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学者姓名:叶克印
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Abstract :
We present here a catalytic enantioconvergent amination of alcohols for efficient access to chiral C2- and C3-substituted benzomorpholines. The racemic amino alcohol substrates of different substitution patterns, which are readily available from a common precursor, can be converted to the enantioenriched heterocycles in a highly atom- and step-economical fashion. In particular, an unprecedented asymmetric amination of racemic primary alcohols via dynamic kinetic resolution is achieved under cooperative iridium/iron catalysis, resulting in highly enantioendifficult to access otherwise. [GRAPHICS] .
Keyword :
atom economy atom economy divergent synthesis divergent synthesis dynamic kinetic resolution dynamic kinetic resolution enantioconvergent heterocycle synthesis enantioconvergent heterocycle synthesis redox-neutral catalysis redox-neutral catalysis substituted benzomorpholines substituted benzomorpholines
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GB/T 7714 | Gao, Yaru , Hong, Guorong , Zhang, Lei et al. Asymmetric Amination of Primary Alcohols via Dynamic Kinetic Resolution: Enantioconvergent Access to Chiral Benzomorpholines [J]. | CCS CHEMISTRY , 2025 , 7 (1) : 80-90 . |
MLA | Gao, Yaru et al. "Asymmetric Amination of Primary Alcohols via Dynamic Kinetic Resolution: Enantioconvergent Access to Chiral Benzomorpholines" . | CCS CHEMISTRY 7 . 1 (2025) : 80-90 . |
APA | Gao, Yaru , Hong, Guorong , Zhang, Lei , Ye, Ke-Yin , Cheng, Jiajia , Yang, Bin-Miao et al. Asymmetric Amination of Primary Alcohols via Dynamic Kinetic Resolution: Enantioconvergent Access to Chiral Benzomorpholines . | CCS CHEMISTRY , 2025 , 7 (1) , 80-90 . |
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In most Suzuki-Miyaura carbon-carbon cross-coupling reactions,the borabicyclo[3.3.1]nonane scaffold(9-BBN)only serves as an auxiliary facilitating the transmetalation step and thus is transformed into by-products.There are rare examples where the 9-BBN derivatives serve as the potentially diverse C8 building blocks in cross-coupling reactions.Herein,we report a cobalt-catalyzed migratory carbon-carbon cross-coupling reaction of the in situ formed 9-BBN ate complexes to afford diverse aryl-and alkyl-functionalized cyclooctenes.Preliminary mechanistic studies suggest the oxidation-induced cis-bicyclo[3.3.0]oct-1-ylborane is the key intermediate in this migratory cross-coupling reaction,which pro-motes the development of other diverse migratory cross-coupling of borate complexes.
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GB/T 7714 | Peng Guo , Shicheng Dong , Xiang-Gui Zhang et al. Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane(9-BBN)borates [J]. | 中国化学快报(英文版) , 2025 , 36 (4) : 139-143 . |
MLA | Peng Guo et al. "Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane(9-BBN)borates" . | 中国化学快报(英文版) 36 . 4 (2025) : 139-143 . |
APA | Peng Guo , Shicheng Dong , Xiang-Gui Zhang , Bing-Bin Yang , Jun Zhu , Ke-Yin Ye . Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane(9-BBN)borates . | 中国化学快报(英文版) , 2025 , 36 (4) , 139-143 . |
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This study presents an efficient method for synthesizing twisted benzo-extended [n]phenacenes ([n]BPs) featuring an electrochemical flow (e-flow) Scholl reaction of the corresponding [n]BP precursors from a one-pot three-component Suzuki-Miyaura coupling reaction. The e-flow Scholl reaction offers advantages such as reduced oxidant usage and overoxidation byproducts, and easy scale-up through extended electrolysis time toward these intricate polycyclic aromatic hydrocarbons. In addition, the increase in molecular length decreases the optical bandgap of [n]BPs and thus tunes their photophysical properties. This work provides a green and sustainable synthetic strategy for diverse [n]BPs and enables facile bandgap modulation through pi-conjugation extension, offering potential for organic semiconductor applications in optoelectronic devices.
Keyword :
Continuous flow Continuous flow electrosynthesis electrosynthesis GNRs GNRs phenacene phenacene Scholl reaction Scholl reaction
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GB/T 7714 | Wang, Qiang , Wang, Wei-Zhen , Zhang, Ruiying et al. Benzo-Extended [n]Phenacenes: e-Flow Synthesis and Length-Dependent Properties [J]. | JACS AU , 2025 , 5 (9) : 4281-4287 . |
MLA | Wang, Qiang et al. "Benzo-Extended [n]Phenacenes: e-Flow Synthesis and Length-Dependent Properties" . | JACS AU 5 . 9 (2025) : 4281-4287 . |
APA | Wang, Qiang , Wang, Wei-Zhen , Zhang, Ruiying , Zhai, Zi'ang , Chen, Xinyu , Li, Minggang et al. Benzo-Extended [n]Phenacenes: e-Flow Synthesis and Length-Dependent Properties . | JACS AU , 2025 , 5 (9) , 4281-4287 . |
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有机电化学被国际纯粹与应用化学联合会(IUPAC)列入2023年度化学领域十大新兴技术之一.作为基础化学的重要分支,电化学在本科阶段主要是在无机化学中的"氧化还原反应"和物理化学中的"电解质溶液"等章节介绍了电化学基础知识,但对有机电化学的知识却鲜有提及.本文主要介绍近年来有机电化学的研究热点,并探讨在本科教学中引入有机电化学相关知识的几点思考.
Keyword :
有机电化学 有机电化学 本科教学 本科教学 氧化还原反应 氧化还原反应 电化学合成 电化学合成
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GB/T 7714 | 晏宏 , 王文峰 , 叶克印 et al. 有机电化学与化学教学 [J]. | 大学化学 , 2025 , 40 (5) : 301-310 . |
MLA | 晏宏 et al. "有机电化学与化学教学" . | 大学化学 40 . 5 (2025) : 301-310 . |
APA | 晏宏 , 王文峰 , 叶克印 , 袁耀锋 . 有机电化学与化学教学 . | 大学化学 , 2025 , 40 (5) , 301-310 . |
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Vicinal diamines are an important structural motif that has been widely used in biological, medicinal, and materials science. Transition-metal-catalyzed diazidation of alkene is a straightforward and efficient approach for vicinal diamines, which are unfavorably associated with excess oxidants and limited substrate scope for electron-deficient alkenes. Herein we report an electrocatalytic diazidation of alkenes with the electrode coated by Cu nanoparticles pyrolyzed from Cu(salen)-based metal-organic framework. This strategy is compatible with various alkenes including those electro-deficient ones. Remarkably, the modified electrode maintains high electrocatalytic activity for diazidation even after 15 cycles.
Keyword :
Alkenes Alkenes Copper nanoparticles Copper nanoparticles Diazidation Diazidation Electrocatalysis Electrocatalysis Metal-organic frameworks Metal-organic frameworks
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GB/T 7714 | He, Xinglei , Zhu, Xiaobin , Wang, Luyao et al. Electrocatalytic diazidation of alkenes with modified electrodes coated by Cu nanoparticles [J]. | TETRAHEDRON , 2025 , 176 . |
MLA | He, Xinglei et al. "Electrocatalytic diazidation of alkenes with modified electrodes coated by Cu nanoparticles" . | TETRAHEDRON 176 (2025) . |
APA | He, Xinglei , Zhu, Xiaobin , Wang, Luyao , Li, Jingheng , Yu, Chunlong , Ye, Ke-Yin . Electrocatalytic diazidation of alkenes with modified electrodes coated by Cu nanoparticles . | TETRAHEDRON , 2025 , 176 . |
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Sulfonimidoyl fluorides, the chiral aza-isosteres of sulfonyl fluorides, have gained increasing attention as a powerful linkage agent in the sulfur(VI)-fluoride exchange reaction (SuFEx). The hexavalent sulfonimidoyl fluorides are typically prepared from organosulfur in high oxidation states. We report herein an electrochemical approach using the readily available, bench-stable, yet underexplored tetravalent sulfinamidines without external chemical oxidants. The usefulness of the obtained sulfonimidoyl fluorides is demonstrated by their versatile SuFEx reactivity.
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GB/T 7714 | Zeng, Ding-Bo , Zhao, Bin , Gong, Chen-Xu et al. Electrochemical Conversions of Sulfinamidines into Sulfonimidoyl Fluorides [J]. | ORGANIC LETTERS , 2025 . |
MLA | Zeng, Ding-Bo et al. "Electrochemical Conversions of Sulfinamidines into Sulfonimidoyl Fluorides" . | ORGANIC LETTERS (2025) . |
APA | Zeng, Ding-Bo , Zhao, Bin , Gong, Chen-Xu , Lin, Yuqi , Ye, Ke-Yin . Electrochemical Conversions of Sulfinamidines into Sulfonimidoyl Fluorides . | ORGANIC LETTERS , 2025 . |
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Alternating current electrolysis has emerged as a promising technique for addressing challenging redox reactions that are otherwise difficult or impossible for direct current electrolysis. Under mild and transition-metal-free reaction conditions, a general electrochemical denitrative cyclization of nitroarenes was developed to access various cyclic sulfone-containing derivatives of biological significance. The key to success lies in the facile manipulation of multiple redox events upon rapid alternating polarity switching to enhance the selectivity and efficiency.
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GB/T 7714 | Zhu, Shuang-Jun , Lin, Yi-Chao , Yuan, Guo-Cai et al. Electrochemical Denitrative Cyclization Driven by Alternating Polarity [J]. | ORGANIC LETTERS , 2025 , 27 (5) : 1186-1191 . |
MLA | Zhu, Shuang-Jun et al. "Electrochemical Denitrative Cyclization Driven by Alternating Polarity" . | ORGANIC LETTERS 27 . 5 (2025) : 1186-1191 . |
APA | Zhu, Shuang-Jun , Lin, Yi-Chao , Yuan, Guo-Cai , He, Xinglei , Yu, Chunlong , Ye, Ke-Yin . Electrochemical Denitrative Cyclization Driven by Alternating Polarity . | ORGANIC LETTERS , 2025 , 27 (5) , 1186-1191 . |
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In most Suzuki-Miyaura carbon-carbon cross-coupling reactions, the borabicyclo[3.3.1]nonane scaffold (9-BBN) only serves as an auxiliary facilitating the transmetalation step and thus is transformed into by-products. There are rare examples where the 9-BBN derivatives serve as the potentially diverse C8 building blocks in cross-coupling reactions. Herein, we report a cobalt-catalyzed migratory carbon- carbon cross-coupling reaction of the in situ formed 9-BBN ate complexes to afford diverse aryl- and alkyl-functionalized cyclooctenes. Preliminary mechanistic studies suggest the oxidation-induced cis- bicyclo[3.3.0]oct-1-ylborane is the key intermediate in this migratory cross-coupling reaction, which promotes the development of other diverse migratory cross-coupling of borate complexes. (c) 2025 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
Keyword :
Borate Borate Cobalt Cobalt Cross-coupling Cross-coupling Cyclooctene Cyclooctene Rearrangement Rearrangement
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GB/T 7714 | Guo, Peng , Dong, Shicheng , Zhang, Xiang-Gui et al. Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane (9-BBN) borates [J]. | CHINESE CHEMICAL LETTERS , 2025 , 36 (4) . |
MLA | Guo, Peng et al. "Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane (9-BBN) borates" . | CHINESE CHEMICAL LETTERS 36 . 4 (2025) . |
APA | Guo, Peng , Dong, Shicheng , Zhang, Xiang-Gui , Yang, Bing-Bin , Zhu, Jun , Ye, Ke-Yin . Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane (9-BBN) borates . | CHINESE CHEMICAL LETTERS , 2025 , 36 (4) . |
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In contrast to the well-established synthetic protocols for monoalkenyl halides, a general approach to access diverse distal bisalkenyl halides with high synthetic fidelity has not yet been established, which are found in various biologically active natural products and may also serve as useful building blocks in organic synthesis. We herein report a cobalt-catalyzed regioand stereoselective deoxygenative hydrohalogenation of propargyl alcohols to access Z-configurated alkenyl halides and the analogous distal bisalkenyl chlorides, bromides, and iodides. Mechanistic investigation suggests that the regioand stereoselective stepwise hydrogenation of in situ generated chloroallenes is the key step wherein the commercially available halodimethylsilane, or a surrogate combination of hydrosilane and halosilane, serves both as the hydrogen and chlorine sources. (c) 2025 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
Keyword :
Cobalt catalysis Cobalt catalysis Halosilane Halosilane Organohalides Organohalides Propargyl alcohols Propargyl alcohols Regioselectivity Regioselectivity
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GB/T 7714 | Wang, Zhihua , Zhu, Xiang-Zhao , He, Xinglei et al. Deoxygenative hydrohalogenation of propargyl alcohols: Regio- and stereoselective synthesis of unsaturated distal dihalides [J]. | CHINESE CHEMICAL LETTERS , 2025 , 36 (12) . |
MLA | Wang, Zhihua et al. "Deoxygenative hydrohalogenation of propargyl alcohols: Regio- and stereoselective synthesis of unsaturated distal dihalides" . | CHINESE CHEMICAL LETTERS 36 . 12 (2025) . |
APA | Wang, Zhihua , Zhu, Xiang-Zhao , He, Xinglei , Gong, Chen-Xu , Liang, Wang-Fu , Wang, Wenfeng et al. Deoxygenative hydrohalogenation of propargyl alcohols: Regio- and stereoselective synthesis of unsaturated distal dihalides . | CHINESE CHEMICAL LETTERS , 2025 , 36 (12) . |
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Chiral sulfinamides find broad applications in bioactive compounds, chiral auxiliaries, chiral ligands, and organocatalysts. However, biocatalytic approaches for their enantioselective synthesis have rarely been explored. Herein, an efficient biocatalytic strategy for the synthesis of chiral sulfinamides via polycyclic ketone monooxygenase (PockeMO) catalyzed asymmetric oxidation of sulfenamides was reported. A diverse array of chiral sulfinamides can be readily accessed with high yields (up to >99%) and enantioselectivities (>99:1 er). Additionally, this biocatalytic platform was scalable, and the resulting synthetic chiral sulfinamides could be easily derivatized to various chiral S-stereogenic compounds. Molecular dynamics simulation studies revealed that hydrogen bonding interactions between the sulfenamides and key residues were essential for enantioselectivity control. This work unlocks a biocatalytic avenue to access chiral sulfinamides for synthetic chemistry and drug discovery.
Keyword :
asymmetric oxidation asymmetric oxidation biocatalysis biocatalysis chiralsulfinamides chiralsulfinamides polycyclic ketone monooxygenase (PockeMO) polycyclic ketone monooxygenase (PockeMO) sulfenamides sulfenamides
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GB/T 7714 | Xue, Wanqing , Lin, Yuqi , Lin, Xiaomin et al. Synthesis of Chiral Sulfinamides Enabled by Polycyclic Ketone Monooxygenase Catalyzed Asymmetric Oxidation of Sulfenamides [J]. | ACS CATALYSIS , 2025 , 15 (18) : 16247-16253 . |
MLA | Xue, Wanqing et al. "Synthesis of Chiral Sulfinamides Enabled by Polycyclic Ketone Monooxygenase Catalyzed Asymmetric Oxidation of Sulfenamides" . | ACS CATALYSIS 15 . 18 (2025) : 16247-16253 . |
APA | Xue, Wanqing , Lin, Yuqi , Lin, Xiaomin , Xu, Xinqi , Chen, Jingjing , Lin, Juan et al. Synthesis of Chiral Sulfinamides Enabled by Polycyclic Ketone Monooxygenase Catalyzed Asymmetric Oxidation of Sulfenamides . | ACS CATALYSIS , 2025 , 15 (18) , 16247-16253 . |
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