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学者姓名：杨凯
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Abstract ：
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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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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The rapid recombination rate of photoexcited carriers for iron titanate (FeTiO3) is still limited the process performance of photo-Fenton. This article reports the successful synthesis of the highly efficient Z-scheme FeTiO3/MOF-derived In2S3 photocatalyst using the hydrothermal method, compensating for the susceptibility of FeTiO3 photo-generated carriers to complexation to a certain extent. A series of characterization have been carried out to explore the structure, morphology and composition of FeTiO3/MOF-derived In2S3 heterostructure. The 0.5 FeTiO3/MOF-derived In2S3 exhibits the excellent photo-Fenton performance for TCH, Cr6+ and OTC, the degradation rate constants (k(2)) are up to 0.6297 Lmg(-1)min(-1), 1.332 Lmg(-1)min(-1), and 0.427 Lmg(-1)min(-1), respectively. Active species capture experiments and electron paramagnetic resonance (EPR) spectra show that photo-generated holes (h(+)) and superoxide radicals (O-2(-)) are present in the photo-Fenton system. The superior photo-Fenton performance is mainly manifested in the following: the MOF-derived In2S3 micro-floral carrier extends the reaction interface of 0.5 FM-I; FeTiO3 effectively enhances the photo-absorption ability of 0.5 FM-I in visible range; the construction of Z-scheme FeTiO3/MOF-derived In2S3, forming the new carriers transport channels and enhancing the generation of O-2(-) and OH. This experimental exploration provided a reasonable experimental basis for the preparation of efficient photocatalysts.
Keyword ：
FeTiO3 FeTiO3 MOF-derived In2S3 MOF-derived In2S3 Photo-Fenton catalyst Photo-Fenton catalyst Z-scheme heterostructure Z-scheme heterostructure
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| GB/T 7714 | Chen, Jie , Liu, Yuanyuan , Luo, Xingrui et al. Construction of a novel Z-scheme FeTiO3/MOF-derived In2S3 catalyst for visible-light-driven photo-Fenton degradation of pollutants [J]. | JOURNAL OF ALLOYS AND COMPOUNDS , 2024 , 1008 . |
| MLA | Chen, Jie et al. "Construction of a novel Z-scheme FeTiO3/MOF-derived In2S3 catalyst for visible-light-driven photo-Fenton degradation of pollutants" . | JOURNAL OF ALLOYS AND COMPOUNDS 1008 (2024) . |
| APA | Chen, Jie , Liu, Yuanyuan , Luo, Xingrui , Qiu, Qingqing , Yang, Kai , Liang, Tongxiang . Construction of a novel Z-scheme FeTiO3/MOF-derived In2S3 catalyst for visible-light-driven photo-Fenton degradation of pollutants . | JOURNAL OF ALLOYS AND COMPOUNDS , 2024 , 1008 . |
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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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The catalytic asymmetric synthesis of axially chiral alkenes remains a daunting challenge due to the lower rotational barrier, especially for longer stereogenic axis (e.g. C-B axis). The asymmetric radical difunctionalization of alkynes represents an efficient strategy for these targets. Key to the success of such transformations lies in aryl-stabilized highly reactive alkenyl radical intermediates, however, it remains an elusive whether a boryl group could play a similar role. Here we report a nickel-catalyzed atroposelective radical relayed reductive coupling reaction of our designed ethynyl-azaborines with simple alkyl and aryl halides through a boron-stabilized vinyl radical intermediate. This transformation enables a straightforward access to the challenging axially chiral alkenylborons bearing a C-B axis in generally high enantioselectivity and excellent stereoselectivity. The catalytic asymmetric synthesis of axially chiral alkenes remains a challenge due to the lower rotational barrier, especially for longer stereogenic axis. Here the authors report a nickel-catalyzed atroposelective radical relayed reductive coupling reaction of ethynyl-azaborines with alkyl/aryl halides through a boron-stabilized vinyl radical intermediate.
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| GB/T 7714 | Qiu, Weihua , Tao, Rencai , He, Yong et al. Enantioselective construction of C-B axially chiral alkenylborons by nickel-catalyzed radical relayed reductive coupling [J]. | NATURE COMMUNICATIONS , 2024 , 15 (1) . |
| MLA | Qiu, Weihua et al. "Enantioselective construction of C-B axially chiral alkenylborons by nickel-catalyzed radical relayed reductive coupling" . | NATURE COMMUNICATIONS 15 . 1 (2024) . |
| APA | Qiu, Weihua , Tao, Rencai , He, Yong , Zhou, Yao , Yang, Kai , Song, Qiuling . Enantioselective construction of C-B axially chiral alkenylborons by nickel-catalyzed radical relayed reductive coupling . | NATURE COMMUNICATIONS , 2024 , 15 (1) . |
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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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Direct functionalization of 1,2-azaborines to construct B-C bonds remains challenging. Here, we report a Pd-catalyzed B-H aryl/alkenylation reaction of 1,2-azaborines. The method provides a general platform to access diverse boron-substituted 1,2-azaborine compounds (>60 examples). The synthetic utility is highlighted through the late-stage modification of bioactive molecules, as well as the preparation and transformations of the B-10-enriched 1,2-azaborine product and the synthesis of four BN isostere analogues of bioactive molecules. And the reaction mechanism is also explored and discussed.
Keyword ：
1,2-azaborines 1,2-azaborines B-H aryl/alkenylation B-H aryl/alkenylation B-Hbond transformation B-Hbond transformation mechanistic studies mechanistic studies palladium catalysis palladium catalysis
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| GB/T 7714 | Zhang, Zhen , Jiang, Dandan , Su, Peiwen et al. Pd-Catalyzed B-H Aryl/Alkenylation of 1,2-Azaborines [J]. | ACS CATALYSIS , 2024 , 14 (22) : 16996-17003 . |
| MLA | Zhang, Zhen et al. "Pd-Catalyzed B-H Aryl/Alkenylation of 1,2-Azaborines" . | ACS CATALYSIS 14 . 22 (2024) : 16996-17003 . |
| APA | Zhang, Zhen , Jiang, Dandan , Su, Peiwen , Yang, Kai , Yu, Peiyuan , Song, Qiuling . Pd-Catalyzed B-H Aryl/Alkenylation of 1,2-Azaborines . | ACS CATALYSIS , 2024 , 14 (22) , 16996-17003 . |
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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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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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The incorporation of alkenylboronates into axially chiral compounds increases their structural diversity and provides a synthetic handle for late-stage functionalizations. Despite advances made in the synthesis of axially chiral acyclic alkenes, catalytic enantioselective synthesis of tetrasubstituted axially chiral acyclic alkenylboronates still remains a challenge. Here, we report a combined copper- and palladium-catalysed atroposelective arylboration of alkynes, providing access to tetrasubstituted axially chiral alkenylboronates. The process can tolerate a broad range of functional groups and substrates, including unsymmetrical alkynes, providing products with excellent Z-/E-selectivity, regiocontrol and enantiocontrol. The synthetic use of the products has been demonstrated through onwards synthetic transformations to generate various new axially chiral olefins including axially chiral 1,3-enynes. Mechanistic experiments reveal a potential combined copper and palladium catalytic cycle, with the observed stereocontrol originating from a higher-order active palladium catalyst. [Figure not available: see fulltext.] © 2023, The Author(s), under exclusive licence to Springer Nature Limited.
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| GB/T 7714 | Li, W. , Chen, S. , Xie, J. et al. Synthesis of axially chiral alkenylboronates through combined copper- and palladium-catalysed atroposelective arylboration of alkynes [J]. | Nature Synthesis , 2023 , 2 (2) : 140-151 . |
| MLA | Li, W. et al. "Synthesis of axially chiral alkenylboronates through combined copper- and palladium-catalysed atroposelective arylboration of alkynes" . | Nature Synthesis 2 . 2 (2023) : 140-151 . |
| APA | Li, W. , Chen, S. , Xie, J. , Fan, Z. , Yang, K. , Song, Q. . Synthesis of axially chiral alkenylboronates through combined copper- and palladium-catalysed atroposelective arylboration of alkynes . | Nature Synthesis , 2023 , 2 (2) , 140-151 . |
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