☆ 4.8 Article

Rh(III)-Catalyzed Enaminone-Directed Alkenyl C-H Activation for the Synthesis of Salicylaldehydes

ORGANIC LETTERS (2018)

期刊

ORGANIC LETTERS

卷 20, 期 13, 页码 3996-3999

出版社

AMER CHEMICAL SOC

DOI: 10.1021/acs.orglett.8b01563

关键词

-

类别

Chemistry, Organic

资金

National Natural Science Foundation of China [21425415, 21774056]
National Basic Research Program of China [2015CB856303]

向作者/读者索取更多资源

Protocol

Reagent

摘要

A Rh(III)-catalyzed enaminone-directed alkenyl C-H coupling with alkynes for the synthesis of salicylaldehyde derivatives is reported. This represents a unique example of benzene ring framework formation through a transition-metal-catalyzed, directed C-H activation strategy. The two incorporated reactive functionalities, aldehyde and hydroxy groups, provide convenient synthetic handles for further structural elaboration.

作者

我是这篇论文的作者

点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.8

评分不足

次要评分

新颖性

-

重要性

-

科学严谨性

-

评价这篇论文

推荐

Article Chemistry, Multidisciplinary

CpIr(iii) and CpRh(iii)-catalyzed annulation of salicylaldehydes with fluorinated vinyl tosylates

Shuwen Zhao, Xiaojia Cai, Yuying Lu, Jinhui Hu, Zhuang Xiong, Jingwei Jin, Yin Li, Honggen Wang, Jia-Qiang Wu

Summary: A mild, selective, and redox-neutral C-H activation/annulation reaction of salicylaldehydes with fluorovinyl tosylates is reported. The use of monofluorovinyl tosylate leads to the synthesis of C2- and C3-substitution-free chromones, while difluorovinyl tosylate results in the construction of C2-fluoroalkoxy chromones. The reaction exhibits mild conditions and good functional-group tolerance.

CHEMICAL COMMUNICATIONS (2022)

添加到收藏夹

Article Chemistry, Applied

Indazolones Directed Rh(III)-Catalyzed C-H Amidation of Arenes

Shao-Yong Chen, Yi-Chuan Zheng, Xu-Ge Liu, Jia-Lin Song, Bing Shu, Tao Zheng, Lin Xiao, Shang-Shi Zhang, Hua Cao

Summary: The Cp*Rh(III)-catalyzed indazolone-directed C-H bond amidation of arenes has been achieved using sulfonyl azide agents and dioxazolones as nitrogen source. This protocol showcases mild conditions, broad substrate scope, and high functional group compatibility. Additionally, it has been successfully applied for late-stage modifications of complex drug structures, and preliminary mechanistic investigation and an exploratory reaction mechanism have been proposed.

ADVANCED SYNTHESIS & CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Physical

Intramolecular Alkene-Alkene Coupling via Rh(III)-Catalyzed Alkenyl sp2 C-H Functionalization: Divergent Pathways to Indene or α-Naphthol Derivatives

Manikantha Maraswami, Thomas Diggins, Jeffrey Goh, Raymond Tio, Wan Qing Renee Ong, Hajime Hirao, Teck-Peng Loh

Summary: This study presents a highly selective synthesis method for indene or 1-naphthol derivatives through intramolecular alkene-alkene cross-coupling, which works with different alkene pairs to give products in good to satisfactory yields. The indene products of the reaction allow further derivatization, and the reaction pathway is dependent on alkene functionalities.

ACS CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Organic

Practical synthesis of isocoumarins via Rh(III)-catalyzed C-H activation/annulation cascade

Qian-Ci Gao, Yi-Fei Li, Jun Xuan, Xiao-Qiang Hu

Summary: Herein, we report an unprecedented Rh(III)-catalyzed C-H activation/annulation cascade of readily available enaminones with iodonium ylides towards the convenient synthesis of isocoumarins. This coupling system proceeds in useful chemical yields (up to 93%) via a cascade C-H activation, Rh-carbenoid migratory insertion and acid-promoted intramolecular annulation. The success of gram-scale reaction and diverse functionalization of isocoumarins demonstrated the synthetic utility of this protocol.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Organic

Thioether-directed Rh(iii)-catalyzed peri-selective acyloxylation of arenes

Hui Xie, Jia-Lin Song, Chun-Yong Jiang, Yan-Xia Huang, Jun-Yi Zeng, Xu-Ge Liu, Shang-Shi Zhang, Fan Yang

Summary: This new method of thioether-directed acyloxylation of arenes through Cp*Rh(iii)-catalyzed C-H activation shows high functional group compatibility and broad substrate scope. Preliminary mechanistic studies have been conducted, proposing a tentative reaction mechanism for this novel process.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Applied

Rh(III)-Catalyzed Direct ortho Alkylation of Carbazoles with Nitroalkenes

Liming Zhang, Ru Zhao, Chunhui Liu, Zhaoyang Li, Jun-Long Niu, Hao-Ran Yang, Lijun Gao, Shuang-Liang Liu, Liming Zhou

Summary: The Rh(III)-catalyzed ortho alkylation of N-pyridylcarbazoles with nitroalkenes has been developed for the synthesis of a wide range of 2-(2nitroalkyl)carbazoles. Aromatic and aliphatic nitroalkenes both successfully participated in this alkylation reaction. The protocol also worked well with an indoline based substrate. Derivatization of the representative nitroalkane product was described.

ADVANCED SYNTHESIS & CATALYSIS (2023)

添加到收藏夹

Article Chemistry, Organic

Cp*Rh(III)-Catalyzed ortho-Alkylation/Alkenylation of Nitroarenes

Lin Xiao, Xu-Ge Liu, Mei-Zhu Bao, Jia-Lin Song, Shao-Yong Chen, Yi-Chuan Zheng, Yan-Zhi Liu, Shang-Shi Zhang

Summary: The Cp*Rh(III)-catalyzed nitro-directed C-H alkylation/alkenylation of nitroarenes has been reported for the first time. This method exhibits high efficiency, broad substrate scope, and good functional group compatibility. Gram-scale experiments and synthetic applications confirmed the practicality of this method. Furthermore, preliminary mechanistic investigations consistently indicated that C-H bond cleavage is the rate-limiting step.

ORGANIC LETTERS (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Cp*Rh(iii)-catalyzed regioselective cyclization of aromatic amides with allenes

Jing Liu, Deng-Yin Liu, Qian Yang, Yao-Fu Zeng, Xiao-Li Wang, Peng-Fei Wang, Yu-Jun Ruan, Miao-Miao Wen, Shang-Shi Zhang, Li-da Du, Xu-Ge Liu

Summary: A new catalytic system using allenyl derivatives bearing a directing-group assistant as a reaction promoter has been developed for the regioselective cyclization reaction of aromatic amides with allenes. This reaction exhibits mild reaction conditions, a broad substrate scope, and high functional-group compatibility, leading to the synthesis of valuable compounds containing isoquinolinone and pyrimido[1,6-a]indol-1(2H)-one skeletons.

CHEMICAL COMMUNICATIONS (2023)

添加到收藏夹

Article Chemistry, Organic

Rh(III)-Catalyzed Dienylation and Cyclopropylation of 1,2,3-Benzotriazinones with Alkylidenecyclopropanes

Yan-Zhi Liu, Yao-Fu Zeng, Jiaohang Wei, Lin Xiao, Bing Shu, Jia-Lin Song, Wen-Xuan Zou, Dan-Ting Shen, Shao-Yong Chen, Yi-Chuan Zheng, Shang-Shi Zhang

Summary: Rh(III)-catalyzed dienylation and cyclopropylation of 1,2,3-benzotriazinones with alkylidenecyclopropanes (ACPs) have been achieved, which is distinct from previous reports. The intact triazinone ring in this C-H bond functionalization reaction was maintained. Additionally, denitrogenative cyclopropylation could also be realized by altering the reaction temperature. This protocol features high E selectivity, broad substrate scope, and diverse product structures.

ORGANIC LETTERS (2023)

添加到收藏夹

Article Chemistry, Organic

Rh(III)-Catalyzed Alkylation of 8-Methylquinolines with Oxabenzonorbornadienes

Rohit Sarthi, Rohit Kumar, Tamanna Sharma, Upendra Sharma

Summary: In this study, a concise Rh(III)-catalyzed C(sp3)-H alkylation of 8-methylquinolines with oxabenzonorbornadiene scaffolds and other strained olefins was presented. The developed catalytic methodology exhibits key features such as the retention of the oxabenzonorbornadiene skeleton, broad substrate scope, and wide-ranging functional group tolerance. Mechanistic studies revealed that the reaction proceeds through a non-radical pathway, with the five membered rhodacycle serving as the key intermediate. This is the first report on the C(sp3)-H alkylation of 8-methylquinolines with strained oxabenzonorbornadiene scaffolds (with ring retention).

ORGANIC LETTERS (2023)

添加到收藏夹

Article Chemistry, Organic

Rh(III)-Catalyzed Selective C7 Halogenation of Indolines

Manisha, Shiv Shankar Gupta, Ankit Kumar Dhiman, Upendra Sharma

Summary: An efficient Rh-catalyzed method has been developed for selective C7 halogenation of N-pyrimidyl indolines, producing corresponding halides in good to excellent yields. The strategy demonstrates broad substrate scope, excellent regioselectivity for C7 functionalization of indolines, and feasibility at gram scale level. Various control experiments were conducted to understand the reaction pathway, and the applicability of the methodology was demonstrated by synthesis of indoles and post-transformation of the C7 halogenated indolines into different valuable molecules.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Rh(iii)-Catalyzed mild straightforward synthesis of quinoline-braced cyclophane macrocycles via migratory insertion

Bidhan Ghosh, Satabdi Bera, Pintu Ghosh, Rajarshi Samanta

Summary: An efficient Rh(iii)-catalyzed strategy has been developed for the synthesis of quinoline braced cyclophane macrocycles via methyl (sp(3)) C-H functionalization, which is mild, simple, regioselective, and tolerates various functional groups with different ring sizes. The method involves C8-methyl metalation, metal-carbene formation, and migratory insertion, with high dilution not necessary and nitrogen being the only byproduct. Preliminary investigation suggests that the C-H metalation step is the rate-determining step.

CHEMICAL COMMUNICATIONS (2021)

添加到收藏夹

Article Chemistry, Organic

Synthesis of Indole-Substituted Trifluoromethyl Sulfonium Ylides by Cp*Rh(III)-Catalyzed Diazo-carbenoid Addition to Trifl uoromethylthioether

Shao-Yong Chen, Yi-Chuan Zheng, Xu-Ge Liu, Jia-Lin Song, Lin Xiao, Shang-Shi Zhang

Summary: The indole-substituted trifluoromethyl sulfonium ylide was synthesized via the Cp*Rh(III)-catalyzed addition of diazocarbenoid to trifluoromethylthioether, and it represents the first example of an Rh(III)-catalyzed diazo-carbenoid addition reaction with trifluoromethylthioether. Several types of indole-substituted trifluoromethyl sulfonium ylide were prepared using mild reaction conditions. The method demonstrated high compatibility with functional groups and a wide substrate scope. Furthermore, it was found to be complementary to the method previously disclosed using a Rh(II) catalyst.

JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

A hydrazine-directed Rh(iii) catalyzed (4+2) annulation with sulfoxonium ylides: synthesis and photophysical properties of dihydrocinnolines

Pothapragada S. K. Prabhakar Ganesh, Perumal Muthuraja, Purushothaman Gopinath

Summary: This report demonstrates a hydrazine-directed, Rh(iii) catalyzed (4+2) annulation reaction using sulfoxonium ylides as a safe carbene precursor. The reaction exhibits excellent functional group tolerance, broad substrate scope, scalability, and site selectivity. Additionally, photophysical studies suggest that some compounds formed in this reaction possess interesting fluorescence properties.

CHEMICAL COMMUNICATIONS (2022)

添加到收藏夹

Article Chemistry, Organic

Multiple Reaction Pathways of Eight-Membered Rhodacycles in Rh-Catalyzed Annulations of 2-Alkenyl Phenols/Anilides with Alkynes

Tao Liu, Lingli Han, Jing Zhang, Gang Lu

Summary: Density functional theory calculations were used to investigate the competing pathways of rhodacycle intermediates in Rh(III)-catalyzed annulations of 2-alkenyl phenols and 2-alkenyl anilides with alkynes. The results reveal that the multiple pathways of eight-membered rhodacycles can be subtly tuned to give specific cyclic products. The formation of different cyclic products from 2-alkenyl phenols and 2-alkenyl anilides is governed by different pathways involving the dissociation of Rh-O bond and intramolecular olefin migratory insertion, respectively.

JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Applied

Platinum-Catalyzed Tandem Cyclization Reaction to Multiply Substituted Indolines under Microwave-Assisted Conditions

Can-Liang Ma, Xiao-Long Yu, Xiao-Long Zhu, Yong-Zhou Hu, Xiao-Wu Dong, Bin Tan, Xin-Yuan Liu

ADVANCED SYNTHESIS & CATALYSIS (2015)

添加到收藏夹

Article Chemistry, Organic

Oxadiazolone-Enabled Synthesis of Primary Azaaromatic Amines

Xiaolong Yu, Kehao Chen, Fan Yang, Shanke Zha, Jin Zhu

ORGANIC LETTERS (2016)

添加到收藏夹

Article Chemistry, Physical

Counteranion-Controlled Unprecedented Diastereo- and Enantioselective Tandem Formal Povarov Reaction for Construction of Bioactive Octahydro-Dipyrroloquinolines

Xiao-Long Yu, Liping Kuang, Su Chen, Xiao-Long Zhu, Zhong-Liang Li, Bin Tan, Xin-Yuan Liu

ACS CATALYSIS (2016)

添加到收藏夹

Article Chemistry, Organic

Gold-catalyzed tandem synthesis of bioactive spiro-dipyrroloquinolines and its application in the one-step synthesis of incargranine B aglycone and seneciobipyrrolidine (I)

Can-Liang Ma, Xiao-Hua Li, Xiao-Long Yu, Xiao-Long Zhu, Yong-Zhou Hu, Xiao-Wu Dong, Bin Tan, Xin-Yuan Liu

ORGANIC CHEMISTRY FRONTIERS (2016)

添加到收藏夹

Article Chemistry, Organic

Direct Access to Cobaltacycles via C-H Activation: N-Chloroamide-Enabled Room-Temperature Synthesis of Heterocycles

Xiaolong Yu, Kehao Chen, Shan Guo, Pengfei Shi, Chao Song, Jin Zhu

ORGANIC LETTERS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of 2,5-disubstituted oxazoles via cobalt(III)-catalyzed cross-coupling of N-pivaloyloxyamides and alkynes

Xiaolong Yu, Kehao Chen, Qi Wang, Wenjing Zhang, Jin Zhu

CHEMICAL COMMUNICATIONS (2018)

添加到收藏夹

Article Chemistry, Organic

Co(III)-Catalyzed N-chloroamide-directed C-H activation for 3,4-dihydroisoquinolone synthesis

Xiaolong Yu, Kehao Chen, Qi Wang, Wenjing Zhang, Jin Zhu

ORGANIC CHEMISTRY FRONTIERS (2018)

添加到收藏夹

Article Chemistry, Organic

Nickel-Catalyzed Reductive Cross-Coupling of Unactivated Alkyl Halides

Xiaolong Yu, Tao Yang, Shulin Wang, Hailiang Xu, Hegui Gong

ORGANIC LETTERS (2011)

添加到收藏夹

Article Chemistry, Organic

Facile synthesis of salmochelin S1, S2, MGE, DGE, and TGE

Xiaolong Yu, Yijing Dai, Tao Yang, Michel R. Gagne, Hegui Gong

TETRAHEDRON (2011)

添加到收藏夹

Article Chemistry, Physical

Site-selective alkene borylation enabled by synergistic hydrometallation and borometallation

Xiaolong Yu, Haonan Zhao, Shibo Xi, Zhongxin Chen, Xiaowei Wang, Lin Wang, Leroy Qi Hao Lin, Kian Ping Loh, Ming Joo Koh

NATURE CATALYSIS (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Iron-Catalyzed Regioselective Alkenylboration of Olefins

Xiaolong Yu, Hongling Zheng, Haonan Zhao, Boon Chong Lee, Ming Joo Koh

Summary: A novel iron-catalyzed three-component synthesis method has been developed for the regioselective union of bis(pinacolato)diboron, an alkenyl halide, and an olefin to produce homoallylic boronates. The reaction can generate products with tertiary or quaternary carbon centers in up to 87% yield as single regioisomers with complete retention of the olefin stereochemistry. Selective formation of trisubstituted E-alkenylboronates from cyclopropylidene-containing substrates was also observed, revealing unique reaction attributes distinct from previously reported pathways.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Iron-Catalyzed Tunable and Site-Selective Olefin Transposition

Xiaolong Yu, Haonan Zhao, Ping Li, Ming Joo Koh

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Effect of solvation on the aggregation-induced luminescence of tetraphenylethene derivatives

Hui Yao, Meijuan Zhou, Xiaolong Yu, Ming Bai

Summary: By controlling the aggregation patterns through preferential solvation, a relatively stable non-emission aggregate with ultrasound-responsive emission properties of the compound TPE-(alpha-NH2)(2) can be synthesized in a water-THF mixture (f(w) = 90%).

CHEMICAL COMMUNICATIONS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Associative Covalent Relay: An Oxadiazolone Strategy for Rhodium(III)-Catalyzed Synthesis of Primary Pyridinylamines

Xiaolong Yu, Kehao Chen, Qi Wang, Shan Guo, Shanke Zha, Jin Zhu

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

添加到收藏夹

暂无数据

© Peeref 2019-2024. All rights reserved.