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Synthesis of chiral phosphine derivatives through a copper（I）-catalyzed desymmetric SNAr reaction

Science China chemistry 2025年

作者： Shuai Zhang Pei-Zhi Liu Yan-Bo Li Qi Zhang Jun-Zhao Xiao Yi-Fan Wang Tian-Yu Wei Jia-Wei Jiang Ye Wang Qian Peng Liang Yin Key Laboratory of Fluorine and Nitrogen chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences State Key Laboratory of elemento-organic chemistry and Tianjin Key Laboratory of Biosensing and Molecular Recognition College of Chemistry Frontiers Science Center for New Organic Matter Nankai University Haihe Laboratory of Sustainable Chemical Transformations

Axially chiral phosphines are a class of extremely important ligands in asymmetric catalysis. Herein, an unprecedented copper（I）-catalyzed asymmetric SNAr reaction with HP（S）R2is uncovered, which delivers a series of axially chiral phosphine derivatives in high yields with excellent enantioselectivity. Furthermore, the diastereoselective reaction with the kinetic resolution of racemic HP（S）ArR proceeds smoothly, providing the products with moderate diastereoselectivity and excellent enantioselectivity. Control experiments indicate that HP（S）Ph2is much more active than HPPh2and HP（O）Ph2as the pronucleophile in the present reaction. It is found that the SNAr reaction （the first SNAr） proceeds in a desymmetric manner, providing the desired chiral products while a continued SNAr reaction （the second SNAr） slightly occurs in a kinetic resolution manner in the present catalytic system, which enhances the ee of the desired chiral products. DFTcalculations support a concerted reaction pathway rather than a step-wise mechanism. Finally, axially chiral olefin-phosphines produced by the present method work as suitable ligands in Pdcatalyzed asymmetric allylic substitution with C-, N-, and O-nucleophiles and Rh-catalyzed asymmetric addition of arylboronic acid to benzil.

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Adding new dimension to non-directed C（sp3）–H functionalizations

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Science China chemistry 2025年

作者： Konstantin P.Bryliakov Laboratory of Selective Oxidation Catalysis N.D.Zelinsky Institute of Organic Chemistry RAS

Aliphatic C–H groups are among the most abundant yet least reactive functional groups in organic molecules. Nature has evolved metalloenzymes such as those of the cytochrome P450 superfamily that efficiently activate individual tertiary（3） and secondary （2） C（sp3）–H bonds in complex molecules with the highest level of regio-and stereoselectivity [1], thus encouraging studies aimed at engineering artificial metalloenzymes for synthetic applications [2].

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Photoinduced radical sulfur dioxide insertion with asymmetric cyclization of alkenes: accessing β-chiral sulfones bearing S-stereocentric cyclic sulfinamides

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Science China chemistry 2025年第01期 257-263页

作者： Jiapian Huang Chenxin Wang Xu Wang Xiaoyu Zhou Wei Xiao Jie Wu School of Pharmaceutical and Chemical Engineering & institute for Advanced Studies Taizhou University State Key Laboratory of Organometallic chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences School of chemistry and Chemical Engineering Henan Normal University

The generation of various β-chiral sulfones bearing chiral cyclic sulfinamides through photoredox-catalyzed sulfur dioxide insertion with asymmetric radical cyclization is described. This method features a broad substrate scope and excellent stereospecificity. Computational studies reveal that the dispersion interaction between sulfinyl group and CH2SO2Ph group plays a crucial role in the stereoselectivity control.

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Photosynthetic reaction pathways of natural and artificial systems

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Science China chemistry 2025年

作者： Shixing Lei Liting Bi Lingxuan Chen Zhanting Li Jia Tian State Key Laboratory of Organometallic chemistry and Shanghai Hong Kong Joint Laboratory in Chemical Synthesis Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences

Photosynthesis converts solar energy into chemical energy through highly coordinated photosynthetic *** by natural systems,artificial photosynthesis aims to develop an efficient,sustainable,and cost-effective pathway for solar-tochemical *** review examines natural photosynthetic pathways,including retinal/rhodopsin-,bacteriochlorophyll-,and chlorophyll-based systems,highlighting their key components and ***,we outline reaction pathways in artificial photosynthetic systems constructed via heterogeneous,homogeneous,self-assembly,and semi-artificial strategies,focusing on water splitting,carbon fixation,and nitrogen ***,we offer insights into future directions for artificial photosynthesis,emphasizing the importance of using self-assembly strategies and the potential of using primitive phototrophic microorganisms as models.

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Synthesis and Crystal Structure of 2-Amino-4- chloro-5-(4-methylbenzyl)-6-methylpyrimidine

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Chinese Journal of Structural chemistry 2007年第9期26卷 1005-1008页

作者：郭万成刘幸海陈沛全宋海滨李正名 elemento-organic chemistry institute State Key Laboratory of Elemento-organic Chemistry Nankai University

The title compound 2-amino-4-chloro-5-（4-methylbenzyl）-6-methylpyrimidine （C26H28Cl2N6, Mr = 495.44） has been synthesized and its crystal structure was determined by single-crystal X-ray diffraction analysis. The crystal belongs to monoclinic, space group P21/c with a = 14.892（7）, b = 6.129（3）, c = 14.889（7）A, β = 109.795（8）°, V = 1278.7（10）A^ 3, Z = 2, F（000） = 520, Dc = 1.287 g/cm^3, μ = 0.280 mm^-1, the final R = 0.0577 and wR = 0.1589 for 1357 observed reflections with I 〉 2σ（I）. A total of 6091 reflections were collected, of which 2257 were independent （Rint = 0.033）. The X-ray analysis reveals that the chlorine atom and methyl of the title compound are disordered.

关键词： synthesis crystal structure X-ray diffraction

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Synthesis and Crystal Structure of Diethyl 5-Acetoxy-3-(4-chlorophenyl)- 4,5-dihydroisoxazol-5-yl-5-phosphonate

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Chinese Journal of Structural chemistry 2006年第12期25卷 1453-1456页

作者：尚志强陈茹玉黄有 State Key Laboratory of elemento-organic chemistry Institute of Elemento-organic Chemistry Nankai University

The crystal structure of the title compound, diethyl 5-acetoxy-3-（4-chlorophenyl）-4,5- dihydroisoxazol-5-yl-5-phosphonate （C15H19CINO6P, Mr = 375.73）, has been synthesized by the treatment of nitrile oxides and l-acetyloxy-vinylphosphonate under very mild conditions in good yields, and determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group C2/c with a = 16.914（10）, b = 10.567（7）, c = 21.927（13） A, β = 110.249（11）°, V = 3677（4） A^3, Z = 8, Dc = 1.358 g/cm^3, F（000） = 1568,/l（MoKa） = 0.324 mm^-1）, S = 1.011, the final R = 0.0661 and wR = 0.1556. The X-ray analytic results showed that the dihedral angle between the phenyl group and the isoxazoline ring is 10.7°.

关键词： crystal structure isoxazolines phosphonate synthesis

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Enantioselective β-alkenylation of α,β-unsaturated aldehydes via chiral biphosphine ligand modified dirhodium(II) catalysis

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Science China chemistry 2025年

作者： Guangli Xu Hongda Chen Xiaoming Wang State Key Laboratory of Organometallic chemistry and Shanghai Hongkong Joint Laboratory in Chemical Synthesis Center for Excellence in Molecular Synthesis Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences School of chemistry and Materials Science Hangzhou Institute for Advanced Study University of Chinese Academy of Sciences School of chemistry and Chemical Engineering Henan Normal University

Dirhodium(II) complexes have achieved great success in organic synthesis,and fine-tuning their catalytic properties with various bridging ligands is well-investigated in carbene ***,combining dirhodium(II) with a sophisticated ligand as a catalyst in other reactions is still extremely challenging,especially for the asymmetric synthesis of valuable chiral ***,we report a dirhodium(II)/(S)-MeO-BIPHEP catalytic system for the challenging asymmetric β-alkenylation of α,β-unsaturated aldehydes,affording the corresponding chiral conjugate addition products in good yields with high enantioselectivities.A couple of drug-derived substrates were also compatible with the protocol,which has been successfully used to prepare biologically relevant pyranochromene *** mechanistic studies suggested that the dirhodium core might remain intact over the catalytic cycle,and the chiral diphosphine ligand plays a key role in this novel reactivity and determining the high enantioselectivities of the asymmetric conjugate addition.

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Boosting hydrocarbon conversion via Cu-doping induced oxygen vacancies on CeO2 in CO2 electroreduction

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Journal of Energy chemistry 2025年第1期100卷 66-76页

作者： Lei Xue Tong Shi Chenhui Han Heng Zhang Fenrong Liu Haorun Li Yan Wang Xiaojun Gu Shanghong Zeng Inner Mongolia Key Laboratory of chemistry and Physics of Rare Earth Materials School of Chemistry and Chemical Engineering Inner Mongolia University State Key Laboratory of Coal Conversion Institute of Coal Chemistry Chinese Academy of Sciences institute of Catalysis Department of Chemistry Zhejiang University National Key Laboratory of Baiyunobo Rare Earth Resource Research and Comprehensive Utilization Baotou Research Institute of Rare Earths

Conversion of CO2back to hydrocarbons is the most direct way of closing the“carbon cycle”,and its significance is further enlarged if this process is driven by renewable energies such as ***,precisely controlling the product selectivity towards hydrocarbons against the competitive hydrogen evolution remains challenging,especially for Cu-based ***,we report a novel defect engineering strategy,by which Cu-doping-induced oxygen vacancies on CeO2nanorods were effectively created,with adjustable vacancy/Cu *** resulting optimum catalyst shows up to 79% catalytic current density to hydrocarbons （excluding CO）,with 49% faradaic efficiency to *** and density functional theory unveil that the ratio between oxygen vacancy and Cu affects significantly the formation of*CHO and activation of H2O,which leads to the following deep hydrogenation to *** findings may spur new insights for designing and developing more controllable chemical process relevant to CO2utilization.

关键词： Nanorods

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Synthesis and Crystal Structure of 1,2-Bis(1-phenyl-3-methylthio- 4-iminopyrazolo[3,4-d]pyrimidin-5-yl) ethane

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Chinese Journal of Structural chemistry 2002年第2期21卷 136-138页

作者：陈卫强金桂玉等 institute of elemento-organic chemistry Nankai University State Key Laboratory of Elemento-organic Chemistry 天津 300071

The title compound 1,2-bis(1-phenyl-3-methylthio-4-iminopyrazolo[3,4-d] pyrimidin-5-yl)ethane (C26H24N10S2, Mr = 540.67) was obtained by the reaction of (1-phenyl-4- cyano)pyrazol-5-yliminomethyl ethyl ether with ethyldiamine. The crystal is monoclinic, space group P21/c with a = 10.460(2), b = 8.004(2), c =15.434(3) ? b = 90.803(3)? V = 1292.1(4) 3, Z = 2, Dc = 1.390 g/cm3, F(000) = 564, m(MoKa) = 0.24 mm-1, R = 0.0560 and wR = 0.1344 for 2286 observed reflections (I > 2s (I)). In this compound the dihedral angle between the plane defined by C(2), N(1), N(2), C(3), C(6), N(3), C(4), N(4), C(5) and N(5) atoms and the phenyl ring is 34.78? The six-membered ring consisted of C(3), N(3), C(4), N(4), C(5) and C(6) atoms forms a p67 configuration in which the N(4) atom is sp2 hybrid. There exist weak hydrogen bonds between S(1) and N(5) atoms (NHS, 3.430 ?.

关键词： crystal structure pyrazolo[3,4-d]pyrimidine purine analogs Ethyl N-pyra- zolyformimidate synthesis

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Synthesis and Crystal Structure of N-[1-(4-Chlorophenyl)-1,4-dihydro-4-oxe-6-methylpyridazine-3-carbonyl]-N'-benzoylhydrazine

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Chinese Journal of Structural chemistry 2001年第3期20卷 191-194页

作者：邹霞娟翁林红金桂玉王宏根 institute of elemento-organic chemistry State Key Laboratory of Elemento-Organic ChemistryNankai University Tianjin 300071 China

The title compound N-[1-(4-chlorophenyl)-1,4-dihydro-4-oxe-6-methylpyridazine- 3-carbonyl]-N(-benzoylhydrazine was prepared by the reaction of 1-(4-chlorophenyl)-1,4- dihydro-4-oxe-6-methylpyridazine-3-carboxylic acid with chloroformate ethyl ester and benzoyl hydrazine in the presence of triethylamine. The crystal structure ([C19H15ClN4O3]2·C2H5OH, Mr =811.67) has been determined by X-ray crystal structural analysis. The crystal is monoclinic, space group P21/c, with unit cell parameters a=13.296(3), b=17.155(3), c=17.459(3)?,β=98.959(4), Z=4, V=3934(1) ?3, Dc=1.371g/cm3, F(000)=1688, μ(MoKα)=0.226 mm-1, R=0.0495, wR=0.1348 for 3345 observed reflections (I >2σ(I)). The hydrogen bonds N(3)－H…O(1) , N(7)－H…O(4), and N(8)－H…O(2) can be observed.

关键词： acylhydrazinocabonylpyridazinone crystal structure synthesis

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