☆ 4.8 Article

Cu-Catalyzed Deoxygenative C2-Sulfonylation Reaction of Quinoline N-Oxides with Sodium Sulfinate

ORGANIC LETTERS (2016)

Journal

ORGANIC LETTERS

Volume 18, Issue 16, Pages 4144-4147

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/acs.orglett.6b02289

Keywords

-

Categories

Chemistry, Organic

Funding

National Natural Science Foundation of China [21472082]

Ask authors/readers for more resources

Protocol

Community support

Reagent

Community support

Abstract

An unexpected Cu-catalyzed deoxygenative Cu-sulfonylation reaction of quinoline N-oxides in the presence of radical initiator K2S2O8 was developed that used sodium sulfinate as a sulfonyl coupling partner. The mechanism studies indicate that the reaction proceeds via,Minisci-like radical coupling step to give sulfonylated quinoline with good chemical yields.

Authors

I am an author on this paper

Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.8

Not enough ratings

Secondary Ratings

Novelty

-

Significance

-

Scientific rigor

-

Rate this paper

Recommended

Article Chemistry, Organic

Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolinesY

Geetanjali S. Sontakke, Rahul K. Shukla, Chandra M. R. Volla

Summary: This study presents a metal-and additive-free, efficient synthesis method for synthesizing alpha-triazolylquinoline derivatives, with good regioselectivity and excellent yields under mild reaction conditions. Additionally, gram-scale and one-pot synthesis demonstrated the efficacy and simplicity of the developed protocol, showing compatibility for late-stage modification of natural products.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Electrochemical Oxidative C(sp3)-H Sulfonylation of Xanthenes with Sodium Sulfinates

Wei Bin, Zhou Zilong, Qin Jinghao, Yan Zeyu, Guo Jiacheng, Lei Shu, Xie Yexiang, Ouyang Xuanhui, Song Renjie

Summary: The direct electrochemical sulfonylation of C(sp(3))-H bonds of xanthenes with sodium sulfinates was investigated. A variety of 9-(arylsulfonyl)-9H-xanthenes and 9-(alkylsulfonyl)-9H-xanthenes were synthesized in one step at room temperature. The reaction proceeded through a radical pathway and resulted in the formation of a new C-S bond. The strategy offers significant advantages such as being transition metal- and additional oxidant-free, mild reaction conditions, operational simplicity, broad substrate scope, and excellent functional group tolerance.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2023)

Add to Collection

Article Chemistry, Applied

Iodine Catalyzed C2-H Formamidation of Quinoline N-Oxides using Isocyanides: A Metal-Free Approach

Naveenkumar Anugu, Sanjeeva Thunga, Sivaparwathi Golla, Hari Prasad Kokatla

Summary: A new regioselective method has been developed for the insertion of isocyanide into the C2-H position of quinoline N-oxides catalyzed by molecular iodine, resulting in rapid access to quinoline 2-formamides with exceptional functional group tolerance, broad substrate scope, and 100% atom-economy. This metal-free reaction has synthesized a library of 33 N-(2-quinolinyl)formamides, which may have potential applications in pharmaceuticals and synthetic chemistry.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Add to Collection

Article Chemistry, Organic

Synthesis of Quinoline Silyloxymethylsulfones as Intermediates to Sulfonyl Derivatives

Twinkle I. Patel, Ramkrishna Laha, Matthew J. Moschitto

Summary: In this study, a selective method for the synthesis of C2-substituted sulfones using sodium tert-butyldimethyl silyloxymethylsulfinate and quinoline N-oxides was reported. This scalable transformation has broad applicability to various quinoline and isoquinoline functionalities.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Bottom-Up Preparation of Twisted Graphene Nanoribbons by Cu-Catalyzed Deoxygenative Coupling

Yuan Gao, Xinqiang Hua, Wei Jiang, Chun-Lin Sun, Chengshan Yuan, Zitong Liu, Hao-Li Zhang, Xiangfeng Shao

Summary: Graphene nanoribbons (GNRs) show promise in organic optoelectronic materials. This study focuses on fully armchair-edged GNRs (AGNRs) and reveals their highly twisted pi-scaffolds and enhanced fluorescence performance.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Copper-catalyzed C2 alkenylation of pyridine-N-oxides with alkynes

Shuxia Wang, Lei Sun, Minghui Gao, Qin Jiang, Weiming Hu, Yaya Liu, Chuanzhou Tao

Summary: A general and expedient method has been disclosed for constructing the scaffolds of 2-alkenylpyridines through copper-catalyzed C2 alkenylation of pyridine-N-oxides with alkynes. This protocol demonstrates operational simplicity, good functional group compatibility, and broad substrate scope.

CHEMICAL COMMUNICATIONS (2022)

Add to Collection

Article Chemistry, Organic

N-Oxide-Induced Ugi Reaction: A Rapid Access to Quinoline-C2-amino Amides via Deoxygenative C(sp2)-H Functionalization

Naveenkumar Anugu, Sanjeeva Thunga, Soumya Poshala, Hari Prasad Kokatla

Summary: A logic-based approach using quinoline N-oxides as a replacement for the carboxylic acid component in the Ugi reaction has been developed. The unique reactivity of N-oxides enables the efficient synthesis of biologically active compounds.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Add to Collection

Article Chemistry, Organic

Palladium-Catalyzed Sulfinylation of Aryl- and Alkenylborons with Sulfinate Esters

Minori Suzuki, Kazuya Kanemoto, Yu Nakamura, Takamitsu Hosoya, Suguru Yoshida

Summary: An efficient and direct sulfinylation of organoborons catalyzed by palladium has been revealed, providing a broad range of sulfoxides. Various organosulfur compounds with oxidizable functional groups were successfully prepared through sulfoxide synthesis.

ORGANIC LETTERS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Iron Single Atom Catalyzed Quinoline Synthesis

Zhongxin Chen, Jingting Song, Xinwen Peng, Shibo Xi, Jia Liu, Wenhui Zhou, Runlai Li, Rile Ge, Cuibo Liu, Haisen Xu, Xiaoxu Zhao, Haohan Li, Xin Zhou, Lu Wang, Xing Li, Linxin Zhong, Alexandre I. Rykov, Junhu Wang, Ming Joo Koh, Kian Ping Loh

Summary: The study focuses on the development of mechanically strong, hierarchically porous carbon plates for the immobilization of single-atom catalysts (SACs) to enhance catalytic activity and stability. The carbon-based SACs exhibit excellent activity and selectivity for the synthesis of a wide assortment of quinolines through a three-component oxidative cyclization. The strategy is also applicable to challenging reactions such as the deuteration of quinolines at the fourth position.

ADVANCED MATERIALS (2021)

Add to Collection

Article Chemistry, Organic

Electrochemistry Enabled Nickel-Catalyzed Selective C-S Bond Coupling Reaction

Yang Wang, Feng Zhang, Yi Wang, Yi Pan

Summary: This work describes an electrochemical enabled nickel-catalyzed chemoselective C-S bond coupling protocol for the production of aryl sulfides and sulfones. By simply switching the nickel catalysts and electrodes, this electrochemical C-S bond coupling has demonstrated excellent redox activity, scalability, and sustainability. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Decatungstate-Catalyzed C(sp3)-H Sulfinylation: Rapid Access to Diverse Organosulfur Functionality

Patrick J. Sarver, Noah B. Bissonnette, David W. C. MacMillan

Summary: The study presents a method for converting strong, aliphatic C(sp(3))-H bonds into alkyl sulfinic acids using decatungstate photocatalysis, which can be applied to a variety of C(sp(3))-rich molecules for efficient synthesis of complex sulfur-containing compounds. Furthermore, the method demonstrates potential for divergent synthesis of pharmaceutically relevant molecules through diversification of the sulfinic acid products into various medicinally relevant functional groups.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Add to Collection

Article Chemistry, Organic

Cu-Catalyzed Decarboxylative Annulation of N-Phenylglycines with Maleimides: Synthesis of 1H-Pyrrolo[3,4-c]quinoline-1,3(2H)-diones

Kai-Hong Lv, Li Chen, Ke-hua Zhao, Jia-Ming Yang, Sheng-Jiao Yan

Summary: A novel protocol for the construction of functionalized PQLs from N-phenylglycines and maleimides was developed using a one-pot cascade reaction. The reaction proceeded through oxidative decarboxylation, 1,2-addition, intramolecular cyclization, tautomerization, and aromatization reactions. This protocol allows for the synthesis of functionalized PQLs in moderate-to-good yields, making it suitable for combinatorial and parallel syntheses.

JOURNAL OF ORGANIC CHEMISTRY (2023)

Add to Collection

Article Chemistry, Organic

Copper-catalyzed regioselective C2-H chlorination of indoles with para-toluenesulfonyl chloride

Xue-Hong Li, Guang-Chao Yang, Jun-Fang Gong, Mao-Ping Song

Summary: A copper-catalyzed, pyrimidine directed regioselective C-H chlorination of indoles has been developed. The reactions proceed smoothly with the presence of Cu(OAc)(2) as the catalyst and TsCl as the chlorine source, leading to the formation of C2-chlorinated indoles with structural diversity.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Add to Collection

Article Chemistry, Organic

Synthesis of Sulfonylated Cinchona Alkaloids via Zinc-Mediated Sulfonylation of the N-Oxides of the Quinoline Groups

Jie Zhou, Cheng-Yu Gu, Fu-She Han

Summary: This study presents a general and practical method for the synthesis of sulfonylated cinchona alkaloids via zinc-mediated nucleophilic aromatic substitution. The reaction yields high quantities of the corresponding sulfonylated products and can be scaled up to gram level.

SYNTHESIS-STUTTGART (2022)

Add to Collection

Article Chemistry, Applied

Photoredox and Copper-Catalyzed Sulfonylphosphorothiolation of Alkenes toward β-Sulfonyl Phosphorothioates

Pengbo Zhang, Wenwu Li, Xianglong Zhu, Ying Li, Xiangmei Zhao, Saige Shi, Fengxiang Zhu, Jinming Lin, Xia Gao

Summary: A photoredox and copper-catalyzed sulfonylphosphorothiolation of alkenes has been developed, allowing the synthesis of a wide range of decorated beta-sulfonyl phosphorothioates. The reaction shows good functional group tolerance and can be conveniently used for late-stage modification of bioactive molecules and gram-scale synthesis.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Add to Collection

Article Chemistry, Organic

Copper-Catalyzed Multicomponent Reaction of DABCO center dot(SO2)(2), Alcohols, and Aryl Diazoniums for the Synthesis of Sulfonic Esters

Yang Wang, Lingling Deng, Yu Deng, Jianlin Han

JOURNAL OF ORGANIC CHEMISTRY (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Efficient bluish green electroluminescence of iridium complexes with good electron mobility

Hua-Bo Han, Zheng-Guang Wu, You-Xuan Zheng

NEW JOURNAL OF CHEMISTRY (2018)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Efficient electroluminescence of bluish green iridium complexes with 2-(3,5-bis(trifluoromethyl) phenyl) pyrimidine and 2-(3,5-bis(trifluoromethyl) phenyl)-5-fluoropyrimidine as the main ligands

Hua-Bo Han, Zheng-Guang Wu, You-Xuan Zheng

INORGANIC CHEMISTRY FRONTIERS (2018)

Add to Collection

Article Chemistry, Applied

Synthesis of Chiral Sulfonyl Lactones via Copper-Catalyzed Asymmetric Radical Reaction of DABCO center dot(SO2)

Yang Wang, Lingling Deng, Jie Zhou, Xiaochen Wang, Haibo Mei, Jianlin Han, Yi Pan

ADVANCED SYNTHESIS & CATALYSIS (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Leaving Group Assisted Strategy for Photoinduced Fluoroalkylations Using N-Hydroxybenzimidoyl Chloride Esters

Weigang Zhang, Zhenlei Zou, Yuanheng Wang, Yi Wang, Yong Liang, Zhengguang Wu, Youxuan Zheng, Yi Pan

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Add to Collection

Article Chemistry, Applied

Green iridium complexes based on pyrimidine derivatives for efficient electroluminescence with EQE near 30%

Hua-Bo Han, Zhen-Long Tu, Zheng-Guang Wu, You-Xuan Zheng

DYES AND PIGMENTS (2019)

Add to Collection

Article Nanoscience & Nanotechnology

Fast Synthesis of Iridium(III) Complexes Incorporating a Bis(diphenylphorothioyl)amide Ligand for Efficient Pure Green OLEDs

Xiao Liang, Feng Zhang, Zhi-Ping Yan, Zheng-Guang Wu, Youxuan Zheng, Gang Cheng, Yi Wang, Jing-Lin Zuo, Yi Pan, Chi-Ming Che

ACS APPLIED MATERIALS & INTERFACES (2019)

Add to Collection

Article Chemistry, Organic

Electrochemically Promoted Fluoroalkylation-Distal Functionalization of Unactivated Alkenes

Zhenlei Zou, Weigang Zhang, Yang Wang, Lingyu Kong, Georgios Karotsis, Yi Wang, Yi Pan

ORGANIC LETTERS (2019)

Add to Collection

Article Chemistry, Physical

Electrochemically Promoted Nickel-Catalyzed Carbon-Sulfur Bond Formation

Yang Wang, Lingling Deng, Xiaochen Wang, Zhengguang Wu, Yi Wang, Yi Pan

ACS CATALYSIS (2019)

Add to Collection

Article Nanoscience & Nanotechnology

Pure Red Iridium(111) Complexes Possessing Good Electron Mobility with 1,5-Naphthyridin-4-ol Derivatives for High-Performance OLEDs with an EQE over 31%

Guang-Zhao Lu, Qi Zhu, Liang Liu, Zheng-Guang Wu, You-Xuan Zheng, Liang Zhou, Jing-Lin Zuo, Hongjie Zhang

ACS APPLIED MATERIALS & INTERFACES (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Configurationally Stable Platinahelicene Enantiomers for Efficient Circularly Polarized Phosphorescent Organic Light-Emitting Diodes

Zhi-Ping Yan, Xu-Feng Luo, Wei-Qiang Liu, Zheng-Guang Wu, Xiao Liang, Kang Liao, Yi Wang, You-Xuan Zheng, Liang Zhou, Jing-Lin Zuo, Yi Pan, Hongjie Zhang

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Add to Collection

Article Chemistry, Organic

Electrochemical Deoxygenative Thiolation of Preactivated Alcohols and Ketones

Feng Zhang, Yang Wang, Yi Wang, Yi Pan

Summary: This work describes a nickel-catalyzed deoxygenative thiolation of alcohols and ketones under mild conditions with electrochemical promotion. Graphene/nickel foam electrodes in an undivided cell exhibit excellent substrate tolerance and good chemical yields. Further investigation has been conducted to gain mechanistic insight into this electrochemical cross-coupling.

ORGANIC LETTERS (2021)

Add to Collection

Article Chemistry, Organic

Electrochemistry Enabled Nickel-Catalyzed Selective C-S Bond Coupling Reaction

Yang Wang, Feng Zhang, Yi Wang, Yi Pan

Summary: This work describes an electrochemical enabled nickel-catalyzed chemoselective C-S bond coupling protocol for the production of aryl sulfides and sulfones. By simply switching the nickel catalysts and electrodes, this electrochemical C-S bond coupling has demonstrated excellent redox activity, scalability, and sustainability. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

Add to Collection

Review Chemistry, Organic

Recent advances in electrochemical deoxygenation reactions of organic compounds

Yang Wang, Jia Xu, Yi Pan, Yi Wang

Summary: As abundant and recyclable industrial feedstock, alcohols and carboxylic acids have attracted great attention in medicinal chemistry and polymer chemistry. The use of electrosynthesis has proven to be an effective and mild way to achieve selective C-O cleavage of the hydroxyl group. In this review, recent advances in electrochemical deoxygenation reactions are summarized and categorized by different functionalities.

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

Add to Collection

Article Materials Science, Multidisciplinary

Highly efficient green and red electroluminescence with an extremely low efficiency roll-off based on iridium(iii) complexes containing a bis(diphenylphorothioyl)amide ancillary ligand

Xiao-Feng Ma, Jing-Cheng Xia, Zhi-Ping Yan, Xu-Feng Luo, Zheng-Guang Wu, You-Xuan Zheng, Wen-Wei Zhang

JOURNAL OF MATERIALS CHEMISTRY C (2019)

Add to Collection

No Data Available

© Peeref 2019-2024. All rights reserved.