Oxidative Coupling and Cross-Coupling of Acetylenic Amines and Acetylenic Carbinols1

1962 ◽  
Vol 27 (5) ◽  
pp. 1587-1591 ◽  
Author(s):  
G. F. Hennion ◽  
Leonard Price
Keyword(s):  
Oxidative Coupling ◽  
Cross Coupling

KI-Promoted Oxidative Coupling of Styrenes with Indoles under Metal-Free Conditions: Facile Access to C-3 Dicarbonyl Indoles

Synthesis ◽  
2019 ◽  
Vol 51 (18) ◽  
pp. 3511-3519
Author(s):  
Bochao Zhou ◽  
Shiyu Guo ◽  
Zheng Fang ◽  
Zhao Yang ◽  
Chengkou Liu ◽  
...  
Keyword(s):  
Efficient Method ◽  
Oxidative Coupling ◽  
Isotope Labeling ◽  
Cross Coupling ◽  
Metal Free ◽  
Broad Scope ◽  
Plausible Mechanism ◽  
Isotope Labeling Experiments

A new and efficient method for the synthesis of C-3 dicarbonyl indoles via oxidative cross-coupling of styrenes with indoles under metal-free conditions has been developed. Moreover, a broad scope of C-3 dicarbonyl indoles in moderate to good yields were obtained, and a plausible mechanism is proposed based on control and isotope-labeling experiments.

Iodine mediated oxidative cross coupling of 2-aminopyridine and aromatic terminal alkyne: a practical route to imidazo[1,2-a]pyridine derivatives

2019 ◽  
Vol 17 (26) ◽  
pp. 6441-6449 ◽  
Author(s):  
Surya Kanta Samanta ◽  
Mrinal K. Bera
Keyword(s):  
Transition Metal ◽  
Oxidative Coupling ◽  
Cross Coupling ◽  
Terminal Alkyne ◽  
Pyridine Derivatives ◽  
Metal Free

A novel, transition-metal free route leading to imidazo[1,2-a]pyridine derivatives via iodine mediated oxidative coupling between 2-aminopyridine and aromatic terminal alkyne has been demonstrated.

scholarly journals Oxidant speciation and anionic ligand effects in the gold-catalyzed oxidative coupling of arenes and alkynes

2019 ◽  
Vol 10 (36) ◽  
pp. 8411-8420 ◽  
Author(s):  
Manuel Hofer ◽  
Teresa de Haro ◽  
Enrique Gómez-Bengoa ◽  
Alexandre Genoux ◽  
Cristina Nevado
Keyword(s):  
Dft Calculations ◽  
Oxidative Coupling ◽  
Cross Coupling ◽  
Reaction Intermediates ◽  
Ligand Effects ◽  
Anionic Ligand

The mechanism of the gold-catalyzed oxidative cross-coupling of arenes and alkynes has been studied in detail combining stoichiometric experiments with putative reaction intermediates and DFT calculations.

Oxidative coupling of Michael acceptors with aryl nucleophiles produced through rhodium-catalyzed C–C bond activation

2017 ◽  
Vol 15 (28) ◽  
pp. 5944-5948 ◽  
Author(s):  
Caroline E. Gregerson ◽  
Kathryn N. Trentadue ◽  
Erik J. T. Phipps ◽  
Janelle K. Kirsch ◽  
Katherine M. Reed ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Bond Activation ◽  
Cross Coupling ◽  
Michael Acceptors

C–C bond activation generates aryl nucleophiles for cross-coupling.

Silicon-Based Reagents for Difluoromethylation and Difluoromethylenation Reactions

Synthesis ◽  
2017 ◽  
Vol 49 (15) ◽  
pp. 3394-3406 ◽  
Author(s):  
Sankarganesh Krishnamoorthy ◽  
G. Prakash
Keyword(s):  
Nucleophilic Substitution ◽  
Oxidative Coupling ◽  
Nucleophilic Addition ◽  
Cross Coupling ◽  
Terminal Alkynes ◽  
Group Transfer ◽  
Recent Developments ◽  
Perfluoroalkyl Group ◽  
Activation Conditions ◽  
Silicon Based

There have been significant developments in the area of perfluoroalkyl group transfer using silicon reagents, specifically in nucleo­philic trifluoromethylation. The mild and versatile activation conditions bestow significant synthetic prowess to the silicon reagents in the area of fluoroalkylations. Owing to the importance of difluoromethylene (CF2) containing compounds in pharmaceuticals, materials, and agrochemicals, several CF2 group transfer methods using related silicon reagents have been developed and studied in detail. This review summarizes the recent developments and trends in this area.1 Introduction2 Trimethyl(trifluoromethyl)silane (Me3SiCF3)3 (Difluoromethyl)trimethylsilane (Me3SiCF2H)3.1 Nucleophilic Addition3.2 Nucleophilic Substitution3.3 Nucleophilic Difluoromethylation of Electron-Deficient Hetero­cycles3.4 Metal-Mediated Cross Coupling3.5 Oxidative Coupling of Terminal Alkynes4 Post-functionalizable Difluoromethyl Transfer Reagents4.1 (Chlorodifluoromethyl)trimethylsilane (Me3SiCF2Cl)4.2 (Bromodifluoromethyl)trimethylsilane (Me3SiCF2Br)4.3 [Difluoro(iodo)methyl]trimethylsilane (Me3SiCF2I)4.4 [Difluoro(phenylthio)methyl]trimethylsilane (Me3SiCF2SPh)4.5 [Difluoro(phenylsulfonyl)methyl]trimethylsilane (Me3SiCF2SO2Ph)4.6 Diethyl [Difluoro(trimethylsilyl)methyl]phosphonate [Me3SiCF2P(O)(OEt)2]4.7 Ethyl Difluoro(trimethylsilyl)acetate (Me3SiCF2CO2Et)4.8 Difluoro(trimethylsilyl)acetamides (Me3SiCF2CONR2)4.9 Difluoro(trimethylsilyl)acetonitrile (Me3SiCF2CN)5 Others6 Conclusions

Access to Biphenyls by Palladium-Catalyzed Oxidative Coupling of Phenyl Carbamates and Phenols

Synthesis ◽  
2019 ◽  
Vol 51 (16) ◽  
pp. 3060-3076 ◽  
Author(s):  
Nadina Truchan ◽  
Christian Jandl ◽  
Alexander Pöthig ◽  
Stefan Breitenlechner ◽  
Thorsten Bach
Keyword(s):  
Trifluoroacetic Acid ◽  
Oxidative Coupling ◽  
Phenyl Ring ◽  
Cross Coupling ◽  
Ortho Position ◽  
Phenyl Substituent ◽  
Steric Factors ◽  
Palladium Catalyzed ◽  
Carbamate Group

The oxidative cross-coupling of phenols (3 equiv) to various substituted phenyl N,N-diethylcarbamates was explored with a variety of substrates. Pd(OAc)2 was employed as the catalyst (20 mol%) and K2S2O8 as the stoichiometric oxidant in trifluoroacetic acid as the solvent (50 °C, 2 h). Carbamates without or with a substituent on the phenyl ring (Me, Ph, Cl, OMe) underwent the reaction unless the phenyl substituent was too strongly electron withdrawing (CN). Cross-coupling occurred exclusively in the ortho position relative to the carbamate group. The regioselectivity at the phenol (ortho or para to hydroxy) was mainly determined by steric factors. Yields up to 60–70% were achieved for specific carbamate/phenol combinations.

scholarly journals Sulfoxide-mediated oxidative cross-coupling of phenols

2020 ◽  
Vol 11 (7) ◽  
pp. 2001-2005 ◽  
Author(s):  
Zhen He ◽  
Gregory J. P. Perry ◽  
David J. Procter
Keyword(s):  
Oxidative Coupling ◽  
Cross Coupling ◽  
Metal Free

A metal-free, oxidative coupling of phenols with various nucleophiles, including arenes, 1,3-diketones and other phenols, is reported.

Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes

2020 ◽  
Author(s):  
Ryan A. Daley ◽  
Joseph Topczewski
Keyword(s):  
Oxidative Coupling ◽  
Field Effect ◽  
Gold Catalyst ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Gold Complexes ◽  
Site Specific ◽  
Effect Parameter ◽  
Oxidative Coupling Reactions

This report details a decarboxylative cross-coupling of (hetero)aryl carboxylates with iodoarenes in the presence of a gold catalyst (>25 examples, up to 96% yield). Generating an aryl nucleophile via decarboxylation obviates problems associated with transmetalation at a putative gold(III) complex. This reaction is site specific, which overcomes prior limitations associated with gold catalyzed oxidative coupling reactions. The reactivity of the (hetero)aryl carboxylate correlates qualitatively to the field effect parameter (Fortho). Furthermore, each step in a proposed mechanism was observed from isolated gold complexes, supporting a gold catalyzed mechanism.

Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes

2020 ◽  
Author(s):  
Ryan A. Daley ◽  
Joseph Topczewski
Keyword(s):  
Oxidative Coupling ◽  
Field Effect ◽  
Gold Catalyst ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Gold Complexes ◽  
Site Specific ◽  
Effect Parameter ◽  
Oxidative Coupling Reactions

This report details a decarboxylative cross-coupling of (hetero)aryl carboxylates with iodoarenes in the presence of a gold catalyst (>25 examples, up to 96% yield). Generating an aryl nucleophile via decarboxylation obviates problems associated with transmetalation at a putative gold(III) complex. This reaction is site specific, which overcomes prior limitations associated with gold catalyzed oxidative coupling reactions. The reactivity of the (hetero)aryl carboxylate correlates qualitatively to the field effect parameter (Fortho). Furthermore, each step in a proposed mechanism was observed from isolated gold complexes, supporting a gold catalyzed mechanism.

scholarly journals Metal-Catalyzed Oxidative Coupling of Ketones and Ketone Enolates

Synthesis ◽  
2018 ◽  
Vol 50 (11) ◽  
pp. 2150-2162 ◽  
Author(s):  
Sandip Murarka ◽  
Andrey Antonchick
Keyword(s):  
Oxidative Coupling ◽  
Cross Coupling ◽  
Building Blocks ◽  
Dicarbonyl Compounds ◽  
Carbocyclic Compounds ◽  
Efficient Access ◽  
Ketone Enolates ◽  
Metal Catalyzed

Recent years have witnessed a significant advancement in the field of radical oxidative coupling of ketones towards the synthesis of highly useful synthetic building blocks, such as 1,4-dicarbonyl compounds, and biologically important heterocyclic and carbocyclic compounds. Besides oxidative homo- and cross-coupling of enolates, other powerful methods involving direct C(sp3)–H functionalizations of ketones­ have emerged towards the synthesis of 1,4-dicarbonyl compounds. Moreover, direct α-C–H functionalization of ketones has also allowed an efficient access to carbocycles and heterocycles. This review summarizes all these developments made since 2008 in the field of metal-catalyzed/promoted radical-mediated functionalization of ketones at the α-position.1 Introduction2 Synthesis of 1,4-Dicarbonyl Compounds3 Synthesis of Heterocyclic Scaffolds4 Synthesis of Carbocyclic Scaffolds5 Conclusion

Sign in / Sign up

Export Citation Format

Share Document