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学者姓名：宋秋玲
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Abstract ：
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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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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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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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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Herein, we report an expedient synthesis of fused phosphorus-containing heterocycles via Rh-catalyzed cascade C-H activation, alkyne insertion, and lactonization reactions. The substrate scope and the group tolerance are good, as various substituted benzoic acids, N-methoxybenzamides, and 2-phenylindoles could go through the reactions smoothly to afford the corresponding products in moderate to high yields. Additionally, excellent regioselectivities are shown in the alkyne insertion with the assistance of an electron-withdrawing phosphonate group.
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| GB/T 7714 | Yang, Yingying , Chen, Menghan , Xuan, Qingqing et al. Rh(III)-Catalyzed Regioselective Alkyne Insertion in the Context of C-H Activation and Lactonization Reactions: Synthesis of Fused 1,2-Oxaphospholenes [J]. | ORGANIC LETTERS , 2024 , 26 (36) : 7683-7687 . |
| MLA | Yang, Yingying et al. "Rh(III)-Catalyzed Regioselective Alkyne Insertion in the Context of C-H Activation and Lactonization Reactions: Synthesis of Fused 1,2-Oxaphospholenes" . | ORGANIC LETTERS 26 . 36 (2024) : 7683-7687 . |
| APA | Yang, Yingying , Chen, Menghan , Xuan, Qingqing , Xu, Jian , Song, Qiuling . Rh(III)-Catalyzed Regioselective Alkyne Insertion in the Context of C-H Activation and Lactonization Reactions: Synthesis of Fused 1,2-Oxaphospholenes . | ORGANIC LETTERS , 2024 , 26 (36) , 7683-7687 . |
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Asymmetric synthesis based on a metallate shift of tetracoordinate borons is an intriguing and challenging topic. Despite the construction of central chirality from tetracoordinate boron species via a 1,2-metallate shift, catalytic asymmetric synthesis of axially chiral compounds from such boron 'ate' complexes is an ongoing challenge. Axially chiral alkenes have received great attention due to their unique characteristics and intriguing molecular scaffolds. Here we report an enantioselective nickel-catalysed strategy for the construction of axially chiral alkenes via a 1,3-metallate shift of alkynyl tetracoordinate boron species. The chemoselectivity, regioselectivity and atroposelectivity can be regulated and well-controlled from readily accessible starting materials with a cheap transition-metal catalyst. Downstream transformations indicate the powerful conversion ability of such compounds in this protocol, and late-stage elaborations of bioactive compounds can also be achieved. Mechanistic experiments reveal that regioselective syn-addition of an aryl-Ni complex with a carbon-carbon triple bond and subsequent 1,3-phenyl migration are the two key steps for the synthesis of axially chiral alkenes. Enantioselective transformations based on tetracoordinate borons are elusive. Now, an enantioselective nickel-catalysed strategy for the construction of axially chiral alkenes has been reported, via a 1,3-metallate shift of alkynyl tetracoordinate boron species. The reaction uses readily accessible starting materials and a cheap transition-metal catalyst, and the chemoselectivity, regioselectivity and atroposelectivity could be well controlled.
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| GB/T 7714 | Ma, Xingxing , Tan, Mengwei , Li, Luo et al. Ni-catalysed assembly of axially chiral alkenes from alkynyl tetracoordinate borons via 1,3-metallate shift [J]. | NATURE CHEMISTRY , 2024 , 16 (1) . |
| MLA | Ma, Xingxing et al. "Ni-catalysed assembly of axially chiral alkenes from alkynyl tetracoordinate borons via 1,3-metallate shift" . | NATURE CHEMISTRY 16 . 1 (2024) . |
| APA | Ma, Xingxing , Tan, Mengwei , Li, Luo , Zhong, Zihao , Li, Puhui , Liang, Jinchao et al. Ni-catalysed assembly of axially chiral alkenes from alkynyl tetracoordinate borons via 1,3-metallate shift . | NATURE CHEMISTRY , 2024 , 16 (1) . |
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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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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 , 16 (8) . |
| MLA | Su, Wanlan et al. "Copper-catalysed asymmetric hydroboration of alkenes with 1,2-benzazaborines to access chiral naphthalene isosteres" . | NATURE CHEMISTRY 16 . 8 (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 , 16 (8) . |
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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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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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