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学者姓名：宋秋玲
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Abstract ：
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. 等. "Denitrogenative Transformations of 3-Aminoindazoles" [未知]. |
| APA | Li, X. , Song, Q. . Denitrogenative Transformations of 3-Aminoindazoles [未知]. |
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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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Herein, we report a distinctive and marvelous dual-migration of alkynyl tetracoordinate borons activated by both hydrochloric acid (HCl) and N-chlorosuccinimide (NCS), which is significantly different from conventional migration modes under basic conditions. In this protocol, HCl, as the first electrophile, activates the C equivalent to C bond, triggering the first 1,2-aryl migration. Subsequently, NCS promotes a secondary metallate shift, enabling the construction of polysubstituted alkenes. Notably, this process can work well under mild conditions, exhibits high efficiency, and provides valuable products. This transformation reveals that Zweifel olefination is not just limited to traditional basic conditions, it can proceed smoothly under acidic conditions as well, which greatly expands the scope of this well-known olefination reaction.
Keyword ：
distinct electrophile distinct electrophile dual migrations dual migrations multi-substituted olefins multi-substituted olefins tetracoordinate borons tetracoordinate borons
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| GB/T 7714 | An, Hejun , Zhu, Wei , Tan, Mengwei et al. Two distinct electrophiles enabled sequential dual migrations of alkynyl tetracoordinate borons [J]. | SCIENCE CHINA-CHEMISTRY , 2025 . |
| MLA | An, Hejun et al. "Two distinct electrophiles enabled sequential dual migrations of alkynyl tetracoordinate borons" . | SCIENCE CHINA-CHEMISTRY (2025) . |
| APA | An, Hejun , Zhu, Wei , Tan, Mengwei , Cai, Meihui , Huang, Yi , Ma, Xingxing et al. Two distinct electrophiles enabled sequential dual migrations of alkynyl tetracoordinate borons . | SCIENCE CHINA-CHEMISTRY , 2025 . |
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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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Multiboronated compounds play more and more significant roles in the chemical community, and 1,1,1-triborylalkanes have emerged as versatile building blocks in organic synthesis. However, efficient strategies for the assembly of such compounds are very rare. A general and atom-economical synthesis of 1,1,1-triborylalkanes from various alkenes with pinacolborane (HBpin) is reported for the first time. The success of this transformation relies on the use of the commercially available Schwartz reagent (Cp2ZrHCl) as a catalyst, enabling sequential dehydrogenative borylation and hydroboration. This reaction demonstrates excellent selectivity, high yields, and broad functional group tolerance. Mechanistic investigations reveal that the process begins with two consecutive dehydrogenative borylations catalyzed by zirconium, producing a 1,1-diborylalkene intermediate, which subsequently undergoes hydroboration with HBpin to afford 1,1,1-triborylalkanes. Notably, this approach allows for remote 1,1,1-triboration of internal alkenes.
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| GB/T 7714 | Liu, Kang , Liang, Menghan , Song, Qiuling . Zr-Catalyzed Assembly of 1,1,1-Triborylalkanes from Alkenes and HBpin [J]. | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 2025 , 147 (20) : 17539-17548 . |
| MLA | Liu, Kang et al. "Zr-Catalyzed Assembly of 1,1,1-Triborylalkanes from Alkenes and HBpin" . | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 147 . 20 (2025) : 17539-17548 . |
| APA | Liu, Kang , Liang, Menghan , Song, Qiuling . Zr-Catalyzed Assembly of 1,1,1-Triborylalkanes from Alkenes and HBpin . | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 2025 , 147 (20) , 17539-17548 . |
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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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The enantioselective synthesis of boron-stereogenic compounds remains a formidable challenge in modern synthetic chemistry due to the limited availability of efficient catalytic strategies. Herein, we report an N-heterocyclic carbene (NHC)-catalyzed kinetic resolution of 3-formyl BODIPYs, which provides access to enantioenriched 3-formyl BODIPYs and aryl 3-carboxylate BODIPYs in good to high yields with high enantioselectivities (up to 96% ee). This method features a broad substrate scope, mild reaction conditions, and exceptional functional group tolerance. Furthermore, the resulting chiral BODIPYs exhibit promising circularly polarized luminescence properties. This work represents the successful application of NHC catalysis for constructing boron-stereogenic centers, expanding the toolbox for asymmetric organocatalysis.
Keyword ：
asymmetricsynthesis asymmetricsynthesis boron-stereogenic BODIPYs boron-stereogenic BODIPYs esterification esterification kinetic resolution kinetic resolution N-heterocyclic carbenes N-heterocyclic carbenes
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| GB/T 7714 | Gao, Yuan-Yuan , Liang, Yu-Jing , Li, Gaowei et al. NHC-Catalyzed Kinetic Resolution for the Synthesis of Boron-Stereogenic BODIPYs [J]. | ACS CATALYSIS , 2025 , 15 (11) : 9346-9352 . |
| MLA | Gao, Yuan-Yuan et al. "NHC-Catalyzed Kinetic Resolution for the Synthesis of Boron-Stereogenic BODIPYs" . | ACS CATALYSIS 15 . 11 (2025) : 9346-9352 . |
| APA | Gao, Yuan-Yuan , Liang, Yu-Jing , Li, Gaowei , Li, Lu , Hu, Zhi-Yuan , Lin, Wen-Hao et al. NHC-Catalyzed Kinetic Resolution for the Synthesis of Boron-Stereogenic BODIPYs . | ACS CATALYSIS , 2025 , 15 (11) , 9346-9352 . |
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A copper-catalyzed sequential hydroboration/isomerization/boryldemetalation reaction of arylidenecyclopropanes (ACPs) is reported, furnishing a straightforward and efficient route for the assembly of valuable 1,3-diboronates featuring both sp(2)/sp(3) C-B bonds. In contrast to the established CuH-induced ring-opening cascade hydrofunctionalizations of ACPs, which afford diverse sp(3)/sp(3) 1,n-diboronates, silylboronates, or aminoboronates, CuBpin species-catalyzed diborylation variant remains unexplored. Particularly, the envisioned ring-opening regioselective hydroboration followed by boryldemetalation of homoallylic copper intermediates to concurrently construct both sp(2)- and sp(3)-hybridized C-B bonds in a one-pot transformation represents a significant knowledge gap in this field. Herein, we present the Cu-catalyzed chemo-, regio-, and stereoselective ring-opening sp(2)/sp(3) diborylation of ACPs. Control experiments are conducted to illustrate the flexible transformation of Cu-H into Cu-Bpin and the essential significance of NaBEt3H in this transformation. The synthetic practicality of our presented protocol is further demonstrated by gram-scale preparation within a short period and the selective derivatization of the two types of boron moieties, enabling access to diversified high-valued 1,n-diboron compounds (n = 3, 5, 6), beta-hydroxy ketones, 1,3-diols, alpha,beta-unsaturated ketones, thermodynamically unstable cis-homoallylic boronate, and cis-homoallylic alcohol.
Keyword ：
copper-catalyzed copper-catalyzed Cu-Bpin Cu-Bpin diverse diboronates diverse diboronates NaBEt(3)Has activator NaBEt(3)Has activator sp(2)/sp(3) diborylation of ACPs sp(2)/sp(3) diborylation of ACPs Z-olefins Z-olefins
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| GB/T 7714 | Chen, Shanglin , Lin, Junmei , Song, Qiuling . Copper-Catalyzed Chemo-, Regio-, and Stereoselective Ring-Opening sp2/sp3 Diborylation of Arylidenecyclopropanes [J]. | ACS CATALYSIS , 2025 , 15 (15) : 13003-13014 . |
| MLA | Chen, Shanglin et al. "Copper-Catalyzed Chemo-, Regio-, and Stereoselective Ring-Opening sp2/sp3 Diborylation of Arylidenecyclopropanes" . | ACS CATALYSIS 15 . 15 (2025) : 13003-13014 . |
| APA | Chen, Shanglin , Lin, Junmei , Song, Qiuling . Copper-Catalyzed Chemo-, Regio-, and Stereoselective Ring-Opening sp2/sp3 Diborylation of Arylidenecyclopropanes . | ACS CATALYSIS , 2025 , 15 (15) , 13003-13014 . |
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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. Multi-component cascade transformations including difunctionalization of two alkynes with both syn- and anti-selectivity in one catalyst system is challenging. Herein, the authors report a Nickel-catalyzed four-component reaction to access densely substituted 1,3-dienes using two terminal alkynes, aryl boroxines, and perfluoroalkyl iodides.
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| GB/T 7714 | Chen, Shanglin , Wang, Ya-Nan , Xie, Jinhui 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, Shanglin 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, Shanglin , Wang, Ya-Nan , Xie, Jinhui , Li, Wangyang , Ye, Mingxing , Ma, Xingxing 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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