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.

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.

Metal-free oxidative coupling of quinoxalin-2(1H)-ones with arylaldehydes leading to 3-acylated quinoxalin-2(1H)-ones

2018 ◽  
Vol 16 (17) ◽  
pp. 3203-3212 ◽  
Author(s):  
Jin-Wei Yuan ◽  
Jun-Hao Fu ◽  
Shuai-Nan Liu ◽  
Yong-Mei Xiao ◽  
Pu Mao ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Free ◽  
Aryl Aldehydes ◽  
Mild Conditions ◽  
Cross Coupling Reaction

An efficient protocol for the synthesis of 3-aroylquinoxalin-2(1H)-ones has been developed via a metal-free oxidative cross-coupling reaction of quinoxalin-2(1H)-ones with aryl aldehydes under mild conditions with good yields.

Direct C-4 alkylation of quinazoline N-oxides with ethers via an oxidative cross-coupling reaction under metal-free conditions

2018 ◽  
Vol 16 (45) ◽  
pp. 8724-8731 ◽  
Author(s):  
Qin Yang ◽  
Minhao Lou ◽  
Zhijian Yin ◽  
Zhihong Deng ◽  
Qiuping Ding ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Free ◽  
Cross Coupling Reaction

A novel and efficient protocol for the direct C-4 alkylation of quinazoline-3-oxides via radical oxidative coupling between quinazoline 3-oxides and ethers in the presence of TBHP is presented.

Metal-Free Photoredox-Catalyzed C–H/C–H Coupling of Arenes Enabled by Interrupted Pummerer Activation

2019 ◽  
Author(s):  
Miles Aukland ◽  
Mindaugas Šiaučiulis ◽  
Adam West ◽  
Gregory Perry ◽  
David Procter
Keyword(s):  
Natural Product ◽  
Selective Reduction ◽  
Cross Coupling ◽  
One Pot ◽  
Complex Molecules ◽  
Pummerer Reaction ◽  
Metal Free ◽  
Bond Forming ◽  
Coupling Partner ◽  
Bioactive Natural Product

<p>Aryl–aryl cross-coupling constitutes one of the most widely used procedures for the synthesis of high-value materials, ranging from pharmaceuticals to organic electronics and conducting polymers. The assembly of (hetero)biaryl scaffolds generally requires multiple steps; coupling partners must be functionalized before the key bond-forming event is considered. Thus, the development of selective C–H arylation processes in arenes, that side-step the need for prefunctionalized partners, is crucial for streamlining the construction of these key architectures. Here we report an expedient, one-pot assembly of (hetero)biaryl motifs using photocatalysis and two non-prefunctionalized arene partners. The approach is underpinned by the activation of a C–H bond in an arene coupling partner using the interrupted Pummerer reaction. A unique pairing of the organic photoredox catalyst and the intermediate dibenzothiophenium salts enables highly selective reduction in the presence of sensitive functionalities. The utility of the metal-free, one-pot strategy is exemplified by the synthesis of a bioactive natural product and the modification of complex molecules of societal importance.</p>

scholarly journals Transition-Metal-Free Cross-Coupling of Aryl Halides with Arylstannanes

2021 ◽  
Author(s):  
Qing He ◽  
Wenli Wang ◽  
Yong Liang ◽  
Zunting Zhang ◽  
Stanislaw F. Wnuk
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Metal Free

scholarly journals Metal-free oxidative cross-coupling enabled practical synthesis of atropisomeric QUINOL and its derivatives

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Peng-Ying Jiang ◽  
Kai-Fang Fan ◽  
Shaoyu Li ◽  
Shao-Hua Xiang ◽  
Bin Tan
Keyword(s):  
Asymmetric Catalysis ◽  
Kinetic Resolution ◽  
Academic Research ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Industrial Applications ◽  
Lewis Base ◽  
Production Costs ◽  
Metal Free ◽  
Base Catalysts

AbstractAs an important platform molecule, atropisomeric QUINOL plays a crucial role in the development of chiral ligands and catalysts in asymmetric catalysis. However, efficient approaches towards QUINOL remain scarce, and the resulting high production costs greatly impede the related academic research as well as downstream industrial applications. Here we report a direct oxidative cross-coupling reaction between isoquinolines and 2-naphthols, providing a straightforward and scalable route to acquire the privileged QUINOL scaffolds in a metal-free manner. Moreover, a NHC-catalyzed kinetic resolution of QUINOL N-oxides with high selectivity factor is established to access two types of promising axially chiral Lewis base catalysts in optically pure forms. The utility of this methodology is further illustrated by facile transformations of the products into QUINAP, an iconic ligand in asymmetric catalysis.

A Three Component Iodine-Catalyzed Oxidative Coupling Reaction: A Heterodifunction of 3-Methylindole

2021 ◽  
Author(s):  
Wei Zhang ◽  
Shiqun Xiang ◽  
Weibin Fan ◽  
Jiang Jin ◽  
Yinghua Li ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Peroxy Radicals ◽  
Metal Free ◽  
Tert Butyl ◽  
Oxidative Coupling Reaction

A metal-free synthesis of heterodifunctional indole derivaties is developed through TBHP/KI-mediated oxidative coupling. The reaction constructs C-O and C-C bonds in succession with the help of tert-butyl peroxy radicals generated...

Synthesis of unsymmetrical phenylurea derivatives via oxidative cross coupling of aryl formamides with amines under metal-free conditions

2015 ◽  
Vol 39 (2) ◽  
pp. 805-809 ◽  
Author(s):  
Nagireddy Veera Reddy ◽  
Pailla Santhosh Kumar ◽  
Peddi Sudhir Reddy ◽  
Mannepalli Lakshmi Kantam ◽  
Kallu Rajender Reddy
Keyword(s):  
Cross Coupling ◽  
Hypervalent Iodine ◽  
Direct Transformation ◽  
Metal Free

A direct transformation of N-aryl formamides to the corresponding phenylurea derivatives via the formation of isocyanate intermediates is achieved in good yields using hypervalent iodine reagents as external oxidants.

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