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学者姓名：宋秋玲
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Abstract ：
A practical method for the construction of difluoromethylene-containing 1,4-thiazine moieties using readily available diethyl bromodifluoromethanephosphonate (BrCF2 PO(OEt)2 ) as difluorocarbene precusor has been developed. This transformation features the efficient capture of difluorocarbene by pyridinium 1,4zwitterionic thiolates. A series of structurally novel and functionalized difluoromethylene-containing 1,4thiazine derivatives were thus synthesized in good yields. (c) 2024 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
Keyword ：
4-Thiazine derivatives 4-Thiazine derivatives 4-zwitterionic thiolates 4-zwitterionic thiolates Difluoromethylene Difluoromethylene Pyridinium 1 Pyridinium 1
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| GB/T 7714 | Chen, Zhiwei , Sheng, Heyun , Li, Xue et al. Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives [J]. | CHINESE CHEMICAL LETTERS , 2024 , 35 (4) . |
| MLA | Chen, Zhiwei et al. "Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives" . | CHINESE CHEMICAL LETTERS 35 . 4 (2024) . |
| APA | Chen, Zhiwei , Sheng, Heyun , Li, Xue , Chen, Menghan , Li, Xin , Song, Qiuling . Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives . | CHINESE CHEMICAL LETTERS , 2024 , 35 (4) . |
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Abstract ：
立体化学纯的肟被广泛应用于有机合成、药物、食品添加剂等领域。传统方法合成肟的立体选择性取决于底物取代基的空间位阻，其立体选择性合成一直是有机合成领域的难点与挑战。本文简要介绍了立体选择性合成肟的新方法和技术的研究进展。本文的内容来源于基础有机化学，将此内容融入到教学中可以拓展学生的视野，也有助于激发学生发现和解决难题的兴趣。
Keyword ：
交叉偶联 交叉偶联 光异构化 光异构化 立体选择性 立体选择性 肟 肟 贝克曼重排 贝克曼重排
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| GB/T 7714 | 张圳 , 杨凯 , 宋秋玲 . 肟的立体选择性合成概述 [J]. | 大学化学 , 2024 , 39 (01) : 105-110 . |
| MLA | 张圳 et al. "肟的立体选择性合成概述" . | 大学化学 39 . 01 (2024) : 105-110 . |
| APA | 张圳 , 杨凯 , 宋秋玲 . 肟的立体选择性合成概述 . | 大学化学 , 2024 , 39 (01) , 105-110 . |
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Chiral phosphorus-containing compounds find applications across various fields, including asymmetric catalysis, medicinal chemistry, and materials science. Despite the abundance of reported highly enantioselective methods for synthesizing various chiral phosphorus compounds, the enantioselective synthesis of alpha-boryl phosphorus compounds still remains an unknown territory. Here, we report a method for the construction of chiral alpha-boryl phosphates by asymmetric B-H insertion reaction using alpha-diazo phosphates as carbene precursors, cheap and readily available copper salt as the catalyst and chiral oxazoline as the ligand. This method can directly afford a series of stable alpha-boryl phosphates with a yield up to 97% and an enantioselectivity up to 98% ee. The operating procedure of this method is straightforward, offering a broad substrate applicability, remarkable tolerance towards various functional groups, and gentle reaction conditions. Chiral phosphorus-containing compounds find applications across various fields, including asymmetric catalysis, medicinal chemistry, and materials science.
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| GB/T 7714 | Li, Longlong , Yu, Kui , An, Hejun et al. Enantioselective copper-catalyzed B-H bond insertion reaction of α-diazo phosphonates to access chiral α-boryl phosphonates [J]. | CHEMICAL SCIENCE , 2024 , 15 (19) : 7130-7135 . |
| MLA | Li, Longlong et al. "Enantioselective copper-catalyzed B-H bond insertion reaction of α-diazo phosphonates to access chiral α-boryl phosphonates" . | CHEMICAL SCIENCE 15 . 19 (2024) : 7130-7135 . |
| APA | Li, Longlong , Yu, Kui , An, Hejun , Cai, Xinping , Song, Qiuling . Enantioselective copper-catalyzed B-H bond insertion reaction of α-diazo phosphonates to access chiral α-boryl phosphonates . | CHEMICAL SCIENCE , 2024 , 15 (19) , 7130-7135 . |
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Compared with well-developed radical aromatic ring migration, heteroatomic radical migration and alkenyl radical migration remain challenging. Herein, a photoinduced remote radical migration reaction based on the aromatic skeleton through tetracoordinate boron species has been developed. In this work, commercially available diboron reagent (B2pin2) or alkenyl boron (alkenylBpin) react with o-bromostyr- enes as well as their analogues under the mediation of lithium reagents in a single-vessel reaction. This process undergoes an interesting 1,4-, 1,5- or 1,6remote radical migration via intramolecular circular transition state, which introduces a large array of boron-migrative or alkenyl-migrative compounds. In particular, the 1,6-radical migration reaction has not been reported before. This protocol features readily accessible starting materials, high atom economy, broad substrate scope and diversified valuable products with Csp3-B and Csp2-B bonds obtained simultaneously with B2pin2 or portrays alkenyl-migrative module and excellent E/Z selectivity with alkenylBpins.
Keyword ：
alkenyl radical migration alkenyl radical migration boryl radical migration boryl radical migration lithium reagent lithium reagent remote migration remote migration tetracoordinate boron species tetracoordinate boron species
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| GB/T 7714 | Li, Chaokun , Chen, Nan , Yao, Tangfeng et al. Remote Boryl and Alkenyl Radical Migration of Olefin-Bearing Aryl Bromides [J]. | CCS CHEMISTRY , 2024 . |
| MLA | Li, Chaokun et al. "Remote Boryl and Alkenyl Radical Migration of Olefin-Bearing Aryl Bromides" . | CCS CHEMISTRY (2024) . |
| APA | Li, Chaokun , Chen, Nan , Yao, Tangfeng , Zhao, Chenchen , Liao, Shangteng , Song, Qiuling . Remote Boryl and Alkenyl Radical Migration of Olefin-Bearing Aryl Bromides . | CCS CHEMISTRY , 2024 . |
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Organoboron compounds are environmentally benign, have low toxicity and are versatile reagents that are extensively employed in organic synthesis, especially in the realm of asymmetric synthesis. The last several decades have witnessed a tremendous outburst of asymmetric reactions based on various organoboron compounds. Among them, 1,1-diborylalkanes, which contain two boryl groups at the same sp3-carbon atom, are regarded as some of the most versatile and powerful reagents for their unique structure and unusual reaction mode in organic synthesis. Moreover, owing to the stabilizing effect of the empty p-orbital of the neighboring boron atoms and the inherent good steric-hindrance, 1,1-diborylalkanes often exhibit extraordinary reactivity and stereoselectivity compared to other kinds of organoboron compounds in asymmetric synthesis. Herein, the present highlight summarizes and discusses the recent progress achieved in the catalytic enantioselective reactions of 1,1-diborylalkanes during the past decade. Structurally unique 1,1-diborylalkanes often exhibit unusual reactivity and excellent stereoselectivity in asymmetric synthesis. This highlight summarizes and discusses recent advances in the catalytic enantioselective reactions of these reagents.
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| GB/T 7714 | Li, Xin , Chen, Jinglong , Song, Qiuling . Recent progress in the catalytic enantioselective reactions of 1,1-diborylalkanes [J]. | CHEMICAL COMMUNICATIONS , 2024 , 60 (18) : 2462-2471 . |
| MLA | Li, Xin et al. "Recent progress in the catalytic enantioselective reactions of 1,1-diborylalkanes" . | CHEMICAL COMMUNICATIONS 60 . 18 (2024) : 2462-2471 . |
| APA | Li, Xin , Chen, Jinglong , Song, Qiuling . Recent progress in the catalytic enantioselective reactions of 1,1-diborylalkanes . | CHEMICAL COMMUNICATIONS , 2024 , 60 (18) , 2462-2471 . |
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1,2-Difunctionalization of alkynes offers a straightforward approach to access polysubstituted alkenes. However, simultaneous multi-component cascade transformations including difunctionalization of two alkynes with both syn- and anti-selectivity in one catalyst system is undeveloped and proves to be a significant challenge. Herein, we report a Nickel-catalyzed four-component reaction to access polysubstituted 1,3-dienes using two terminal alkynes, aryl boroxines, and perfluoroalkyl iodides, wherein the reaction forms three new C-C bonds in a single vessel and serve as a modular strategy to access polysubstituted 1,3-dienes with excellent chemoselectivity, good regioselectivity and exclusive stereoselectivity. Control experiments reveal the plausible reaction mechanism and DFT calculations explain the cause for the formation of this unusual four-component reaction. Furthermore, we successfully incorporate two biologically active units into 1,2,3,4-tetrasubstituted 1,3-dienes, which greatly increases the diversity of molecular scaffolds and brings more potential values to medicinal chemistry, the synthetic utility of our protocol is further demonstrated by the late-stage transformations. © The Author(s) 2024.
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| GB/T 7714 | Chen, S. , Wang, Y.-N. , Xie, J. et al. Chemo-, regio- and stereoselective access to polysubstituted 1,3-dienes via Nickel-catalyzed four-component reactions [J]. | Nature Communications , 2024 , 15 (1) . |
| MLA | Chen, S. et al. "Chemo-, regio- and stereoselective access to polysubstituted 1,3-dienes via Nickel-catalyzed four-component reactions" . | Nature Communications 15 . 1 (2024) . |
| APA | Chen, S. , Wang, Y.-N. , Xie, J. , Li, W. , Ye, M. , Ma, X. et al. Chemo-, regio- and stereoselective access to polysubstituted 1,3-dienes via Nickel-catalyzed four-component reactions . | Nature Communications , 2024 , 15 (1) . |
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Skeletal editing of N-heterocycles has recently received considerable attention, and the introduction of boron atom into heterocycles often results in positive property changes. However, direct enlargement of N-heterocycles through boron atom insertion is rarely reported in the literature. Here, we report a N-heterocyclic editing reaction through the combination boron atom insertion and C-H borylation, accessing the fused-BN-heterocycles. The synthetic potential of this chemistry was demonstrated by substrate scope and late-stage diversification of products.
Keyword ：
Azaborine Azaborine C-H Borylation C-H Borylation N-Heterocycles N-Heterocycles Nickel Nickel Reductive Coupling Reductive Coupling
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| GB/T 7714 | Zhang, Xu , Su, Wanlan , Guo, Huosheng et al. N-Heterocycle-Editing to Access Fused-BN-Heterocycles via Ring-Opening/C-H Borylation/Reductive C-B Bond Formation [J]. | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION , 2024 , 63 (10) . |
| MLA | Zhang, Xu et al. "N-Heterocycle-Editing to Access Fused-BN-Heterocycles via Ring-Opening/C-H Borylation/Reductive C-B Bond Formation" . | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 63 . 10 (2024) . |
| APA | Zhang, Xu , Su, Wanlan , Guo, Huosheng , Fang, Pengyuan , Yang, Kai , Song, Qiuling . N-Heterocycle-Editing to Access Fused-BN-Heterocycles via Ring-Opening/C-H Borylation/Reductive C-B Bond Formation . | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION , 2024 , 63 (10) . |
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The [1,2]- and [2,3]-Stevens rearrangements are one of the most fascinating chemical bond reorganization strategies in organic chemistry, and they have been demonstrated in a wide range of applications, representing a fundamental reaction tactic for the synthesis of nitrogen compounds in chemical community. However, their applicabilities are limited by the scarcity of efficient, general, and straightforward methods for generating ammonium ylides. Herein, we report a general difluorocarbene-induced tertiary amine-involved [1,2]- and [2,3]-Stevens rearrangements stemmed from in situ generated difluoromethyl ammonium ylides, which allows for the rearrangements of versatile tertiary amines bearing either allyl, benzyl, or propargyl groups, resulting in the corresponding products in one reaction under the same reaction conditions with a general way. Broad substrate scope, simple operation, mild reaction conditions and late-stage modification of natural products highlight the advantages of this strategy, meanwhile, this general rearrangement reaction is believed to bring opportunities for the transformations of nitrogen ylides and the assembly of valuable tertiary amines and amino acids. This will further enrich the reaction repertoire of difluorocarbene species, facilitate the development of reactions involving difluoromethyl ammonium salts, and provide an avenue for the development of this type of rearrangement reactions. © The Author(s) 2024.
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| GB/T 7714 | Su, J. , Guo, Y. , Li, C. et al. Difluorocarbene-induced [1,2]- and [2,3]-Stevens rearrangement of tertiary amines [J]. | Nature Communications , 2024 , 15 (1) . |
| MLA | Su, J. et al. "Difluorocarbene-induced [1,2]- and [2,3]-Stevens rearrangement of tertiary amines" . | Nature Communications 15 . 1 (2024) . |
| APA | Su, J. , Guo, Y. , Li, C. , Song, Q. . Difluorocarbene-induced [1,2]- and [2,3]-Stevens rearrangement of tertiary amines . | Nature Communications , 2024 , 15 (1) . |
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Catalytic enantioselective borylation reactions of unsaturated bonds as powerful tools for the synthesis of diverse chiral organoboron compounds have gained much attention and have wide applications in various fields. However, the atroposelective arylboration reaction with carbon-carbon triple bonds of 1,3-enynes to obtain axially chiral 1,3-dienylboronates remains an elusive and significant challenge. Hence, we develop a cooperative copper- and palladium-catalyzed arylboration reaction to assemble plentiful function enriched axially chiral 1,3-dienylboronates in a single step from easily available 1,3-enynes, B2pin2, and aryl bromides with high levels of chemo-, regio-, stereo-, and atroposelectivity. The mild reaction conditions lead to good functional group tolerance, which is proven by the broad substrate scope and late-stage functionalizations of bioactive compounds or drug molecules. Moreover, the reaction can be easily scaled up, and a series of further transformations can be achieved. It is worth emphasizing that several olefin catalysts and ligands with axial chirality can also be synthesized through the corresponding elaborations of such products, which further explains the powerful transformative ability and application potential of such axially chiral 1,3-dienylboronates. The mechanism experiment and density functional theory (DFT) calculations revealed the cooperative process of copper and palladium catalysis, indicating that the chemoselectivity and regioselectivity of boration are determined by the enyne insertion step on copper, and the atroposelectivity is controlled by the further reductive elimination on the palladium center. Meanwhile, the calculation also demonstrated that the distinct interactions between the P═O and C═O groups with the Pd or Bpin center in the key transition state lead to the formation of products with varying configurations while employing identical configuration ligands. © 2024 American Chemical Society.
Keyword ：
1,3-dienylboronates 1,3-dienylboronates 1,3-enynes 1,3-enynes arylboration arylboration asymmetric catalysis asymmetric catalysis axial chirality axial chirality
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| GB/T 7714 | Li, W. , Chen, H. , Zheng, Y. et al. Copper- and Palladium-Cocatalyzed Chemo-, Regio-, Stereo-, and Atroposelective Arylboration of 1,3-Enynes [J]. | ACS Catalysis , 2024 , 14 (15) : 11318-11331 . |
| MLA | Li, W. et al. "Copper- and Palladium-Cocatalyzed Chemo-, Regio-, Stereo-, and Atroposelective Arylboration of 1,3-Enynes" . | ACS Catalysis 14 . 15 (2024) : 11318-11331 . |
| APA | Li, W. , Chen, H. , Zheng, Y. , Lu, Y. , Xie, J. , Chen, S. et al. Copper- and Palladium-Cocatalyzed Chemo-, Regio-, Stereo-, and Atroposelective Arylboration of 1,3-Enynes . | ACS Catalysis , 2024 , 14 (15) , 11318-11331 . |
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During the past decade, radical difluoromethylation has emerged as a powerful and versatile tool for the incorporation of difluoromethyl into various organic compounds. These reactions feature mild reaction conditions, very good functional group compatibilities, and quite broad substrate scopes, thus having drawn much attention and got rapid developments. A diverse range of difluoromethyl radical precursors have been developed for a series of radical difluoromethylation reactions. This review summarizes and discusses the advance in the radical difluoromethylation reactions, which are organized according to the protocols of generating difluoromethyl radical. During the past decade, radical difluoromethylation has received much attention and rapid developments for its mild reaction conditions and good functional group compatibilities. A diverse array of difluoromethyl radical precursors and corresponding radical reactions have been disclosed. This review summarizes and discusses the recent progress on the radical difluoromethylation reactions, which are organized according to the protocols of generating difluoromethyl radical. image
Keyword ：
difluoromethyl difluoromethyl electrosynthesis electrosynthesis fluorine fluorine photoredox photoredox radical radical
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| GB/T 7714 | Li, Xin , Song, Qiuling . Introduction of Difluoromethyl Through Radical Pathways [J]. | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY , 2024 , 27 (31) . |
| MLA | Li, Xin et al. "Introduction of Difluoromethyl Through Radical Pathways" . | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 27 . 31 (2024) . |
| APA | Li, Xin , Song, Qiuling . Introduction of Difluoromethyl Through Radical Pathways . | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY , 2024 , 27 (31) . |
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