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学者姓名：宋秋玲
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Abstract ：
Chiral five-membered cyclic tertiary alcohols are important structural motifs in functional materials, pharmaceuticals, and bioactive molecules. Hence, developing efficient methodologies for synthesizing compounds featuring these privileged scaffolds represents a crucial pursuit within synthetic chemistry. Herein, we present a regio- and enantioselective Ni-catalyzed strategy for the reductive [3 + 2] annulation of beta-bromoenones with alkynes, providing convenient access to chiral five-membered cyclic tertiary alcohols with high levels of regio-, and enantioselectivity via axial chirality transfer to central chirality. The utilization of an environmentally sustainable bis(pinacolato)diboron (B(2)pin(2)) is crucial for the success of this asymmetric reductive cyclization reaction. Simultaneously, the mild reaction environment greatly enhances functional group compatibility. This has been demonstrated by the broad substrate scope, late-stage functionalizations of bioactive compounds or drug molecules, and subsequent transformations. Amongst, it is worth emphasizing that these functionally enriched chiral five-membered cyclic tertiary alcohols can efficiently participate in Diels-Alder reactions to synthesize enantioenriched polycyclic and heterocyclic molecules, thereby further validating the significance of introducing a cyclopentadiene skeleton. The preliminary mechanistic studies revealed the mode of action of B(2)pin(2) in mononuclear Ni-catalyzed asymmetric reductive [3 + 2] annulation reactions and density functional theory (DFT) calculations clarified the origin of the experimentally observed regio- and enantioselectivity.
Keyword ：
B(2)pin(2) as reductant B(2)pin(2) as reductant Chiral tertiary alcohols Chiral tertiary alcohols Enantioselectivity Enantioselectivity Nickel Nickel Reductive [3+2] annulation Reductive [3+2] annulation
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| GB/T 7714 | Li, Wangyang , Zheng, Yanping , Gu, Yunya et al. Bis(pinacolato)Diboron-Enabled Nickel-Catalyzed Regio- and Enantioselective Reductive [3+2] Annulation of β-Bromoenones with Alkynes [J]. | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION , 2025 . |
| MLA | Li, Wangyang et al. "Bis(pinacolato)Diboron-Enabled Nickel-Catalyzed Regio- and Enantioselective Reductive [3+2] Annulation of β-Bromoenones with Alkynes" . | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2025) . |
| APA | Li, Wangyang , Zheng, Yanping , Gu, Yunya , Cheng, Shanshan , Xie, Jinhui , Lu, Yong et al. Bis(pinacolato)Diboron-Enabled Nickel-Catalyzed Regio- and Enantioselective Reductive [3+2] Annulation of β-Bromoenones with Alkynes . | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION , 2025 . |
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The synthesis of polycyclic indoles is significant in organic chemistry, due to such heterocyclic frameworks being present in numerous bioactive pharmaceuticals and natural alkaloids. Herein, we provide an efficient radical cascade cyclization strategy to generate indole-fused diazepine derivatives using phosphoryl or sulfonyl radicals with N-(2-(1H-indol-1-yl)phenyl)-N-methylmethacrylamides. The merits of this synthesis are attributed to its accessible starting materials, broad substrate compatibility and excellent diastereoselectivity.
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| GB/T 7714 | Wang, Yutong , Huang, Xiujuan , Chen, Jinglong et al. Diastereoselective radical cascade cyclization to access indole-fused diazepine derivatives [J]. | ORGANIC & BIOMOLECULAR CHEMISTRY , 2025 , 23 (18) : 4349-4354 . |
| MLA | Wang, Yutong et al. "Diastereoselective radical cascade cyclization to access indole-fused diazepine derivatives" . | ORGANIC & BIOMOLECULAR CHEMISTRY 23 . 18 (2025) : 4349-4354 . |
| APA | Wang, Yutong , Huang, Xiujuan , Chen, Jinglong , Xu, Jian , Song, Qiuling . Diastereoselective radical cascade cyclization to access indole-fused diazepine derivatives . | ORGANIC & BIOMOLECULAR CHEMISTRY , 2025 , 23 (18) , 4349-4354 . |
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In the past decades, chiral sp3-geminated bimetallic reagents based on B, Si, and Sn have drawn much attention due to their unique structure and the potential for iterative multifold transformations, thus efficiently increasing the molecular complexity. However, the asymmetric preparation of such reagents is highly challenging and new synthetic approaches are still in demand. This review provides a brief overview of the synthesis of nonracemic gem-borylstannyl, gem-borylsilyl, and gem-diboryl compounds, and is organized according to the types of gem-bimetallic reagents and their corresponding synthetic strategies.
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| GB/T 7714 | Li, Xin , Song, Qiuling . Asymmetric synthesis of chiral sp3-geminated borylstannyl, borylsilyl, and diboryl compounds [J]. | ORGANIC CHEMISTRY FRONTIERS , 2025 , 12 (9) : 3129-3142 . |
| MLA | Li, Xin et al. "Asymmetric synthesis of chiral sp3-geminated borylstannyl, borylsilyl, and diboryl compounds" . | ORGANIC CHEMISTRY FRONTIERS 12 . 9 (2025) : 3129-3142 . |
| APA | Li, Xin , Song, Qiuling . Asymmetric synthesis of chiral sp3-geminated borylstannyl, borylsilyl, and diboryl compounds . | ORGANIC CHEMISTRY FRONTIERS , 2025 , 12 (9) , 3129-3142 . |
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Domino cascade reactions, which can construct multiple bonds in one pot, are efficient methods to synthesize N-heterocycles and other useful skeletons. Herein, we report an expedient synthesis of polysubstituted benzo[b][1,5]naphthyridine via Mn(III)-mediated C-C bond cleavage of cyclopropanols. These reactions were initiated by addition of beta-carbonyl radicals, generated from cyclopropyl alcohols in the presence of Mn(III), to 2-(2-isocyanophenyl)acetonitriles to give quinolin-3-amines, which went through intramolecular cyclizations and dehydrogenation to give the final products.
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| GB/T 7714 | Mu, Shiqiang , Xuan, Qingqing , Luo, Ying et al. Synthesis of Polysubstituted Benzo[b][1,5]naphthyridine via Mn(III)-Mediated Domino Cascade Reactions of Cyclopropanols and 2-(2-Isocyanophenyl)acetonitriles [J]. | ORGANIC LETTERS , 2025 , 27 (1) : 153-158 . |
| MLA | Mu, Shiqiang et al. "Synthesis of Polysubstituted Benzo[b][1,5]naphthyridine via Mn(III)-Mediated Domino Cascade Reactions of Cyclopropanols and 2-(2-Isocyanophenyl)acetonitriles" . | ORGANIC LETTERS 27 . 1 (2025) : 153-158 . |
| APA | Mu, Shiqiang , Xuan, Qingqing , Luo, Ying , Guo, Yu , Xu, Jian , Song, Qiuling . Synthesis of Polysubstituted Benzo[b][1,5]naphthyridine via Mn(III)-Mediated Domino Cascade Reactions of Cyclopropanols and 2-(2-Isocyanophenyl)acetonitriles . | ORGANIC LETTERS , 2025 , 27 (1) , 153-158 . |
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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 (B(2)pin(2)) or alkenyl boron (alkenylBpin) react with o-bromostyrenes 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 1,6-remote 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 Csp(3)-B and Csp(2)-B bonds obtained simultaneously with B(2)pin(2) or portrays alkenyl-migrative module and excellent E/Z selectivity with alkenylBpins. [GRAPHICS] .
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 , 2025 , 7 (1) : 279-292 . |
| MLA | Li, Chaokun et al. "Remote Boryl and Alkenyl Radical Migration of Olefin-Bearing Aryl Bromides" . | CCS CHEMISTRY 7 . 1 (2025) : 279-292 . |
| 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 , 2025 , 7 (1) , 279-292 . |
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Although representing an atom- and step-economic access to aromatic nitrile-containing compounds, the denitrogenative transformations of 3-aminoindazoles are highly challenging due to high C-N bond dissociation energy, stable five-membered heterocycles, and selective cleavage of two C-N bonds in one step. Only in recent years have chemists addressed the reactivity and selectivity issues of this reaction. By virtue of which, a diverse array of structurally novel compounds have been synthesized in good yields. This chapter summarizes and discusses the recent advances in denitrogenative transformations of 3-aminoindazoles, which include coupling with conjugated unsaturated systems, coupling with thiols and diselenides, denitrogenative transannulation, and N-N bond cleavage of 3-aminoindazoles. © 2025 WILEY-VCH GmbH.
Keyword ：
3-Aminoindazoles 3-Aminoindazoles arenes arenes C-N bond cleavage C-N bond cleavage copper copper denitrogenation denitrogenation diselenides diselenides enamines enamines heterocycles heterocycles ketene dithioacetals ketene dithioacetals N-N bond cleavage N-N bond cleavage radical radical thiols thiols transannulation transannulation
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| GB/T 7714 | Li, X. , Song, Q. . Denitrogenative Transformations of 3-Aminoindazoles [未知]. |
| MLA | Li, X. et al. "Denitrogenative Transformations of 3-Aminoindazoles" [未知]. |
| APA | Li, X. , Song, Q. . Denitrogenative Transformations of 3-Aminoindazoles [未知]. |
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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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Herein, we report a ligand-controlled palladium-catalyzed method that enables the synthesis of ynones and gamma-butenolides with excellent regioselectivity from the same set of readily available aryl iodides, aryl acetylenes, and BrCF2CO2K. In this reaction, the [Pd-II]CF2 does demonstrate electrophilicity and can generate CO readily when reacting with H2O. It is environmentally friendly and safe compared to traditional methods, and the current protocol enables us to afford ynones and gamma-butenolides in high yields with excellent functionality tolerance. Moreover, esters can also be obtained with corresponding phenols and alcohols utilizing this strategy. The success of late-stage functionalization of bioactive compounds further illustrates the synthetic utility of this protocol in material development and drug discovery.
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| GB/T 7714 | Sheng, Heyun , Chen, Zhiwei , Song, Qiuling . Palladium-Catalyzed Difluorocarbene Transfer Enabled Divergent Synthesis of γ-Butenolides and Ynones from Iodobenzene and Terminal Alkynes [J]. | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 2024 , 146 (2) : 1722-1731 . |
| MLA | Sheng, Heyun et al. "Palladium-Catalyzed Difluorocarbene Transfer Enabled Divergent Synthesis of γ-Butenolides and Ynones from Iodobenzene and Terminal Alkynes" . | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 146 . 2 (2024) : 1722-1731 . |
| APA | Sheng, Heyun , Chen, Zhiwei , Song, Qiuling . Palladium-Catalyzed Difluorocarbene Transfer Enabled Divergent Synthesis of γ-Butenolides and Ynones from Iodobenzene and Terminal Alkynes . | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 2024 , 146 (2) , 1722-1731 . |
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The pi-bond enrichment frameworks not only serve as a crucial building block in organic synthesis but also assume a pivotal role in the fields of materials science, biomedicine, photochemistry, and other related disciplines owing to their distinctive structural characteristics. The incorporation of various substituents into the C & boxH;C double bonds of tetrasubstituted alkenes is currently a highly significant research area. However, the synthesis of tetrasubstituted alkenes with diverse substituents on double bonds poses a significant challenge in achieving stereoselectivity. Here, we reported an efficient and convergent route of Cu-catalyzed borylalkynylation of both symmetrical and unsymmetrical 1,3-diynes, B(2)pin(2), and acetylene bromide to the construction of boronated phenyldiethynylethylene (BPDEE) derivatives with excellent chemo-, stereo-, and regioselectivities. BPDEE derivatives could transform into novel tetrasubstituted organic pi-conjugated gem-diphenyldiethynylethylene (DPDEE), vinylphenyldiethynylethylene (VPDEE), and phenyltriethynylethylene (PTEE) derivatives by a stepwise process, which provides a flexible platform for the synthesis of complex pi-bond enrichment frameworks that were difficult to synthesize by previous methods. The initial optical characterization revealed that the synthesized molecules exhibited aggregation-induced emission (AIE) properties, which further establishes the groundwork for future applications and enriches and advances the field of functional pi-conjugated frameworks research.
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| GB/T 7714 | Xie, Jinhui , Li, Wangyang , Lu, Yong et al. Unlocking Diverse π-Bond Enrichment Frameworks by the Synthesis and Conversion of Boronated Phenyldiethynylethylenes [J]. | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 2024 , 146 (14) : 10167-10176 . |
| MLA | Xie, Jinhui et al. "Unlocking Diverse π-Bond Enrichment Frameworks by the Synthesis and Conversion of Boronated Phenyldiethynylethylenes" . | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 146 . 14 (2024) : 10167-10176 . |
| APA | Xie, Jinhui , Li, Wangyang , Lu, Yong , Zheng, Yanping , Huang, Yanying , Chen, Shanglin et al. Unlocking Diverse π-Bond Enrichment Frameworks by the Synthesis and Conversion of Boronated Phenyldiethynylethylenes . | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 2024 , 146 (14) , 10167-10176 . |
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The first three-component cyclization reaction of benzo[c][1,2]dithiol-3-ones based on S-S bond cleavage is disclosed herein. A range of 2,3-dihydrobenzothiazin-4-ones were achieved in decent yields under mild conditions. The current synthesis route features advantages such as simple operation, readily available raw materials, transition-metal-free conditions, no protection of inert gases, good yields, excellent functional group compatibility and accessible scalability. The first three-component cyclization reaction of benzo[c][1,2]dithiol-3-ones based on S-S bond cleavage is disclosed herein.
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| GB/T 7714 | Zhang, Guan , Wan, Huimin , Dong, Na et al. Metal-free three-component tandem cyclization for modular synthesis of 2,3-dihydrobenzothiazin-4-ones [J]. | ORGANIC CHEMISTRY FRONTIERS , 2024 , 11 (7) : 2021-2026 . |
| MLA | Zhang, Guan et al. "Metal-free three-component tandem cyclization for modular synthesis of 2,3-dihydrobenzothiazin-4-ones" . | ORGANIC CHEMISTRY FRONTIERS 11 . 7 (2024) : 2021-2026 . |
| APA | Zhang, Guan , Wan, Huimin , Dong, Na , Zhu, Antong , Zhou, Yao , Song, Qiuling . Metal-free three-component tandem cyclization for modular synthesis of 2,3-dihydrobenzothiazin-4-ones . | ORGANIC CHEMISTRY FRONTIERS , 2024 , 11 (7) , 2021-2026 . |
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