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Enantioselective reductive conjugate alkenylation of α,β-enones with keto alkenyl acetates by nickel catalysis

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Science China Chemistry 2025年第1期68卷 157-162页

作者： Rong-De He Yun-Lei Luo Qiu-Quan Pan Qi-Wei Yao Xing-Zhong Shu State Key laboratory of Applied organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University

Reactions involving alkenyl acetates offer cost-effective and environmentally friendly routes for alkene synthesis, yet their asymmetric variant remains elusive. Concurrently, asymmetric conjugate alkenylation predominantly centered on nucleophilic addition using alkenyl–M. This manuscript presents an asymmetric reductive conjugate alkenylation reaction involving alkenyl acetates. The method facilitates the enantioselective addition of keto alkenyl groups to α,β-enones, resulting in the formation of unsaturated diketones—a class of useful structural motifs that are challenging to access otherwise. The use of electron-rich Pyroxy ligand is essential for achieving both high reaction efficiency and enantioselectivity.

关键词： nickel alkenylation asymmetric cross-coupling alkenes

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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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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Emerging progress: photochemical transformation of nitroso compounds

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Science China Chemistry 2025年第1期68卷 118-133页

作者： Ze-Le Chen Qiang-Qiang Li Armido Studer Jun Xuan Anhui Province Key laboratory of Chemistry for Inorganic/organic Hybrid Functionalized Materials School of Chemistry & Chemical Engineering Anhui University Organisch-Chemisches Institut Universitat Münster

Nitroso compounds have emerged as highly valuable reaction partners or reagents in organic synthesis due to their rich *** versatile profile of these compounds allows them to function as electrophiles, nucleophiles, diradicals, and radical acceptors in diverse transformations. In recent years, notable progress has been made in harnessing photochemical reactions with nitroso compounds to prepare N,O-containing structures using mild and eco-friendly conditions. Various nitroso compounds like nitrosoarenes, acyloxy nitroso compounds, N-nitrosoamines and nitrites have received significant attention for their ability to introduce NO moieties into complex molecules that are otherwise difficult to access. In this review, we provide an overview of the recent advancements in the visible light-induced conversion of nitroso compounds, with particular emphasis on their role as bifunctional reagents and acceptors of radicals, carbenes and nitrenes.

关键词： nitroso compounds photochemistry radical reaction carbene transformation nitrosoarenes

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

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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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Nitrogen addition promotes soil carbon accumulation globally

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Science China Life Sciences 2025年第1期68卷 284-293页

作者： Xuemei Yang Suhui Ma Erhan Huang Danhua Zhang Guoping Chen Jiangling Zhu Chengjun Ji Biao Zhu Lingli Liu Jingyun Fang Institute of Ecology College of Urban and Environmental Sciencesand Key Laboratory for Earth Surface Processes of the Ministry of EducationPeking University Ministry of Education Key laboratory for Transboundary Ecosecurity of Southwest China School of Ecology and Environmental ScienceYunnan University State Key laboratory of Vegetation and Environmental Change Institute of BotanyChinese Academy of Sciences

Soil is the largest carbon(C) reservoir in terrestrial ecosystems and plays a crucial role in regulating the global C cycle and climate *** nitrogen(N) deposition has been widely considered as a critical factor affecting soil organic carbon(SOC) storage, but its effect on SOC components with different stability remains unclear. Here, we analyzed extensive empirical data from 304 sites worldwide to investigate how SOC and its components respond to N addition. Our analysis showed that N addition led to a significant increase in bulk SOC(6.7%), with greater increases in croplands(10.6%) and forests(6.0%) compared to grasslands(2.1%). Regarding SOC components, N addition promoted the accumulation of plant-derived C(9.7%–28.5%) over microbial-derived C(0.2%), as well as labile(5.7%) over recalcitrant components(–1.2%), resulting in a shift towards increased accumulation of plant-derived labile C. Consistently, N addition led to a greater increase in particulate organic C(11.9%) than mineral-associated organic C(3.6%), suggesting that N addition promotes C accumulation across all pools, with more increase in unstable than stable pools. The responses of SOC and its components were best predicted by the N addition rate and net primary productivity. Overall, our findings suggest that N enrichment could promote the accumulation of plant-derived and non-mineral associated C and a subsequent decrease in the overall stability of soil C pool, which underscores the importance of considering the effects of N enrichment on SOC components for a better understanding of C dynamics in soils.

关键词： meta-analysis nitrogen enrichment soil organic carbon carbon accumulation carbon stability

Dative B–N bonds weaven toward two-dimensional purely organic materials for single crystals

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Science China Chemistry 2025年第1期68卷 12-14页

作者： Wei-Lei Zhou Siwei Wang Yong Chen College of Chemistry and Materials Science Inner Mongolia Key Laboratory of Chemistry for Nature Products and Synthesis for Functional Molecules Innovation Team of Optical Functional Molecular Devices Inner Mongolia Minzu University College of Chemistry Nankai University

Molecular topology is one of the important topics to study and understand the relationship between molecular structure and properties [1]. Particularly, two-dimensional (2D) materials with extremely high surface area and ultra-thin morphology have attracted considerable attention due to their unexpected properties in materials and chemistry [2,3].

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De novo synthesis of atropisomeric benzofurans via Cu/SPDO complex catalyzed asymmetric formal [3 + 2] annulation

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Science China Chemistry 2025年第1期68卷 174-180页

作者： Fan-Xiao Meng Xing-Yu Wang Ka Lu Ju-Song Yang Fu-Min Zhang Ai-Jun Ma Bao Du Yong-Qiang Tu State Key laboratory of Applied organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University School of Chemistry and Chemical Engineering Shanghai Jiao Tong University School of Biotechnology and Health Sciences Wuyi University

Herein, the de novo synthesis of atropisomeric benzofurans through the Cu/spirocyclic-pyrrolidine-oxazoline(SPDO) complex catalyze asymmetric formal [3 + 2] cycloaddition between quinones and ynamides is explored, producing a range of structurally diverse axially chiral benzofurans in satisfactory yields with good to excellent enantioselectivities. Furthermore, density functional theory calculations were applied to explain the possible reaction mechanism.

关键词： benzofuran atropisomers novel de novo synthetic strategy asymmetric formal [3 + 2] cycladdition Cu/SPDO complex DFT calculations

Unraveling the impacts of intermolecular interaction on morphology evolution for highly efficient organic solar cells and modules

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Science China Chemistry 2025年第1期68卷 264-272页

作者： Xueqing Ma Yingying Cheng Yuqiang Liu Xinming Zheng Guangliu Ran Hongxiang Li Xinyue Cui Andong Zhang Wenkai Zhang Pei Cheng Wenchao Huang Zhishan Bo Beijing Key laboratory of Energy Conversion and Storage Materials College of Chemistry Beijing Normal University College of Textiles and Clothing State Key Laboratory of Bio-fibers and Eco-textiles Qingdao University Key State laboratory of Advanced Technology for Materials synthesis and Processing School of Materials Science and EngineeringWuhan University of Technology Department of Physics and Applied Optics Beijing Area Major laboratory Center for Advanced Quantum Studies Beijing Normal University State Key laboratory of Polymer Materials Engineering College of Polymer Science and Engineering Sichuan University

Understanding the effect of intermolecular interaction on the growth dynamic of active layers is critical for advancing organic solar cells(OSCs). However, the diverse structure of donors and acceptors makes the research challenging. Additives with customizable structures and properties could simplify this complexity. Herein, we meticulously tailor two additives of 3,4-ethylenedioxythiophene(EDOT) and 2,5-dibromo-3,4-ethylenedioxythiophene(DBEDOT), possessing distinct intermolecular interaction features to elaborate the inherent relationship. It is found that varied interaction strengths can alter film formation processes. The enhanced intermolecular interaction between the DBEDOT and non-fullerene acceptor BTP-e C9-4F results in pre-aggregation and longer crystallization duration of BTP-e C9-4F, facilitating the formation of films with compact molecular packing and decent phase separation. Thus, exciton dissociation and charge transport become more efficient. Finally, devices processed with DBEDOT exhibit a remarkable power conversion efficiency of 19.35% in small-area OSCs and 14.11% in bladecoated 5 cm × 5 cm organic solar mini-modules. Especially, OSCs can maintain 80% of their initial efficiency after continuous annealing at 85 °C for over 2,100 h.

关键词： organic solar cell non-fullerene acceptor film growth molecular packing intermolecular interaction