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.

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

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.

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.

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.

Application of a 2-aryl indenylphosphine ligand in the Buchwald–Hartwig cross-coupling reactions of aryl and heteroaryl chlorides under the solvent-free and aqueous conditions

2017 ◽  
Vol 15 (27) ◽  
pp. 5805-5810 ◽  
Author(s):  
Yan Liu ◽  
Jia Yuan ◽  
Zi-Fei Wang ◽  
Si-Hao Zeng ◽  
Meng-Yue Gao ◽  
...  
Keyword(s):  
Catalytic System ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Solvent Free ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Aqueous Conditions

An efficient solvent-free and aqueous protocol for the Buchwald–Hartwig cross-coupling reaction has been developed. Notably, the catalytic system also efficiently catalyzed the reaction under aqueous conditions.

Synthesis and Suzuki–Miyaura cross coupling reactions for post-synthetic modification of a tetrabromo-anthracenyl porphyrin

2018 ◽  
Vol 16 (43) ◽  
pp. 8106-8114 ◽  
Author(s):  
Joffrey Pijeat ◽  
Yannick J. Dappe ◽  
Pierre Thuéry ◽  
Stéphane Campidelli
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction

A tetra-bromoanthracenylporphyrin was synthesised and its reactivity was tested by post-synthetic modification using the Suzuki–Miyaura cross coupling reaction.

Functionalized α,β-ynones: efficient ligand for Cu catalyzed Sonogashira-type cross-coupling reaction

RSC Advances ◽  
2016 ◽  
Vol 6 (111) ◽  
pp. 109296-109300 ◽  
Author(s):  
Xian Wang ◽  
Zhenhua Wang ◽  
Zunyuan Xie ◽  
Guofang Zhang ◽  
Weiqiang Zhang ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkynes ◽  
Cross Coupling Reactions ◽  
Aryl Iodides ◽  
Cross Coupling Reaction ◽  
The Cross

1,3-Yones as σ-, π-electron donating ligands significantly accelerated the cross-coupling reactions of aryl iodides with terminal alkynes, in which as low as 0.1 to 1 mol% of CuI were efficiently activated.

scholarly journals Ni-Catalyzed Electrochemical C(sp2)−C(sp3) Cross-Coupling Reactions

2020 ◽  
Author(s):  
Jian Luo ◽  
Bo Hu ◽  
wenda wu ◽  
maowei hu ◽  
Tianbiao Liu
Keyword(s):  
Aryl Halide ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Ambient Conditions ◽  
Acid Modification ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Organozinc Reagents ◽  
Industrial Adoption

Nickel (Ni) catalyzed carbon-carbon (C−C) cross-coupling has been considerably developed in last decades and has demonstrated unique reactivities compared to palladium. However, existing Ni catalyzed cross-coupling reactions, despite success in organic synthesis, are still subject to the use of air-sensitive nucleophiles (i.e. Grignard and organozinc reagents), or catalysts (i.e. Ni<sup>0</sup> pre-catalysts), significantly limiting their academic and industrial adoption. Herein, we report that, through electrochemical voltammetry screening and optimization, the redox neutral C(sp<sup>2</sup>)‒C(sp<sup>3</sup>) cross-coupling can be accomplished in an undivided cell configuration using bench-stable aryl halide or β-bromostyrene (electrophiles) and benzylic trifluoroborate (nucleophiles) reactants, non-precious, bench stable catalysts consisting of NiCl<sub>2</sub>•glyme pre-catalyst and polypyridine ligands under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochemical coupling reaction were confirmed by 48 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Its potential applications were demonstrated by late-stage functionalization of pharmaceuticals and natural amino acid modification. Furthermore, this electrochemical C−C cross-coupling reaction was demonstrated at gram-scale in a flow-cell electrolyzer for practical industrial adoption. Finally, an array of chemical and electrochemical studies mechanistically indicates that electrochemical C−C cross-coupling reaction proceeds through an unconventional radical trans-metalation mechanism.

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