scholarly journals Palladium-Catalyzed Terminal Alkyne Coupling Reaction of .BETA.-Bromo-.BETA.-phenylthio or .BETA.-Methylthio-.ALPHA.-trifluoromethyl Enol Ethers: a Convenient Synthesis of 2-Sulfonyl-1-buten-3-ynes.

1999 ◽  
Vol 47 (10) ◽  
pp. 1497-1500 ◽  
Author(s):  
Mitsuhiro YOSHIMATSU ◽  
Sayaka KINOSHITA ◽  
Tomomi SUGIMOTO
Keyword(s):  
Coupling Reaction ◽  
Terminal Alkyne ◽  
Enol Ethers ◽  
Convenient Synthesis ◽  
Palladium Catalyzed ◽  
Alkyne Coupling

Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone

2017 ◽  
Vol 68 (1) ◽  
pp. 180-185
Author(s):  
Adriana Maria Andreica ◽  
Lucia Gansca ◽  
Irina Ciotlaus ◽  
Ioan Oprean
Keyword(s):  
Sex Pheromone ◽  
Coupling Reaction ◽  
Coupling Scheme ◽  
Lithium Aluminium Hydride ◽  
Terminal Alkyne ◽  
Mercury Derivative ◽  
Lithium Aluminium ◽  
Convenient Synthesis ◽  
Practical Synthesis ◽  
Insect Sex

Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
Author(s):  
Jorge A. Cabezas ◽  
Natasha Ferllini
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkyne ◽  
Copper Iodide ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

Convenient synthesis of s-triazine based urea derivatives via a palladium catalyzed C–N coupling reaction

RSC Advances ◽  
2013 ◽  
Vol 3 (23) ◽  
pp. 8960 ◽  
Author(s):  
Jignesh P. Dalvadi ◽  
Poojan K. Patel ◽  
Kishor H. Chikhalia
Keyword(s):  
Coupling Reaction ◽  
Urea Derivatives ◽  
Convenient Synthesis ◽  
Palladium Catalyzed

Fully π-conjugated, diyne-linked covalent organic frameworks formed via alkyne-alkyne cross-coupling reaction

2022 ◽  
Author(s):  
Xiaoming Liu ◽  
Zhengjie Yao ◽  
Zhenwei Zhang ◽  
Jiali Li ◽  
Ji Jia ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Covalent Organic Frameworks ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
New Material ◽  
First Time ◽  
Alkyne Coupling

A novel diyne-linked porphyrin-based COF was constructed through palladium catalyzed alkyne-alkyne coupling for the first time. The new material features inherent porosity, moderate crystallinity, excellent durability, full π-conjugation, and can...

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