Unravelling the Mechanism of Glaser Coupling Reaction on Ag(111) and Cu(111) Surfaces: a Case for Halogen Substituted Terminal Alkyne

2018 ◽  
Vol 122 (26) ◽  
pp. 14537-14545 ◽  
Author(s):  
Tao Wang ◽  
Haifeng Lv ◽  
Lin Feng ◽  
Zhijie Tao ◽  
Jianmin Huang ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Terminal Alkyne ◽  
Glaser 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.

A triptycene-based two-dimensional porous organic polymeric nanosheet

2017 ◽  
Vol 8 (36) ◽  
pp. 5533-5538 ◽  
Author(s):  
Jing-Jing Chen ◽  
Tian-Long Zhai ◽  
Yi-Fan Chen ◽  
Shinan Geng ◽  
Chan Yu ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Liquid Interface ◽  
Two Dimensional ◽  
Air Liquid Interface ◽  
Glaser Coupling

A new application of the “old” Glaser coupling reaction for a two-dimensional porous polymeric nanosheet on an air/liquid interface is developed.

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.

Synthesis of Fréchet-type Dendrimer Using Glaser-type Coupling Reaction of the Terminal Alkyne-focal Dendrons

2014 ◽  
Vol 597 (1) ◽  
pp. 79-87 ◽  
Author(s):  
Seung Choul Han ◽  
Seung Hwan Kwak ◽  
Seong-Hee Yun ◽  
Sung-Ho Jin ◽  
Jae Wook Lee
Keyword(s):  
Coupling Reaction ◽  
Terminal Alkyne ◽  
Type Coupling

Glaser Coupling Reaction without Organic Solvents and Bases under Near-critical Water Conditions

2010 ◽  
Vol 22 (2) ◽  
pp. 219-221 ◽  
Author(s):  
Pin-Hua Li ◽  
Jin-Can Yan ◽  
Min Wang ◽  
Lei Wang
Keyword(s):  
Organic Solvents ◽  
Coupling Reaction ◽  
Water Conditions ◽  
Glaser Coupling

ChemInform Abstract: 3,4-Dihalo-2(5)-furanones: A Novel Oxidant for the Glaser Coupling Reaction.

ChemInform ◽  
2011 ◽  
Vol 42 (34) ◽  
pp. no-no
Author(s):  
Jian-Xiao Li ◽  
Hao-Ran Liang ◽  
Zhao-Yang Wang ◽  
Jian-Hua Fu
Keyword(s):  
Coupling Reaction ◽  
Glaser Coupling

Recent Advances in the Application of Nanometal Catalysts for Glaser Coupling

2020 ◽  
Vol 23 (22) ◽  
pp. 2489-2503 ◽  
Author(s):  
Saeideh Ebrahimiasl ◽  
Farnaz Behmagham ◽  
Shahrzad Abdolmohammadi ◽  
Rahman N. Kojabad ◽  
Esmail Vessally
Keyword(s):  
Transition Metal ◽  
Molecular Oxygen ◽  
Coupling Reaction ◽  
Terminal Alkynes ◽  
Oxidative Process ◽  
Copper Salts ◽  
Catalytic Systems ◽  
Transition Metal Nanoparticles ◽  
The Past ◽  
Glaser Coupling

: Synthesis of symmetrical 1,3-diynes from terminal alkynes through an oxidative process is generally called Glaser coupling. The classic Glaser coupling is catalyzed by copper salts under an atmosphere of molecular oxygen as an oxidant. Over the past years, different metal catalysts and oxidants were successfully used in this atom economical C-C coupling reaction. Moreover, several procedures for the preparation of unsymmetrical 1,3-diynes by coupling two different alkyne substrates have been developed. In this review, we will highlight the usefulness of transition metal nanoparticles as efficient catalysts in homo- and hetero-coupling of alkynes by hoping that it will be beneficial to the development of novel and extremely efficient catalytic systems for this fast-growing and important reaction.

An efficient alkynylation of 4-thiazolidinone with terminal alkyne under C–H functionalisation

RSC Advances ◽  
2016 ◽  
Vol 6 (56) ◽  
pp. 50780-50785 ◽  
Author(s):  
Mohammed Umar M. Shaikh ◽  
Sulochana S. Mudaliar ◽  
Kishor H. Chikhalia
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Terminal Alkynes ◽  
Terminal Alkyne ◽  
Cross Coupling Reaction ◽  
The Cross

A method of palladium catalysed efficient alkynylation through the cross coupling reaction of terminal alkynes with the slightly more acidic C–H bonds of 4-thiazolidinone has been developed.

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