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.

An efficient method for the synthesis of 2-pyridones via C–H bond functionalization

2020 ◽  
Vol 56 (95) ◽  
pp. 15020-15023
Author(s):  
Shuguang Zhou ◽  
Duan-Yang Liu ◽  
Suo Wang ◽  
Jie-Sheng Tian ◽  
Teck-Peng Loh
Keyword(s):  
Efficient Method ◽  
Cross Coupling ◽  
Bond Functionalization ◽  
Plausible Mechanism

N-Substituted 2-pyridones are installed through the RhIII-catalyzed formal [3+3] annulation of enaminones with acrylates. Control and deuterated experiments led to a plausible mechanism involving C(sp2)–H bond cross-coupling and aminolysis cyclization.

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 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.

Transition-metal-free cross-coupling of thioethers with aryl(cyano)iodonium triflates: a facile and efficient method for the one-pot synthesis of thiocyanates

2015 ◽  
Vol 51 (33) ◽  
pp. 7180-7183 ◽  
Author(s):  
Dan Zhu ◽  
Denghu Chang ◽  
Lei Shi
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Bond Cleavage ◽  
Cross Coupling ◽  
One Pot ◽  
Metal Free ◽  
One Pot Synthesis ◽  
One Step ◽  
The One

A novel transition-metal-free method for the one-step synthesis of thiocyanates via the C–S bond cleavage of readily available thioethers was developed.

Transition-Metal-Free Aerobic Oxidative Cross-Coupling of Indoles with Arylidenemalononitriles

Synlett ◽  
2019 ◽  
Vol 31 (02) ◽  
pp. 194-198
Author(s):  
Aizhen Yang ◽  
Zheng Li
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Cross Coupling ◽  
Transition Metal Catalysts ◽  
High Yield ◽  
Atom Economy ◽  
Direct Construction ◽  
Organometallic Reagents ◽  
Metal Free ◽  
Mild Conditions

An efficient method for the direct construction of C(sp2)–C(sp2) bonds by aerobic oxidative cross-coupling of indoles with arylidenemalononitriles is described. Various [aryl(1H-indol-3-yl)methylene]malononitriles were efficiently synthesized by using air as an oxidant under mild conditions. The salient features for this protocol are no transition-metal catalysts, no organometallic reagents, high atom economy, high yield, mild conditions, and simple workup procedures.

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.

Transition-metal-free direct perfluoroalkylation of quinoline amides at C5 position through radical cross-coupling under mild conditions

2017 ◽  
Vol 4 (6) ◽  
pp. 1116-1120 ◽  
Author(s):  
Jun Xu ◽  
Li Qiao ◽  
Beibei Ying ◽  
Xiaolei Zhu ◽  
Chao Shen ◽  
...  
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Cross Coupling ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Low Energy ◽  
Metal Free ◽  
Mild Conditions

A simple low-energy and efficient method is established for the synthesis of C5-selective perfluoroalkylation quinolines in the absence of any transition metal catalysts.

Metal-free synthesis of gem-silylboronate esters and their Pd(0)-catalyzed cross-coupling with aryliodides

2019 ◽  
Vol 17 (23) ◽  
pp. 5714-5724 ◽  
Author(s):  
Chaoqiang Wu ◽  
Zhicheng Bao ◽  
Xing Xu ◽  
Jianbo Wang
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Cross Coupling ◽  
Metal Free ◽  
Arylboronic Acids

An efficient method for the synthesis of gem-silylboronate esters based on transition-metal-free reaction of arylboronic acids and trimethylsilyldiazomethane is developed, and Suzuki–Miyaura cross-coupling of gem-silylboronate esters with aryliodides is described.

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