scholarly journals Iron-Catalyzed C–H Functionalizations under Triazole-Assistance

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1806 ◽  
Author(s):  
Matteo Lanzi ◽  
Gianpiero Cera
Keyword(s):  
Transition Metals ◽  
Organic Synthesis ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Efficient Catalyst ◽  
Widespread Application ◽  
Promising Alternative ◽  
Cross Coupling Reactions ◽  
Benign Nature

3d transition metals-catalyzed C–H bond functionalizations represent nowadays an important tool in organic synthesis, appearing as the most promising alternative to cross-coupling reactions. Among 3d transition metals, iron found widespread application due to its availability and benign nature, and it was established as an efficient catalyst in organic synthesis. In this context, the use of ortho-orientating directing groups (DGs) turned out to be necessary for promoting selective iron-catalyzed C–H functionalization reactions. Very recently, triazoles DGs were demonstrated to be more than an excellent alternative to the commonly employed 8-aminoquinoline (AQ) DG, as a result of their modular synthesis as well as the mild reaction conditions applied for their removal. In addition, their tunable geometry and electronics allowed for new unprecedented reactivities in iron-catalyzed C–H activation methodologies that will be summarized within this review.

Comparison of the Suzuki cross-coupling reactions of 4,7-dichloroquinoline and 7-chloro-4-iodoquinoline with arylboronic acids using phosphine-free palladium catalysis in water

2004 ◽  
Vol 82 (2) ◽  
pp. 206-214 ◽  
Author(s):  
Richard W Friesen ◽  
Laird A Trimble
Keyword(s):  
Phenylboronic Acid ◽  
Palladium Catalysis ◽  
Suzuki Reaction ◽  
Tetrabutylammonium Bromide ◽  
Cross Coupling ◽  
Palladium Acetate ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions

4,7-Dichloroquinoline (1a) and 7-chloro-4-iodoquinoline (1b) undergo Suzuki cross-coupling reactions with arylboronic acids catalyzed by phosphine-free palladium acetate in boiling water. Using phenylboronic acid (2), the reaction of 1a provides 7-chloro-4-phenylquinoline (3) (78%) together with diphenylquinoline (4) (12%), while 1b reacts in a much more regioselective fashion and provides 3 in 98% isolated yield. Although 1b undergoes a more regioselective Suzuki reaction than 1a, additional important observations are that the overall reaction of 1b with 2 is three times slower than 1a and that the reaction occurs in the absence of tetrabutylammonium bromide. Using optimized reaction conditions, a variety of aryl and vinylboronic acids undergo regioselective Suzuki cross-coupling with 1b to provide the products 7, 10, and 11 in good to excellent yield.Key words: palladium, cross-coupling, regioselectivity, quinolines, boronic acids.

Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- and Alkynylnaphthoquinones and Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Felipe C. Demidoff ◽  
Leandro L. de Carvalho ◽  
Eduardo José P. Rodrigues Filho ◽  
Andréa Luzia F. de Souza ◽  
Chaquip D. Netto
Keyword(s):  
Click Chemistry ◽  
Organic Synthesis ◽  
Biological Activities ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Large Array ◽  
Terminal Alkyne ◽  
Co Catalyst ◽  
Cross Coupling Reactions ◽  
Convenient Synthesis

AbstractFunctionalized 1,4-naphthoquinones have been employed as versatile synthons in organic synthesis, in addition to presenting a large array of biological activities. Herein, the applications of 2-amino-/ acetylamino-substituted 3-iodo-1,4-naphthoquinones in cross-coupling reactions are described to successfully afford sixteen novel 3-styryl-1,4-naphthoquinones (amino-stilbene-quinone hybrids) and four 3-alkynyl-1,4-naphthoquinone in overall good yields. Interestingly, the alkynylated derivatives could be obtained from ligand- and Pd-free CuI-mediated cross-coupling reactions, after extensive investigations to exclude Pd as a co-catalyst. Lastly, the desilanized terminal alkyne was subjected to click chemistry reactions to give two novel triazole-1,4-naphthoquinone hybrids.

scholarly journals Pd–Ni Bimetallic Nanoparticles Supported on Zro2 as an Efficient Catalyst for Suzuki–Miyaura Reactions

2018 ◽  
Vol 42 (8) ◽  
pp. 419-423
Author(s):  
Li-Jie Zhang ◽  
Xian Yao ◽  
Ying-xin Sun ◽  
Jia-wei Zhang ◽  
Chun Cai
Keyword(s):  
Reduction Method ◽  
Bimetallic Nanoparticles ◽  
Bimetallic Catalyst ◽  
Cross Coupling ◽  
Catalytic Performance ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Excellent Catalytic Performance

Pd–Ni bimetallic nanoparticles (BMNPs) supported on ZrO2 were prepared by an impregnation–reduction method. The BMNPs showed excellent catalytic performance in Suzuki carbon–carbon cross-coupling reactions and almost quantitative conversion of the substrates was obtained under mild conditions in the absence of ligand. The excellent catalytic performance of the bimetallic catalyst could be a result of the synergistic effect between the two metal components. The catalyst showed outstanding recyclability during the reaction process; no obvious decrease in catalytic performance was observed after five cycles.

scholarly journals Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

2018 ◽  
Vol 14 ◽  
pp. 1871-1884 ◽  
Author(s):  
Siva Sankar Murthy Bandaru ◽  
Darinka Dzubiel ◽  
Heiko Ihmels ◽  
Mohebodin Karbasiyoun ◽  
Mohamed M A Mahmoud ◽  
...  
Keyword(s):  
Emission Intensity ◽  
Binding Constants ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Reaction Conditions ◽  
Quadruplex Dna ◽  
Cross Coupling Reactions ◽  
Sonogashira Coupling Reaction

9-Arylbenzo[b]quinolizinium derivatives were prepared with base-free Suzuki–Miyaura coupling reactions between benzo[b]quinolizinium-9-trifluoroborate and selected benzenediazonium salts. In addition, the Sonogashira coupling reaction between 9-iodobenzo[b]quinolizinium and the arylalkyne derivatives yielded four novel 9-(arylethynyl)benzo[b]quinolizinium derivatives under relatively mild reaction conditions. The 9-(N,N-dimethylaminophenylethynyl)benzo[b]quinolizinium is only very weakly emitting, but the emission intensity increases by a factor >200 upon protonation, so that this derivative may operate as pH-sensitive light-up probe. Photometric and fluorimetric titrations of duplex and quadruplex DNA to 9-(arylethynyl)benzo[b]quinolizinium derivatives revealed a significant binding affinity of these compounds towards both DNA forms with binding constants ofKb= 0.2–2.2 × 105M−1.

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.

scholarly journals Palladium-scavenging self-assembled hybrid hydrogels – reusable highly-active green catalysts for Suzuki–Miyaura cross-coupling reactions

2018 ◽  
Vol 9 (46) ◽  
pp. 8673-8681 ◽  
Author(s):  
Petr Slavík ◽  
Dustin W. Kurka ◽  
David K. Smith
Keyword(s):  
Cross Coupling ◽  
Pd Nanoparticles ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Cross Coupling Reactions ◽  
Highly Active ◽  
Hybrid Hydrogels ◽  
Self Assembled

From waste to wealth – a self-assembled hydrogel remediates palladium from solution down to sub-ppm levels, and the resulting gel, which has embedded Pd nanoparticles, acts as a green and efficient catalyst for Suzuki–Miyaura cross-coupling reactions.

A highly efficient catalyst for Suzuki–Miyaura coupling reaction of benzyl chloride under mild conditions

RSC Advances ◽  
2014 ◽  
Vol 4 (69) ◽  
pp. 36437-36443 ◽  
Author(s):  
Zhenhong Guan ◽  
Buyi Li ◽  
Guoliang Hai ◽  
Xinjia Yang ◽  
Tao Li ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Benzyl Chloride ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Microporous Polymers ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Cross Coupling Reactions

Microporous polymers with built-in triphenylphosphine palladium exhibit highly efficient catalytic activity for cross-coupling reactions of benzyl chloride under mild conditions.

A novel and efficient zinc-catalyzed thioetherification of aryl halides

RSC Advances ◽  
2015 ◽  
Vol 5 (41) ◽  
pp. 32675-32678 ◽  
Author(s):  
Amrutha P. Thankachan ◽  
K. S. Sindhu ◽  
K. Keerthi Krishnan ◽  
Gopinathan Anilkumar
Keyword(s):  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Cross Coupling Reactions

The first Zn-catalyzed protocol for C–S cross-coupling reactions for the synthesis of substituted aryl and alkyl sulfides with good yields under mild reaction conditions is described.

Sign in / Sign up

Export Citation Format

Share Document