scholarly journals Efficient Access to Materials-Oriented Aromatic Alkynes via the Mechanochemical Sonogashira Coupling of Solid Aryl Halides with Large Polycyclic Conjugated Systems

2021 ◽  
Author(s):  
Yunpeng Gao ◽  
Chi Feng ◽  
Tamae Seo ◽  
Koji Kubota ◽  
Hajime Ito
Keyword(s):  
Organic Materials ◽  
Aryl Halides ◽  
Sonogashira Coupling ◽  
Important Research ◽  
Conjugated Systems ◽  
Efficient Access ◽  
Indispensable Tool

Sonogashira coupling represents an indispensable tool for the preparation of organic materials that contain C(sp)–C(sp2) bonds. Improving the efficiency and generality of this methodology has long been an important research...

scholarly journals The Utility of Sonogashira Coupling Reaction for the Derivatization of Aryl Halides with Fluorescent Alkyne

2018 ◽  
Vol 34 (10) ◽  
pp. 1183-1188 ◽  
Author(s):  
Naoyuki YASAKA ◽  
Naoya KISHIKAWA ◽  
Takumi HIGASHIJIMA ◽  
Kaname OHYAMA ◽  
Naotaka KURODA
Keyword(s):  
Coupling Reaction ◽  
Aryl Halides ◽  
Sonogashira Coupling ◽  
Sonogashira Coupling Reaction

Sonogashira Coupling of Aryl Halides Catalyzed by Palladium on Charcoal

2003 ◽  
Vol 68 (8) ◽  
pp. 3327-3329 ◽  
Author(s):  
Zoltán Novák ◽  
András Szabó ◽  
József Répási ◽  
András Kotschy
Keyword(s):  
Aryl Halides ◽  
Sonogashira Coupling

Full Cleavage of C≡C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine

2017 ◽  
Vol 70 (4) ◽  
pp. 421 ◽  
Author(s):  
Sergei F. Vasilevsky ◽  
Maria P. Davydova ◽  
Victor I. Mamatyuk ◽  
Nikolay Tsvetkov ◽  
Audrey Hughes ◽  
...  
Keyword(s):  
Aryl Halides ◽  
The Other ◽  
Keto Group ◽  
Sonogashira Coupling ◽  
Methyl Group ◽  
Concomitant Reduction

Reaction of 1,2-diaminioethane (ethylenediamine) with electron-deficient alkynes leads to full scission of the C≡C bond even in the absence of a keto group directly attached to the alkyne. This process involves oxidation of one of the alkyne carbons into C2 of a 2-R-4,5-dihydroimidazole with the concomitant reduction of the other carbon to a methyl group. The sequence of Sonogashira coupling with the ethylenediamine-mediated fragmentation described in this work can be used for selective formal substitution of halogen in aryl halides by a methyl group or a 4,5-dihydroimidazol-2-yl moiety.

Click Variations on the Synthesis of 2-Nitrophenyl-4-aryl-1,2,3-triazoles without Isolation of 2-Nitrophenyl Azides

Synlett ◽  
2019 ◽  
Vol 31 (06) ◽  
pp. 610-614
Author(s):  
Amélie Roux ◽  
Federico Cisnetti
Keyword(s):  
Sonogashira Coupling ◽  
Aryl Iodides ◽  
Efficient Access ◽  
Metal Catalyzed

We report a series of efficient procedures to prepare 2-nitrophenyl-4-aryl-1,2,3-triazoles avoiding the isolation of potentially hazardous 2-nitrophenyl azides. An organocatalyzed azide-enolate variant allows efficient access to the target compounds while it was shown that a metal-catalyzed azide-alkyne procedure involving a preliminary ­Sonogashira coupling was feasible starting from electron-deficient aryl iodides.

Aqueous Sonogashira coupling of aryl halides with 1-alkynes under mild conditions: use of surfactants in cross-coupling reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (24) ◽  
pp. 18960-18971 ◽  
Author(s):  
Gina M. Roberts ◽  
Wenya Lu ◽  
L. Keith Woo
Keyword(s):  
Aqueous Solutions ◽  
Organic Solvents ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Aryl Bromide ◽  
Sonogashira Coupling ◽  
Mild Conditions ◽  
Cross Coupling Reactions

Aqueous solutions of common and inexpensive surfactants (e.g. SDS and CTAB) are surveyed as an alternative to organic solvents in Sonogashira cross-coupling. Aryl-bromide substrates are best coupled under Cu-free conditions.

One-pot desilylation-Sonogashira coupling

2017 ◽  
Vol 72 (7) ◽  
pp. 489-495
Author(s):  
Jan Horstmann ◽  
Stefanie Reger ◽  
Beate Neumann ◽  
Hans-Georg Stammler ◽  
Norbert W. Mitzel
Keyword(s):  
Aryl Halides ◽  
Sonogashira Coupling ◽  
One Pot

AbstractCoupling of diethynyldiphenylsilane (1) with aryl halides under Sonogashira conditions affords the symmetrical diarylacetylenes bis(2-methylpyridin-5-yl)acetylene (2), bis(4-fluorophenyl)acetylene (3) and bis(4-trifluoromethylphenyl)acetylene (4) in 60% to 82% yield. In the case of 2, the by-product bis(2-methylpyridin-5-yl)butadiyne (2a) was isolated in 12% yield. The occurring desilylation reaction was investigated by treating bis(phenylethynyl)diphenylsilane (5) under the same conditions. The formation of 1-fluoro-4-(phenylethynyl)benzene (6), 1-trifluoromethyl-4-(phenylethynyl)benzene (7) and (tetrafluoropyridin- 4-yl)ethynylbenzene (8) in 70 to 84% yield and the cleavage of hexaphenylcyclotrisiloxane were observed in all cases.

ChemInform Abstract: Phosphine-Free Sonogashira Coupling: Reactions of Aryl Halides Catalyzed by Palladium(II) Complexes of Azetidine-Derived Polyamines under Mild Conditions.

ChemInform ◽  
2009 ◽  
Vol 40 (23) ◽  
Author(s):  
Dong-Hwan Lee ◽  
Young-Hoon Lee ◽  
Jack M. Harrowfield ◽  
Ik-Mo Lee ◽  
Hong In Lee ◽  
...  
Keyword(s):  
Aryl Halides ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Mild Conditions
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