. Lindhardt ◽  
Benny Bang-Andersen ◽  
Troels Skrydstrup
Keyword(s):  
Carbon Monoxide ◽  
Sonogashira Coupling ◽  
Aryl Bromides ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides Using Near Stoichiometric Carbon Monoxide.

ChemInform ◽  
2014 ◽  
Vol 45 (42) ◽  
pp. no-no
Author(s):  
Karoline T. Neumann ◽  
Simon R. Laursen ◽  
Anders T. Lindhardt ◽  
Benny Bang-Andersen ◽  
Troels Skrydstrup
Keyword(s):  
Carbon Monoxide ◽  
Sonogashira Coupling ◽  
Aryl Bromides ◽  
Palladium Catalyzed

Palladium-Catalyzed Carbonylative α-Arylation of tert-Butyl Cyanoacetate with (Hetero)aryl Bromides

2016 ◽  
Vol 81 (4) ◽  
pp. 1358-1366 ◽  
Author(s):  
Mikkel T. Jensen ◽  
Martin Juhl ◽  
Dennis U. Nielsen ◽  
Mikkel F. Jacobsen ◽  
Anders T. Lindhardt ◽  
...  
Keyword(s):  
Tert Butyl ◽  
Aryl Bromides ◽  
Palladium Catalyzed

A General and Convenient Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides

2010 ◽  
Vol 16 (40) ◽  
pp. 12104-12107 ◽  
Author(s):  
Xiao-Feng Wu ◽  
Helfried Neumann ◽  
Matthias Beller
Keyword(s):  
Sonogashira Coupling ◽  
Aryl Bromides ◽  
Palladium Catalyzed

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.

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