Selectfluor-induced C(sp2)–O coupling reaction of N-substituted anilines with hydroxylamine derivatives

2018 ◽  
Vol 16 (33) ◽  
pp. 6017-6024 ◽  
Author(s):  
Bin Sun ◽  
Shi Yin ◽  
Xiaohui Zhuang ◽  
Can Jin ◽  
Weike Su
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Substituted Anilines ◽  
Metal Free ◽  
Cross Coupling Reactions ◽  
Hydroxylamine Derivatives

We developed a novel metal-free method for the construction of C(sp2)–O bonds via oxidative cross-coupling reactions between various N-substituted anilines and hydroxylamine derivatives just using commercially available Selectfluor as an oxidant.

Metal-free Oxidative Cross-Coupling Reaction of Aromatic Compounds Containing Heteroatoms

Synlett ◽  
2017 ◽  
Vol 28 (14) ◽  
pp. 1680-1694 ◽  
Author(s):  
Koji Morimoto ◽  
Toshifumi Dohi ◽  
Yasuyuki Kita
Keyword(s):  
Aromatic Compounds ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Hypervalent Iodine ◽  
Coupling Reactions ◽  
Heteroaromatic Compounds ◽  
Metal Free ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Biaryl Coupling

The biaryl unit containing a heteroatom is a key structure in a large number of natural products and π-conjugated organic systems. The cross-couplings can provide powerful methods for the construction of biaryls and heterobiaryls; thus the development of a new coupling method has been intensively studied by synthetic chemists. Therefore, the oxidative biaryl coupling reaction of arenes containing a heteroatom is a significantly attractive, convenient, and straightforward route to the synthesis of biaryls due to its operational simplicity avoiding the preparation of the corresponding halogenated and metallated arenes. In this report, recent progress in the field of metal-free oxidative cross-coupling reactions of aromatic compounds using hypervalent iodine(III) reagents, is presented.1 Introduction2 Cyanation and Halogenation Reactions of Heteroaromatic Compounds3 Biaryl Coupling Reaction of Heteroaromatic Compounds3.1 Regioselective Coupling Reaction of Thiophenes3.2 Cross-Coupling Reaction of Thiophenes3.3 Coupling Reaction of EDOT and Pyrroles3.4 Cross-Coupling Reaction of Pyrroles4 Cross-Coupling Reaction of Anilines5 Cross-Coupling Reaction of Phenols6 Cross-Coupling Reaction of N-Heteroaromatics with Aryl Radicals from Diaryliodonium(III) Salts7 Conclusion

Metal-free intermolecular C–O cross-coupling reactions: synthesis of N-hydroxyimide esters

RSC Advances ◽  
2016 ◽  
Vol 6 (96) ◽  
pp. 93486-93490 ◽  
Author(s):  
Yunhe Lv ◽  
Kai Sun ◽  
Weiya Pu ◽  
Shukuan Mao ◽  
Gang Li ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Metal Free ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction

Selectfluor-mediated intermolecular C–O cross coupling reaction for the synthesis of N-hydroxyimide esters was achieved under metal-free conditions.

An Iron-Based Catalyst Enables The Enantioconvergent Synthesis of Chiral 1,1-Diarylalkanes Through a Suzuki-Miyaura Cross-Coupling Reaction

2020 ◽  
Author(s):  
Chet Tyrol ◽  
Nang Yone ◽  
Connor Gallin ◽  
Jeffery Byers
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Radical Intermediates ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Centered Radical ◽  
Iron Based ◽  
High Yields

By using an iron-based catalyst, access to enantioenriched 1,1-diarylakanes was enabled through an enantioselective Suzuki-Miyaura crosscoupling reaction. The combination of a chiral cyanobis(oxazoline) ligand framework and 1,3,5-trimethoxybenzene additive were essential to afford high yields and enantioselectivities in cross-coupling reactions between unactivated aryl boronic esters and a variety of benzylic chlorides, including challenging ortho-substituted benzylic chloride substrates. Mechanistic investigations implicate a stereoconvergent pathway involving carbon-centered radical intermediates.

Synthesis of Alkyl-Substituted Pyrazine N -Oxides by Transition-Metal-Free Oxidative Cross-Coupling Reactions

2018 ◽  
Vol 7 (6) ◽  
pp. 1118-1123 ◽  
Author(s):  
Miao Lai ◽  
Yuan Li ◽  
Zhiyong Wu ◽  
Mingqin Zhao ◽  
Xiaoming Ji ◽  
...  
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Metal Free ◽  
Cross Coupling Reactions

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.

The Synthesis of Pharmaceuticals: The Effective Application of Secondary Boronic Esters in Enantioselective Suzuki ‐ Miyaura Cross ‐ Coupling Reactions

2016 ◽  
Author(s):  
Jonathon Moir
Keyword(s):  
Natural Products ◽  
Human Life ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Carbon Bonds ◽  
Effective Drugs

Pharmaceuticals and drugs have become an indispensable part of human life. Presently, a myriad of different drugs are available for a variety of mental and physical health concersn. The synthesis of these drugs, however, remains an elusive and often difficult aspect of the industry. The importance of chirality, or "handedness", in the synthesis of natural products is paramount, as any given pair of enantiomers can have widely differing physiological effects. As such, the ability to control the enantioselectivity of a reaction is of the utmost importance. One example of a facile method used to form carbon-carbon bonds is the Suzuki-Miyaura cross-coupling reaction. Not only is this reaction effective at coupling primary organoboronic esters with organohalides, but recent work in the Crudden group in the Department of Chemistry has revealed an effective method of also cross-couplingchiral secondary organoboronic esters with good retention of stereochemistry. This work, the first of its kind, is crucial in developing single-handed natural products for a wide array of applications, including applications in the pharmaceutical industry. The end result is safer and more effective drugs for distribution to the general public. To expand the scope of this project, new substrates are currently being synthesized for cross-coupling applications. The overall goal is to improve upon current methodologies, while helping to meet the industrial and academic needs of the future.  

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 Synthesis of 4-Alkyl-4H-1,2,4-triazole Derivatives by Suzuki Cross-coupling Reactions and Their Luminescence Properties

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 652 ◽  
Author(s):  
Monika Olesiejuk ◽  
Agnieszka Kudelko ◽  
Marcin Swiatkowski ◽  
Rafal Kruszynski
Keyword(s):  
Ionic Liquids ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Luminescence Properties ◽  
Coupling Reactions ◽  
Triazole Derivatives ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Derivatives Of

New derivatives of 4-alkyl-3,5-diaryl-4H-1,2,4-triazole were synthesized utilizing the Suzuki cross-coupling reaction. The presented methodology comprises of the preparation of bromine-containing 4-alkyl-4H-1,2,4-triazoles and their coupling with different commercially available boronic acids in the presence of ionic liquids or in conventional solvents. The obtained compounds were tested for their luminescence properties.

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.

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