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学者姓名：杨凯
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Abstract ：
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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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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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 . |
| 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 (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 . |
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Bioisosteric replacement has emerged as a clear strategy for drug-structure optimization. Naphthalene is the core element of many chiral pharmaceuticals and drug candidates. However, as a promising isostere of naphthalene, the chiral version of 1,2-benzazaborine has rarely been explored due to the lack of efficient synthetic methods. Here we describe a copper-catalysed enantioselective hydroboration of alkenes with 1,2-benzazaborines. The method provides a general platform for the atom-economic and efficient construction of diverse chiral 1,2-benzazaborine compounds (more than 60 examples) that bear a 2-carbon-stereogenic centre or allene skeleton in high yields and excellent enantioselectivities. Three 1,2-benzazaborine analogues of bioactive chiral naphthalene-containing molecules have been prepared, and a series of transformations around chiral 1,2-benzazaborines have also been developed. Notably, the hydroboration process of this study reveals that the identity of 1,2-benzazaborine plays an essential role in the rate-determining step and catalyst resting state. Chiral 1,2-benzazaborines are promising isosteres of naphthalene, but rarely explored due to the lack of efficient synthetic methods. Now, the copper-catalysed enantioselective hydroboration of alkenes with 1,2-benzazaborines has been developed, providing a general platform for the atom-economic and efficient construction of diverse chiral 1,2-benzazaborine compounds bearing a 2-carbon-stereogenic centre or allene skeleton.
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| GB/T 7714 | Su, Wanlan , Zhu, Jide , Chen, Yu et al. Copper-catalysed asymmetric hydroboration of alkenes with 1,2-benzazaborines to access chiral naphthalene isosteres [J]. | NATURE CHEMISTRY , 2024 . |
| MLA | Su, Wanlan et al. "Copper-catalysed asymmetric hydroboration of alkenes with 1,2-benzazaborines to access chiral naphthalene isosteres" . | NATURE CHEMISTRY (2024) . |
| APA | Su, Wanlan , Zhu, Jide , Chen, Yu , Zhang, Xu , Qiu, Weihua , Yang, Kai et al. Copper-catalysed asymmetric hydroboration of alkenes with 1,2-benzazaborines to access chiral naphthalene isosteres . | NATURE CHEMISTRY , 2024 . |
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Herein we present a practical approach for preparing 10B-enriched 2,1-borazaronaphthalenes from o-aminostyrenes and 10BF3 (the primary source of boron-10) in the presence of chlorosilane. The synthetic potential of this transformation is showcased by the satisfactory substrate scope, scale-up reaction and late-stage modification of 10B-enriched molecules. The preliminary mechanistic studies suggest that this 10B transformation may involve the formation of boron chloride species and subsequent cyclization with o-amino-styrene.
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| GB/T 7714 | Qiu, Weihua , Zhu, Jide , Tao, Rencai et al. Synthesis of 10B-enriched 2,1-borazaronaphthalenes from o-aminostyrenes and 10BF3 [J]. | ORGANIC CHEMISTRY FRONTIERS , 2024 , 11 (10) : 2733-2738 . |
| MLA | Qiu, Weihua et al. "Synthesis of 10B-enriched 2,1-borazaronaphthalenes from o-aminostyrenes and 10BF3" . | ORGANIC CHEMISTRY FRONTIERS 11 . 10 (2024) : 2733-2738 . |
| APA | Qiu, Weihua , Zhu, Jide , Tao, Rencai , Yang, Kai , Song, Qiuling . Synthesis of 10B-enriched 2,1-borazaronaphthalenes from o-aminostyrenes and 10BF3 . | ORGANIC CHEMISTRY FRONTIERS , 2024 , 11 (10) , 2733-2738 . |
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Abstract ：
Transition -metal -catalyzed asymmetric [2 + 2 + 2] cycloaddition of alkyne or nitrile motifs has received tremendous interest as it offers numerous possibilities to construct structurally diverse aromatic scaffolds with different chirality units. However, the use of these reactions is largely limited to symmetric alkynes, and the potential to use this strategy to design and construct chiral molecules is far from being explored. In this work, we report the transition -metal -catalyzed asymmetric [2 + 2 + 2] cycloaddition reactions of designed unsymmetric BN-diynes with nitriles or unsymmetric alkynes. This method offers practical access to the challenging atropisomers bearing a C -B axis with generally excellent regioselectivities and high enantioselectivities. Mechanistic studies revealed that the BN-naphthalenyl moiety of diynes is critical for the regioselectivity of this [2 + 2 + 2] cycloaddition.
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| GB/T 7714 | Wang, Hao , Qiao, Bolin , Zhu, Jide et al. Enantio- and regioselective [2+2+2] cycloaddition of BN-diynes for construction of C-B axial chirality [J]. | CHEM , 2024 , 10 (1) . |
| MLA | Wang, Hao et al. "Enantio- and regioselective [2+2+2] cycloaddition of BN-diynes for construction of C-B axial chirality" . | CHEM 10 . 1 (2024) . |
| APA | Wang, Hao , Qiao, Bolin , Zhu, Jide , Guo, Huosheng , Zhang, Zhen , Yang, Kai et al. Enantio- and regioselective [2+2+2] cycloaddition of BN-diynes for construction of C-B axial chirality . | CHEM , 2024 , 10 (1) . |
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In a recent issue of Chem, Chu, Gutierrez, and co-workers reported an enantioselective and stereodivergent three -compo-nent carbo-vinylation of alkenyl phosphonates to access chiral a-vinyl phosphonates via a combination of photocatalyst and chiral nickel catalyst.
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| GB/T 7714 | Yang, Kai , Song, Qiuling . Enantioselective three-component reaction to access chiral a-vinyl phosphonates [J]. | CHEM CATALYSIS , 2023 , 3 (3) . |
| MLA | Yang, Kai et al. "Enantioselective three-component reaction to access chiral a-vinyl phosphonates" . | CHEM CATALYSIS 3 . 3 (2023) . |
| APA | Yang, Kai , Song, Qiuling . Enantioselective three-component reaction to access chiral a-vinyl phosphonates . | CHEM CATALYSIS , 2023 , 3 (3) . |
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Alkynes are attractive synthons for organic chemistry. Despite the prevalence of transition-metal-catalyzed Sonogashira reactions, a transition-metal-free version of the arylation of terminal alkynes is elusive. Herein, we report an efficient transition-metal-free Sonogashira-type coupling reaction for the one-pot arylation of alkynes to construct C(sp)-C(sp2) bonds from a tetracoordinate boron intermediate with NIS as a mediator. With its high efficiency, wide substrate range, and good functional group tolerance, this method is further supported by the gram-scale synthesis and subsequent modification of complex molecules.
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| GB/T 7714 | Ye, Mingxing , Hou, Mengyuan , Wang, Yahao et al. Arylation of Terminal Alkynes: Transition-Metal-Free Sonogashira- Type Coupling for the Construction of C(sp)-C(sp2) Bonds [J]. | ORGANIC LETTERS , 2023 , 25 (10) : 1787-1792 . |
| MLA | Ye, Mingxing et al. "Arylation of Terminal Alkynes: Transition-Metal-Free Sonogashira- Type Coupling for the Construction of C(sp)-C(sp2) Bonds" . | ORGANIC LETTERS 25 . 10 (2023) : 1787-1792 . |
| APA | Ye, Mingxing , Hou, Mengyuan , Wang, Yahao , Ma, Xingxing , Yang, Kai , Song, Qiuling . Arylation of Terminal Alkynes: Transition-Metal-Free Sonogashira- Type Coupling for the Construction of C(sp)-C(sp2) Bonds . | ORGANIC LETTERS , 2023 , 25 (10) , 1787-1792 . |
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a-Haloboronates have a wide range of applications in organic chemistry as synthetic synthons; however, traditional synthetic methods of a-haloboronates are harsh and complicated. Herein, we used nBuLi as the nucleophilic reagent to attack the boron atom in gem-diborylalkanes to form tetracoordinate boron species and successfully achieved a-chloroboronates and a-bromoboronates with readily accessible electrophilic halogen reagents (NCS and NBS). The reaction is transition-metal-free and features a broad substrate scope and diversified valuable products.
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| GB/T 7714 | Liao, Shangteng , Liang, Jinchao , Li, Chaokun et al. Synthesis of a-Haloboronates by the Halogenation of gem-Diborylalkanes via Tetracoordinate Boron Species [J]. | ORGANIC LETTERS , 2023 , 25 (16) : 2928-2933 . |
| MLA | Liao, Shangteng et al. "Synthesis of a-Haloboronates by the Halogenation of gem-Diborylalkanes via Tetracoordinate Boron Species" . | ORGANIC LETTERS 25 . 16 (2023) : 2928-2933 . |
| APA | Liao, Shangteng , Liang, Jinchao , Li, Chaokun , Chen, Nan , Yang, Kai , Chen, Jinglong et al. Synthesis of a-Haloboronates by the Halogenation of gem-Diborylalkanes via Tetracoordinate Boron Species . | ORGANIC LETTERS , 2023 , 25 (16) , 2928-2933 . |
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Catalytic dynamic kinetic asymmetric transformation (DyKAT) provides a powerful tool to access chiral stereoisomers from racemic substrates. Such transformation has been widely employed on the construction of central chirality, however, the application in axial chirality remains underexplored because its equilibrium of substrate enantiomers is limited to five-membered metalacyclic intermediate. Here we report a tetracoordinate boron-directed dynamic kinetic asymmetric cross-coupling of racemic, configurationally stable 3-bromo-2,1-azaborines with boronic acid derivatives. A series of challenging C-B axially chiral compounds were prepared with generally good to excellent enantioselectivities. Moreover, this transformation can also be extended to prepare atropisomers bearing adjacent C-B and C-C diaxes with excellent diastereo- and enantio-control. The key to the success relies on the rational design of a reversible tetracoordinate boron intermediate, which is supported by theoretical calculations that dramatically reduces the rotational barrier of the original C-B axis and achieves the goal of DyKAT. The application of catalytic dynamic kinetic asymmetric transformation (DyKAT) in axial chirality is limited to fivemembered metalacyclic intermediate-directed equilibrium of substrate enantiomers. Here, the authors report a tetracoordinate boron-directed DyKAT of racemic, configurationally stable 3-bromo- 2,1-azaborines for the construction of C-B axial chirality.
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| GB/T 7714 | Yang, Kai , Mao, Yanfei , Zhang, Zhihan et al. Construction of C-B axial chirality via dynamic kinetic asymmetric cross-coupling mediated by tetracoordinate boron [J]. | NATURE COMMUNICATIONS , 2023 , 14 (1) . |
| MLA | Yang, Kai et al. "Construction of C-B axial chirality via dynamic kinetic asymmetric cross-coupling mediated by tetracoordinate boron" . | NATURE COMMUNICATIONS 14 . 1 (2023) . |
| APA | Yang, Kai , Mao, Yanfei , Zhang, Zhihan , Xu, Jie , Wang, Hao , He, Yong et al. Construction of C-B axial chirality via dynamic kinetic asymmetric cross-coupling mediated by tetracoordinate boron . | NATURE COMMUNICATIONS , 2023 , 14 (1) . |
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