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7. Demystifying the recent photochemical and electrochemical strategies in installing the magic methyl group: a comprehensive overview.

Author

Liao, Feiyang, Wei, Zenghui, Guan, Yunhao, Zhuang, Zhe, Xu, Kun, and Tan, Jiajing

Subjects
METHYL groups, DRUG discovery, ORGANIC chemistry, MAGIC, SUSTAINABLE development
Abstract

The strategic installation of the "magic methyl" group at a certain location in lead compounds has become an important tool for medicinal chemists in the field of drug discovery. Both photochemistry and electrochemistry have witnessed an explosive resurgence in recent years and emerged as a cornerstone of modern organic chemistry. In this review, we conducted an extensive data mining of the literature and provide a comprehensive overview of the recent advancements in utilizing green photochemical and electrochemical methodologies for the incorporation of methyl groups, with specific emphasis on the methyl source, design strategies and reaction mechanisms. These research developments provide sustainable and broadly applicable tools to develop valuable methylated products with major prospects for the pharmaceutical industry. In addition, their applications in the late-stage functionalization of bioactive compounds are also demonstrated. [ABSTRACT FROM AUTHOR]

Published
2024
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9. Contributors

Author

Biju, Akkattu T., primary, Chen, Jian, additional, Deswal, Shiksha, additional, Guin, Avishek, additional, Hamura, Toshiyuki, additional, Ikawa, Takashi, additional, Jiang, Xuefeng, additional, Tan, Jiajing, additional, Tanaka, Hideya, additional, Yoshida, Hiroto, additional, and Zhu, Guohao, additional

Published
2022
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15. Ethynyl‐B(dan) in [3+2] Cycloaddition and Larock Indole Synthesis: Synthesis of Stable Boron‐Containing Heteroaromatic Compounds.

Author

Li, Jialun, Tanaka, Hideya, Imagawa, Taiki, Tsushima, Takumi, Nakamoto, Masaaki, Tan, Jiajing, and Yoshida, Hiroto

Subjects
RING formation (Chemistry), INDOLE, LEWIS acidity, BENZOFURAN, TRIAZOLES, NITRILE oxides
Abstract

The cycloaddition of nitrile oxides with ethynyl‐B(dan) (dan=naphthalene‐1,8‐diaminato) allowed the facile preparation of diverse isoxazolyl‐B(dan) compounds, all of which displayed excellent protodeborylation‐resistant properties. The dan‐installation on the boron center proves vital to the high stability of the products as well as the perfect regioselectivity arising from hydrogen bond‐directed orientation in the cycloaddition. The diminished boron‐Lewis acidity of ethynyl‐B(dan) also renders it amenable to azide‐alkyne cycloaddition, Larock indole synthesis and related heteroannulations. The obtained boron‐containing triazole, indoles, benzofuran and indenone exhibit sufficient resistance toward protodeborylation. Despite the commonly accepted transmetalation‐inactive property derived from the diminished Lewis acidity, the synthesized heteroaryl‐B(dan) compound was still found to be convertible to the oligoarene via sequential Suzuki‐Miyaura coupling. [ABSTRACT FROM AUTHOR]

Published
2024
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18. When Aryne Chemistry Meets Organosulfur Compounds.

Author

Tan, Jiajing, Feng, Xiaoying, Fan, Rong, Zhuang, Zhe, and Guo, Yifeng

Subjects
*ARYNE, *SIGMATROPIC rearrangements, *RING-opening reactions, *ZWITTERIONS, *ARYLATION, *SULFIDES, *ORGANOSULFUR compounds
Abstract

This article explores the field of organosulfur chemistry and its applications in various industries. The authors specifically discuss their research on aryne chemistry and its interaction with organosulfur compounds. They detail their efforts in developing synthetic methodologies using sulfonium zwitterions and the unique reactivities of the resulting S(IV) intermediates. The article highlights their recent achievements in sigmatropic rearrangement, ring-opening reactions of cyclic sulfides, and selective arylation of thio-oxindoles. The authors aim to advance zwitterion chemistry and expand its applications through selectivity control and diversity-oriented synthesis. [Extracted from the article]

Published
2023
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26. Recent Advances in Construction of C(sp2)–O Bonds via Aryne Participated Multicomponent Coupling Reactions.

Author

Zhang, Ruirui, Peng, Xia, and Tan, Jiajing

Subjects
ARYNE, PHENYL ethers, STRUCTURAL components, ETHER derivatives
Abstract

Aryne chemistry is a powerful synthetic technique that forms new bonds to aromatic rings. The recent resurgence of aryne-based multicomponent coupling strategies has led to an influx of methodologies for the mild synthesis of arene derivatives. In particular, these innovative discoveries broaden and streamline approaches toward phenol ether motifs, which are a prevalent structural component across a broad range of chemistry related research fields. Herein, this review aims to provide a comprehensive overview of the recent progress in the construction of C(sp2)–O bonds via aryne-induced multicomponent reactions. Special attention has been paid to reaction design and mechanistic pathways. 1 Introduction 2 Insertion-Based MCRs 3 Nucleophilic-Addition-Based MCRs 4 Cycloaddition-Based MCRs 5 Summary [ABSTRACT FROM AUTHOR]

Published
2022
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39. Simultaneous determination of interfacial molarities of an alcohol, bromide ion, and water during an alcohol induced microstructural transition: the difference between medium and long chain alcohols

Author

Yao, Kaixin, primary, Sun, Lijie, additional, Ding, Xiaoxuan, additional, Wang, Yuzhao, additional, Liu, Tianze, additional, Liu, Changyao, additional, Tan, Jiajing, additional, Zhao, Li, additional, Xu, Baocai, additional, and Romsted, Larry, additional

Published
2020
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50. Reactions of Organophosphorus Compounds with Arynes: Reactivity and Mechanism.

Author

Chen, Jian, Fan, Rong, Liu, Zhijian, and Tan, Jiajing

Subjects
ORGANOPHOSPHORUS compounds, PHOSPHORUS compounds, AROMATIC compounds, PHARMACEUTICAL chemistry, VALENCE (Chemistry), ARYNE
Abstract

Aryl phosphorus compounds have found versatile applications in materials, medicinal and synthetic chemistry. As a powerful tool, aryne chemistry has been widely utilized in constructing aryl C−P bonds under mild conditions; this has enabled facile access to a variety of structurally diverse aryl–phosphorus compounds with good efficiency. The present review aims to offer a comprehensive overview of the chemistry between arynes and organophosphorus compounds, with emphasis placed on reactivity modes and mechanistic aspects. According to the valency of phosphorus atoms, this paper is divided into two main sections, reactions of arynes with organophosphorus(III) compounds and those with organophosphorus(V) compounds. [ABSTRACT FROM AUTHOR]

Published
2021
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