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.

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.

UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

Synthesis ◽  
2022 ◽  
Author(s):  
Dishu Zeng ◽  
Tianbao Yang ◽  
Niu Tang ◽  
Wei Deng ◽  
Jiannan Xiang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Organic Synthesis ◽  
Efficient Method ◽  
Building Block ◽  
Room Temperature ◽  
Uv Light ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Plausible Mechanism ◽  
High Yields

A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

scholarly journals Copper-catalyzed N-alkylation of indoles by N-tosylhydrazones

RSC Advances ◽  
2017 ◽  
Vol 7 (45) ◽  
pp. 27974-27980 ◽  
Author(s):  
Li Ling ◽  
Jing Cao ◽  
Jianfeng Hu ◽  
Hao Zhang
Keyword(s):  
Efficient Method ◽  
Cross Coupling

An efficient method for direct N-alkylation of indoles via copper-catalyzed reductive cross coupling between N-tosylhydrazones and indoles has been developed.

Metallic salt-catalyzed direct indium insertion into alkyl iodides and their applications in cross-coupling reactions

2019 ◽  
Vol 6 (3) ◽  
pp. 313-318 ◽  
Author(s):  
Bing-Zhi Chen ◽  
Chuang-Xin Wang ◽  
Zhen-Hua Jing ◽  
Xue-Qiang Chu ◽  
Teck-Peng Loh ◽  
...  
Keyword(s):  
Efficient Method ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Esi Ms ◽  
Cross Coupling Reactions ◽  
Metallic Salt ◽  
Alkyl Iodides

An efficient method for the synthesis of alkyl indium reagents via an indium(iii) or lead(ii) halide-catalyzed direct insertion of indium into alkyl iodides is developed. NMR and ESI-MS analyses indicated the formation of a mixture of an alkyl indium dihalide (RInX2) and a dialkyl indium halide (R2InX).

Stereoretentive Suzuki–Miyaura and Kumada–Tamao–Corriu Cross-Couplings for Preparing (E)- and (Z)-Stereodefined, Fully Substituted α,β-Unsaturated Esters: Application for a Pharmacophore Synthesis

Synthesis ◽  
2018 ◽  
Vol 50 (23) ◽  
pp. 4659-4667 ◽  
Author(s):  
Yoo Tanabe ◽  
Yuka Sato ◽  
Yuichiro Ashida ◽  
Daisuke Yoshitake ◽  
Mayuko Hoshino ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Unsaturated Esters ◽  
Cross Coupling Reactions ◽  
Plausible Mechanism

Substrate-general stereocomplementary Suzuki–Miyaura (SM) cross-coupling and relevant Kumada–Tamao–Corriu (KTC) cross-coupling reactions for preparing (E)- and (Z)-stereodefined, fully substituted α,β-unsaturated esters are described. The SM cross-coupling reactions were performed under Pd(OAc)2/SPhos/iPr2NEt catalysis (24 examples, 66–99% yield). The KTC cross-coupling reactions were also performed under similar Pd(OAc)2/SPhos conditions (11 examples, 50–98% yield). Application to a useful pharmacophore containing a cyclopropane structure was investigated, wherein distinctive (E)- and (Z)-stereochemical difference between XPhos and SPhos was observed. A plausible mechanism for the stereoretention and stereoinversion cross-coupling reactions is proposed.

Dithienophosphole-based molecular electron acceptors constructed using direct (hetero)arylation cross-coupling methods

2018 ◽  
Vol 6 (8) ◽  
pp. 2148-2154 ◽  
Author(s):  
Thomas A. Welsh ◽  
Audrey Laventure ◽  
Thomas Baumgartner ◽  
Gregory C. Welch
Keyword(s):  
Building Block ◽  
Cross Coupling ◽  
Electron Acceptors ◽  
Bond Functionalization ◽  
Coupling Methods ◽  
Molecular Electron ◽  
End Caps

Herein we report on the first successful coupling of the dithienophosphole (S2PO) functional building block with three types of heteroaryl end caps using direct (hetero)arylation C–H bond functionalization methods.

Regiocontrolled functionalization of 2,3-dihalogenoimidazo[1,2-a]pyridines by Suzuki–Miyaura and Sonogashira cross-coupling reactions

2017 ◽  
Vol 15 (19) ◽  
pp. 4199-4204 ◽  
Author(s):  
P.-O. Delaye ◽  
M. Pénichon ◽  
H. Allouchi ◽  
C. Enguehard-Gueiffier ◽  
A. Gueiffier
Keyword(s):  
Efficient Method ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

An efficient method for regiocontrolled functionalization of 2,3-dihalogenoimidazo[1,2-a]pyridine was developed.

Sonogashira cross-coupling reaction with 4-[18F]fluoroiodobenzene for rapid 18F-labelling of peptides

2015 ◽  
Vol 51 (18) ◽  
pp. 3838-3841 ◽  
Author(s):  
Jenilee D. Way ◽  
Cody Bergman ◽  
Frank Wuest
Keyword(s):  
Efficient Method ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
Positron Emitter ◽  
18F Labelling

The study describes the Sonogashira cross-coupling reaction with 4-[18F]fluoroiodobenzene ([18F]FIB) as novel and efficient method for rapid labelling of peptides with the short-lived positron emitter fluorine-18.

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