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A review of enantioselective dual transition metal/photoredox catalysis

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Science China Chemistry 2020年第5期63卷 637-647页

作者： Hong-Hao Zhang Hui Chen chengjian zhu Shouyun Yu Jiangsu Key Laboratory of Advanced Organic Materials School of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023China

Transition metal catalysis is one of the most important tools to construct carbon-carbon and carbon-heteroatom bonds in modern organic synthesis. Visible-light photoredox catalysis has recently drawn considerable attention of the scientific community owing to its unique activation modes and significance for the green synthesis. The merger of photoredox catalysis with transition metal catalysts, termed metallaphotoredox catalysis, has become a popular strategy for expanding the synthetic utility of visiblelight photocatalysis. This strategy has led to the discovery of novel asymmetric transformations, which are unfeasible or not easily accessible by a single catalytic system. This contemporary area of organic chemistry holds promise for the development of economical and environmentally friendly methods for the asymmetric synthesis of chiral compounds. In this review, the advances in the enantioselective metallaphotoredox catalysis(EMPC) are summarized.

关键词： transition metal catalysis photoredox catalysis dual catalysis asymmetric catalysis

Tandem dual C(sp^3)-H/C(sp^2)-H functionalization: a radical cyclization of 2-isocyanobiphenyl with ether to 6-alkylated phenanthridine

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Science China Chemistry 2014年第8期57卷 1172-1175页

作者： PAN ChangDuo HAN Jie zhu chengjian State Key Laboratory of Coordination Chemistry School of Chemistry and Chemical Engineering Nanjing University State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences

A simple and efficient radical coupling of 2-isocyanobiphenyl with ethers was developed, providing a variety of 6-alkylated phenanthridines. Both cyclic and acyclic ethers are suitable substrates for this transformation, which comprised the functional- ization of two C-H bonds： the sp3 C-H of ether and sp2 C-H of phenyl group. The kinetic isotope effect （KIE） revealed that the cleavage of sp3 C-H bond would be involved in the rate-determining step.

关键词： C-H functionalization domino reaction phenanthridine 2-isocyanobiphenyl ether

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Gold-Catalyzed Direct Indolation of Tetrahydroisoquinolines

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Chinese Journal of Chemistry 2012年第12期30卷 2741-2746页

作者： Zhang Yan Luo Sha Feng Bainian zhu chengjian School of Medicine and Pharmaceutics Jiangnan University Wuxi diangsu 214122 China State Key Laboratry of Coordination Chemistrry School of Chemistry and Chemical Engieering Nanjing University Nanjing Jiangsu 210093 China

Nitrogen-containing heterocyclic compounds are important motifs of pharmaceuticals and functional materials, and there has been a growing interest in new synthetic methods for their preparations. In this paper, we report a direct cross-coupling reaction of indole with N-aryl tetrahydroisoquinolines in the presence of gold catalyst. The reaction is compatible with a wide range of substituted indoles, to enable the tbrmation of various alkylated heteroarenest, nder very mild reaction conditions.

关键词： C-H activation sp3 bonds indolation gold heterocyclic compounds

Manganese-Catalyzed Anti-Markovnikov Hydroarylation of Enamides:Modular Synthesis of Arylethylamines

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Chinese Journal of Chemistry 2022年第13期40卷 1546-1552页

作者： Yjie He Chaoyu Du Jian Han Jie Han chengjian zhu Jin Xie State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic Materials Chemistry and Biomedicine Innovation Center(ChemBIC)School of Chemistry and Chemical EngineeringNanjing UniversityNanjingJiangsu 210023China Green Catalysis Center College of Chemistry and Molecular EngineeringZhengzhou UniversityZhengzhouHenan 45000iChina Advanced Catalytic Engineering Research Center of the Ministry of Education Hunan UniversityChangshaHunan 410082China

The arylethylamine framework is a prevalent motif in a great range of biologically important organic *** intractable task for frontline drug discovery is to find structurally new medicine candidates instead of opioid,based on the construction of a rich chemical space of arylethylamine motif In this report,a practical protocol for the synthesis of arylethylamine functionality common in pharmaceutical chemicals has been *** proceeds by Mn-catalyzed anti-Markovnikov hydroarylation of electron-rich enamides under mild conditions without the use of *** spite of mismatched electronic effects during the manganese-mediated migratory insertion process,both terminal and internal enamides can be regioselectively hydroarylated with various aryl boronic acids in 15 ***,the successful hydroalkenylation of enamides with alkenyl boronic acids in air atmosphere affords an elegant route to synthetically useful β-alkenylated amines in satisfactory *** synthetic robustness and practicality of the reaction reveal its simple operation,short reaction time,viability on a gram-scale and its value in late-stage modification of complex molecules.

关键词： Alkenes Anti-Markovnikov Homogeneous catalysis Amines Difunctionalization

Decarboxylative Amination with Nitroarenes via Synergistic Catalysis

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Chinese Journal of Chemistry 2024年第4期42卷 351-355页

作者： Meiling Ding Sitian Zhou Shunruo Yao chengjian zhu Weipeng Li Jin Xie State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic MaterialsChemistry and Biomedicine Innovation Center(ChemBIC)School of Chemistry and Chemical EngineeringNanjing UniversityNanjingJiangsu210023 China Green Catalysis Center and College of ChemistryZhengzhou UniversityZhengzhouHenan450001 China

In this paper,we have developed a decarboxylative amination of carboxylic acids with nitroarenes for the synthesis of secondary *** protocol is performed at mild conditions without the use of noble metals as catalysts.A wide range of structurally diverse secondary amines could be obtained in good yields(up to 94%)with good functional group *** transformation shows good to excellent selectivity,avoiding the generation of over alkylated byproducts.

关键词： Nitroarenes Amines Synergistic catalysis Carboxylic acids Radical alkylation Amination Photocatalysis Steric hindrance

Relay C(sp^(3))-H bond trifluoromethylthiolation and amidation by visible light photoredox catalysis

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Science China Chemistry 2024年第11期67卷 3844-3850页

作者： Junheng Liu Suqi Yang Shunruo Yao chengjian zhu Yong Liu Weipeng Li Jin Xie State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic MaterialsChemistry and Biomedicine Innovation Center(ChemBIC)School of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023China Green Catalysis Center College of ChemistryZhengzhou UniversityZhengzhou 450001China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryShanghai 200032China Nanjing Bready Advanced Materials Technology Co. Ltd.Nanjing 221100China State Key Laboratory of Natural Medicines China Pharmaceutical UniversityNanjing 211198China

Selective functionalization of C(sp^(3))–H bonds is a straightforward and practical method to construct complex molecule skeletons. In this field, direct transformation of unactivated C(sp^(3))–H bonds into C(sp^(3))–SCF_(3) architectures is still a great *** report a highly selective trifluoromethylthiolation of unactivated aliphatic C(sp^(3))–H bonds by combination of proton-coupled electron transfer(PCET) and hydrogen atom transfer(HAT) strategy. A wide range of structurally diverse alkyl trifluoromethyl sulfides are obtained. Furthermore, the use of two different photocatalysts can realize an unprecedented trifluoromethylthiolation and amidation cascade of different C(sp^(3))–H bonds. It can afford a good access to bifunctionalized molecules in synthetically useful yields.

关键词： photoredox catalysis C–H activation trifluoromethylthiolation amidation PCET

Dinuclear gold-catalyzed C–H bond functionalization of cyclopropenes

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Science China Chemistry 2021年第11期64卷 1958-1963页

作者： Kai Liu Tingrui Li Duan-Yang Liu Weipeng Li Jian Han chengjian zhu Jin Xie State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic MaterialsChemistry and Biomedicine Innovation Center(ChemBIC)School of Chemistry and Chemical EngineeringNanjing UniversityNanjing210023China College of Chemical Engineering Zhejiang University of TechnologyHangzhou310014China College of Chemistry and Molecular Engineering Zhengzhou UniversityZhengzhou450001China Advanced Catalytic Engineering Research Center of the Ministry of Education Hunan UniversityChangsha410082China

We report an unprecedented C-H bond functionalization of cyclopropenes enabled by dinuclear gold *** selective C-H allylation,alkynylation and halogenation of cyclopropenes with organic halides have been *** reaction does not require strong external oxidants and affords access to functionalized cyclopropenes in moderate to good *** reductive elimination process to controllably construct C-C or C-X bonds can be tuned by using different dinuclear gold catalysts.

关键词： cyclopropenes gold catalysis allylation alkynylation C–H activation

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Decarboxylative Acylation of Carboxylic Acids:Reaction Investigation and Mechanistic Study

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CCS Chemistry 2022年第7期4卷 2469-2480页

作者： Xiaopeng Wu Jie Han Siyu Xia Weipeng Li chengjian zhu Jin Xie State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic MaterialsChemistry and Biomedicine Innovation Center(ChemBIC)School of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023 State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryShanghai 200032 Advanced Catalytic Engineering Research Center of the Ministry of Education Hunan UniversityChangsha 410082

Ketones serve as one of the most critical building blocks in organic synthesis,involving numerous functional group ***,we rep ort an unprecedented photoredox-nickel metallap hotoredox-catalyzed decarboxylative acylation of common aliphatic acids with readily available aromatic and aliphatic thioesters.A wide range of structurally diverse asymmetrical aryl alkyl and dialkyl ketones have been constructed in yields of up to 98% with this *** protocol has excellent reaction selectivity and functional group compatibility,representing a significant step forward in ketone *** one-pot decarboxylative acylation at the gram scale from two different carboxylic acids and the late-stage application for the synthesis of complex ketones shows its synthetic *** mechanistic experiments and density functional theory(DFT)calculations suggest that the decarboxylative acylation reaction operates via an underdeveloped Ni(Ⅰ)-Ni(Ⅱ)-Ni(Ⅰ)-Ni(Ⅲ)-Ni(Ⅰ)catalytic cycle.

关键词： metallaphotoredox decarboxylative acylation ketones synthesis dual-catalysis carboxylic acid

Photoredox Catalyzed Inert Bond Functionalization

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Photoredox Catalyzed Inert Bond Functionalization