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Divergent synthesis of aryl amines and dihydroquinazolinones via electrochemistry-enabled rhodium-catalyzed C–H functionalization

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中国科学:化学英文版 2023年第10期66卷 2863-2870页

作者： Yi-Kang Xing Zhen-Hua Wang Ping Fang Cong Ma Tian-Sheng Mei State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesShanghai 200032China

electrochemistry-enabled rhodium-catalyzed C–H amination and amination cyclization of arene assisted by a weakly coordinating amide have been reported. Additionally, aryl amines and dihydroquinazolinones could be obtained selectively by controlling the electric current. Mechanistic studies suggested that the amination reaction likely involves an electrochemical oxidation-induced reductive elimination of a high valent rhodium intermediate, which led to the amination reaction even proceeding smoothly at room temperature.

关键词： organic electrochemistry rhodium catalysis C-H functionalization divergent synthesis

Recent Advances in Electrochemical Oxidation to Construct C–O Bonds

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Transactions of Tianjin University 2022年第6期28卷 482-505页

作者： Lei Zhan Wan-Jie Wei Cai-Nai Jiang Lei Gao Xian-Li Ma Guangxi Key Laboratory of Drug Discovery and Optimization Guangxi Engineering Research Center for Pharmaceutical Molecular Screening and Druggability EvaluationSchool of PharmacyGuilin Medical UniversityGuilin 541004China

C–O bonds are widely found in pharmaceuticals and natural products and have various pharmacological activities.Therefore,developing eff ective strategies for constructing compounds containing C–O bonds has become a research hotspot among chemists.organic electrochemical synthesis is a green,mild,and effi cient strategy that shows great potential in the synthesis of compounds containing C–O bonds.This review introduces the reactions of compounds containing C–O bonds recently constructed by electrochemical methods and expounds the corresponding reaction mechanism to provide a reference for applying such reactions in organic synthesis.

关键词： organic electrochemistry C–O bond Green synthesis

Electrochemical Rhodium-Catalyzed Enantioselective C–H Annulation with Alkynes

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CCS Chemistry 2022年第9期4卷 3181-3189页

作者： Yuan-Qiong Huang Zhi-Jie Wu Li Zhu Qing Gu Xiaojie Lu Shu-Li You Tian-Sheng Mei State Key Laboratory of Organometallic Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032 State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of SciencesPudongShanghai 201203

The synergistic use of transition metal catalysis and electrochemistry is an attractive strategy for oxidative site-selective C–H functionalization since the use of stoichiometric chemical oxidants can be avoided and novel reactivity can be achieved.However,metalcatalyzed electrochemical C–H functionalization is mainly limited to arene C(sp^(2))–Hfunctionalization,and enantioselective C–H functionalization is uncommon and remains challenging.

关键词： organic electrochemistry enantioselective C–H annulation rhodium catalysis chiral spiropyrazolones C–H functionalization

平行成对电解促进的不对称催化:同时合成醛/芳基溴化物和手性醇

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科学通报:英文版 2023年第18期68卷 2033-2041,M0003,M0004页

作者：孙冰王振华王运召顾玉诚马聪梅天胜 State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032China Syngenta Jealott’s Hill International Research CentreBerkshire RE426EYUK

金属催化的不对称电还原偶联已成为有机合成的强有力工具,但是这类反应通常需要牺牲试剂或者牺牲阳极来获得电中性。同时利用阳极和阴极作为工作电极可以很好地解决该问题,然而也面临着诸多挑战:(1)完美匹配阳极氧化和阴极还原反应的电... 详细信息

金属催化的不对称电还原偶联已成为有机合成的强有力工具,但是这类反应通常需要牺牲试剂或者牺牲阳极来获得电中性。同时利用阳极和阴极作为工作电极可以很好地解决该问题,然而也面临着诸多挑战:(1)完美匹配阳极氧化和阴极还原反应的电位和速率:(2)精确控制金属氧化态和对映选择性:(3)底物与底物/产物之间的副反应将降低该反应的效率:本文作者开发了一种平行成对电解(PPE)促进的不对称催化新模式,在未分隔的电解池中,利用阳极和阴极分别氧化和还原醇和酮,这两个底物最终同时以较高的产率和对映选择性转化为相应的醛和手性叔醇,除此之外,这种镍催化的不对称还原偶联可以很好地匹配(杂)芳烃的阳极氧化C-H键溴化。该方案为有机电化学的不对称合成提供了新思路。

关键词： organic electrochemistry Nickel catalysis Parallel paired electrolysis Asymmetric catalysis

Electrochemical synthesis of selenocyanated imidazo[1,5-a]quinolines under metal catalyst-and chemical oxidant-free conditions

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Chinese Chemical Letters 2020年第6期31卷 1576-1579页

作者： Jinjin Zhang Huiqiao Wang Yaru Chen Haiquan Xie Chenghua Ding Jiajing Tan Kun Xu College of Chemistry and Pharmaceutical Engineering Nanyang Normal UniversityNanyang 473061China Department of organic Chemistry Faculty of ChemistryBeijing University of Chemical TechnologyBeijing 100029China

Reported herein is the first example of electrochemical selenocyanation of imidazo[1,5-a]quinolines with KSeCN under metal catalyst-and chemical oxidant-free conditions.This sustainable strategy shows a broad scope and great compatibility with functional groups,and affords synthetically and biologically important selenocyanated imidazo[1,5-a]quinolines in good to excellent yields with cheap graphite and Ni plates as the electrodes.The gram-scale synthesis was also successfully conducted,which might demonstrate the potential value of this electrochemical protocol.

关键词： Electrosynthesis organic electrochemistry Anodic oxidation Imidazo[1,5-a]quinoline Selenocyanation

Recent Advances in organic Electrochemical C-H Functionalization

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Chinese Journal of Chemistry 2018年第4期36卷 338-352页

作者： qi-Liang Yang Ping Fan Tian-Sheng Mei State Key Laboratory of Organometallic Chemistry Center for Excellence in Molecular Synthesis Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 China Key Laboratory for Advanced Materials and Institute of Fine Chemicals School of Chemistry & Molecular Engineering East China University of Science and Technology 130 Meilong Road Shanghai 200237 China

organic electrochemistry has a rich history in organic synthesis and has been considered as a promising alternative to traditional chemical oxidants and reductants because it obviates the use of stoichiometric amount of dangerous and toxic reagents. In particular, the electrochemical C-H bonds functionalization is one of the most desirable approaches for the construction of carbon-carbon （C-C） and carbon-heteroatom （C-X） bonds. This review summarizes the substantial progress made in the last few years in C-H functionalization via organic electrochemistry. It is divided into sections on C-C, C-N, C-O, C-S, C-Halogen and C-P bond formation.

关键词： organic electrochemistry C-H functionalization carbon-carbon bond formation carbon-heteroatom bond formation