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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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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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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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Organophosphorus compounds are extensively utilized in the field of medicine, materials, life sciences, and organic synthesis, among which chiral phosphorus compounds are the most widely used. Therefore, the construction of chiral phosphorus centers has always been the hotspot and challenge in organic synthesis. Traditional synthesis methods are mainly focused on chiral resolution and chiral induction strategies. Recently, the construction of chiral phosphorus centers via asymmetric catalysis has been well developed. The recently development of desymmetrization strategies in the construction of phos- phorus centers is summarized, mainly focused on the transformation of C—H, C=C, C≡C bonds and hydroxyl group. What’s more, the deficiencies of current strategies and the trends of future development have also been discussed. © 2024 Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences.
Keyword ：
C—H bond activation C—H bond activation desymmetrization desymmetrization P-stereogenic center P-stereogenic center
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| GB/T 7714 | Lin, G. , Xu, J. , Song, Q. . Recent Advances in the Synthesis of P-Stereogenic Compounds via Desymmetrization Strategy; [基于去对称化策略合成磷中心手性化合物的研究进展] [J]. | Chinese Journal of Organic Chemistry , 2024 , 44 (12) : 3621-3638 . |
| MLA | Lin, G. et al. "Recent Advances in the Synthesis of P-Stereogenic Compounds via Desymmetrization Strategy; [基于去对称化策略合成磷中心手性化合物的研究进展]" . | Chinese Journal of Organic Chemistry 44 . 12 (2024) : 3621-3638 . |
| APA | Lin, G. , Xu, J. , Song, Q. . Recent Advances in the Synthesis of P-Stereogenic Compounds via Desymmetrization Strategy; [基于去对称化策略合成磷中心手性化合物的研究进展] . | Chinese Journal of Organic Chemistry , 2024 , 44 (12) , 3621-3638 . |
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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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The enantioselective introduction of gem-difluorinated carbonyl (i. e. α,α-difluoro carbonyl) moieties into organic structures is a synthetically valuable but highly challenging approach. During the past decades, continuous efforts have been made for the developments of synthetic strategies for constructing C(sp3)−CF2COR chiral centers with high levels of enantioselectivities. This review summarizes and discusses the recent advance in the enantioselective construction of gem-difluorinated carbonyl moieties, which are organized according to the reaction categories. © 2024 Wiley-VCH GmbH.
Keyword ：
Fluorine Fluorine gem-difluorinated carbonyl gem-difluorinated carbonyl Lewis acid Lewis acid organocatalysis organocatalysis photoredox photoredox
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| GB/T 7714 | Li, X. , Song, Q. . Recent Advances in the Enantioselective Construction of gem-Difluorinated Carbonyl Moieties [J]. | Advanced Synthesis and Catalysis , 2024 , 366 (16) : 3405-3416 . |
| MLA | Li, X. et al. "Recent Advances in the Enantioselective Construction of gem-Difluorinated Carbonyl Moieties" . | Advanced Synthesis and Catalysis 366 . 16 (2024) : 3405-3416 . |
| APA | Li, X. , Song, Q. . Recent Advances in the Enantioselective Construction of gem-Difluorinated Carbonyl Moieties . | Advanced Synthesis and Catalysis , 2024 , 366 (16) , 3405-3416 . |
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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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Due to the high reactivity and versatility of benzenesulfonothioates, significant advancements have been made in constructing C-S bonds. However, there are certain limitations in the synthesis of S-thiosulfonates and SS-thiosulfonates, especially when dealing with substantial steric hindrance, which poses a significant challenge. Herein, we present an innovative approach for assembling unsymmetric S-thiosulfonates and unsymmetric SS-thiosulfonates through the integration of dual copper/photoredox catalysis. Moreover, we also realized the one-pot strategy by directly using carboxylic acids as raw materials by in-situ activation of them to access S-thiosulfonates and SS-thiosulfonates without further purification and presynthesis of NHPI esters. The envisaged synthesis and utilization of these reagents are poised to pioneer an innovative pathway for fabricating a versatile spectrum of mono-, di-, and polysulfide compounds. Furthermore, they introduce a class of potent sulfenylating reagents, empowering the synthesis of intricate unsymmetrical disulfides that were previously challenging to access. © The Author(s) 2024.
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| GB/T 7714 | Guo, Y. , Lin, G. , Zhang, M. et al. Photo-induced decarboxylative C-S bond formation to access sterically hindered unsymmetric S-alkyl thiosulfonates and SS-alkyl thiosulfonates [J]. | Nature Communications , 2024 , 15 (1) . |
| MLA | Guo, Y. et al. "Photo-induced decarboxylative C-S bond formation to access sterically hindered unsymmetric S-alkyl thiosulfonates and SS-alkyl thiosulfonates" . | Nature Communications 15 . 1 (2024) . |
| APA | Guo, Y. , Lin, G. , Zhang, M. , Xu, J. , Song, Q. . Photo-induced decarboxylative C-S bond formation to access sterically hindered unsymmetric S-alkyl thiosulfonates and SS-alkyl thiosulfonates . | Nature Communications , 2024 , 15 (1) . |
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A protocol for the synthesis of alpha-alkenylated tetrahydropyrans (THPs) with 3,4-dihydro-2H-pyran derivatives and potassium alkenyltrifluoroborates was achieved in the presence of a Bronsted acid and a Lewis acid under mild reaction conditions. The oxonium ion intermediates, produced from various readily available 3,4-dihydro-2H-pyran derivatives, were attacked by the nucleophile to form the desired alpha-alkenylated products. This strategy could be an alternative approach to modify a series of modules that are of broad utility in natural products and fine chemicals.
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| GB/T 7714 | Chen, Nan , Li, Chaokun , Liao, Shangteng et al. Brønsted acid-mediated selective α-alkenylation of 3,4-dihydro-2H-pyrans [J]. | ORGANIC CHEMISTRY FRONTIERS , 2024 , 11 (16) : 4402-4407 . |
| MLA | Chen, Nan et al. "Brønsted acid-mediated selective α-alkenylation of 3,4-dihydro-2H-pyrans" . | ORGANIC CHEMISTRY FRONTIERS 11 . 16 (2024) : 4402-4407 . |
| APA | Chen, Nan , Li, Chaokun , Liao, Shangteng , Chen, Jinglong , Ma, Xingxing , Song, Qiuling . Brønsted acid-mediated selective α-alkenylation of 3,4-dihydro-2H-pyrans . | ORGANIC CHEMISTRY FRONTIERS , 2024 , 11 (16) , 4402-4407 . |
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