Article
Chemistry, Organic
Eric M. Miller, Maciej A. Walczak
Summary: This study presents stereoselective C-arylation and etherification reactions of anomeric trifluoroborates derived from BMIDA esters, exhibiting high anomeric selectivities for 2-deoxysugars and showing a broad substrate scope, including disaccharides and trifluoroborates with free hydroxyl groups. This new class of carbohydrate reagents adds to the palette of anomeric nucleophile reagents suitable for efficient installation of C-C bonds.
Article
Chemistry, Organic
Pan Zhou, Xinxuan Li, Dong Wang, Tao Xu
Summary: The dual nickel/photoredox-catalyzed enantioselective reductive cross-coupling of aryl halides with CF3-substituted racemic alkyl electrophiles has been developed, allowing access to a variety of chiral CF3-containing compounds. The mild conditions and absence of Grignard reagents or stoichiometric metallic reductants make this transformation highly potential for late-stage functionalization of complex molecules.
Article
Chemistry, Physical
Ziyin Kong, Weipeng Hu, James P. P. Morken
Summary: A Pt-catalyzed hydrosilylation reaction of (Z)-1,2-diborylethylene leads to the formation of a 1,2-diboryl-1-silylalkane, which can be used in catalytic cross-coupling reactions. Depending on the catalyst and the reaction conditions, the coupling can occur at either the α or β position relative to the silane center.
Article
Chemistry, Organic
Anthony N. Cauley, Antonio Ramirez, Chandan L. Barhate, Andrew F. Donnell, Purnima Khandelwal, Melda Sezen-Edmonds, Trevor C. Sherwood, Jack L. Sloane, Cullen L. Cavallaro, Eric M. Simmons
Summary: By utilizing quinoline as a mild catalytic additive, a broadly applicable method for Ni/photoredox-catalyzed C(sp(2))-C(sp(3)) cross-coupling was developed, which can be used in both batch and flow reactions. The method is effective for both primary benzylic nucleophiles and stabilized/nonstabilized secondary alkyl boronic esters.
Article
Chemistry, Organic
Anton A. Gladkov, Grigory N. Chernov, Vitalij V. Levin, Vladimir A. Kokorekin, Alexander D. Dilman
Summary: Organozinc reagents can generate alkyl radicals under blue light irradiation with an organic photocatalyst, leading to gem-difluorinated products by trapping the radicals with alpha-(trifluoromethyl)styrenes and eliminating fluoride. The reaction can be conveniently carried out under Barbier conditions starting from organic iodides and bromides and elemental zinc.
Article
Chemistry, Organic
Yueyue Ma, Jufei Hong, Xiantong Yao, Chengyu Liu, Ling Zhang, Youtian Fu, Maolin Sun, Ruihua Cheng, Zhong Li, Jinxing Ye
Summary: This method utilizes electrolysis processes, eliminating the need for a terminal oxidant, sacrificial anode, metal reductant, and prefunctionalized radical precursor. It shows broad functional group tolerance and provides a more environmentally friendly and synthetically practical approach for forming C(sp2)-C(sp3) bonds.
Review
Chemistry, Multidisciplinary
Suparna Mondal, Kanak Kanti Das, Santanu Panda
Summary: Transition metal-catalyzed cross-coupling reactions have had a significant impact on chemical synthesis. Among these, iron catalysis has attracted attention due to its cost effectiveness, stable oxidation states, Lewis acidity, and relatively low toxicity. This review summarizes the development of iron-catalyzed C-C bond forming reactions over the past two decades, highlighting the challenges encountered in the past decade.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Hepan Wang, Purui Zheng, Xiaoqiang Wu, Yuqiang Li, Tao Xu
Summary: In this study, a general synthetic method for chiral alpha-aryl phosphorus compounds was reported, which involves a dual catalytic system to achieve enantioconvergent reductive cross-coupling between alpha-bromophosphates and aryl iodides. The method exhibited high efficiency and can accommodate substrates with diverse functional groups.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Yael Ben-Tal, Guy C. Lloyd-Jones
Summary: The Ni/Ir-photocatalyzed coupling of ArBr with RBr was studied using in situ LED -F-19 NMR spectroscopy. Factors such as light, ArBr, Ni, and Ir were found to control the rate of ArBr consumption, while [(TMS)3SiH] and RBr independently controlled the product selectivity. The major resting state of nickel was identified as ArNiII(L)Br, and the complex undergoes Ir-photocatalyzed conversion to products in competition with the release of ArBr.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Saidkhodzha Nematulloev, Arunachalam Sagadevan, Badriah Alamer, Aleksander Shkurenko, Renwu Huang, Jun Yin, Chunwei Dong, Peng Yuan, Khursand E. Yorov, Azimet A. Karluk, Wasim J. Mir, Bashir E. Hasanov, Mohamed Nejib Hedhili, Naveen M. Halappa, Mohamed Eddaoudi, Omar F. Mohammed, Magnus Rueping, Osman M. Bakr
Summary: This study reports the synthesis of atomically precise copper hydride nanoclusters with a controlled defect, which were demonstrated to be highly selective catalysts for C-C cross-couplings. The work highlights the potential of defective nanoclusters as model systems for investigating individual defects, correlating defects with physicochemical properties, and rationally designing new nanoparticle catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Inorganic & Nuclear
Angelita M. Barcellos, Manoela Sacramento, Gabriel P. da Costa, Gelson Perin, Eder Joao Lenardao, Diego Alves
Summary: Organochalcogen compounds have significant synthetic and biological applications. The coupling reaction between boronic acids, borate anions or boronic esters with different sources of chalcogen mediated by transition metals is a powerful tool for the formation of functionalized diorganyl chalcogenides. This strategy allows for the preparation of selenides, sulfides, and tellurides with high complexity and molecular diversity in good to excellent yields.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Ayan Jati, Suranjana Dam, Shekhar Kumar, Kundan Kumar, Biplab Maji
Summary: Researchers synthesized a pyrene-based two-dimensional C=C linked pi-conjugated COF with Ni(ii)-centers through bipyridine moieties. This COF catalyst exhibited significantly higher efficiencies in diverse photocatalytic C-X cross-coupling reactions compared to homogeneous controls, due to enhanced energy and electron transfer.
Article
Chemistry, Multidisciplinary
Jacob W. Greenwood, Benjamin T. Boyle, Andrew McNally
Summary: Radical couplings of cyanopyridine radical anions offer a valuable technology for functionalizing pyridines in pharmaceuticals, agrochemicals, and materials. This study demonstrates that pyridylphosphonium salts can be useful alternatives to cyanopyridines in radical-radical coupling reactions, expanding the scope of complex pyridines. Additionally, late-stage functionalization of pharmaceuticals is highlighted as an advantage of pyridylphosphonium salts over cyanopyridines.
Article
Chemistry, Physical
Hyesung Lee, Choah Kwon, Sekar Vikneshvaran, Sukjun Lee, Sang-Yup Lee
Summary: In this study, a single-atom Cu catalyst supported on amorphous carbon was prepared for direct methane partial oxidation. Carbonization of Cu-doped ZIF-8 resulted in the implantation of single-atom Cu active centers on the amorphous N-doped carbon. The prepared catalyst exhibited high selectivity and stability for methane oxidation.
APPLIED SURFACE SCIENCE
(2023)
Article
Nanoscience & Nanotechnology
Chen Yang, Lei Zhang, Chenxi Lu, Shuyao Zhou, Xingxing Li, Yanwei Li, Yang Yang, Yu Li, Zhirong Liu, Jinlong Yang, K. N. Houk, Fanyang Mo, Xuefeng Guo
Summary: Conventional analytic techniques provide valuable insights on reaction mechanisms, but single-molecule junctions offer real-time detection of molecular processes, particularly in Suzuki-Miyaura coupling reactions. Integrating a single-molecule Pd catalyst into graphene junctions enables electrical monitoring of the complete catalytic cycle and resolves controversial mechanisms.
NATURE NANOTECHNOLOGY
(2021)
Article
Chemistry, Organic
Ding Ding, Liang Xu, Yu Wei
Summary: An unprecedented electrochemical approach for the synthesis of alpha-keto acetals has been developed, which combines electrochemistry and organoselenium catalysis. The desired products are obtained at room temperature without the need for basic or metallic additives, allowing for simultaneous incorporation of carbonyl and acetal motifs across the triple bonds in a single step.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yuan Zhu, Weisai Zu, Qing Tian, Zifeng Cao, Yu Wei, Liang Xu
Summary: In this study, a collaborative approach using AQDAB as an organoboron photocatalyst and nickel catalyst in metallaphotoredox catalyzed reactions has been developed to achieve efficient C(sp(2))-P and C(sp(2))-S cross-coupling. The strategy enables the coupling of aryl halides with diarylphosphine oxides and thiols at room temperature under an air atmosphere, leading to the synthesis of triarylphosphine oxides and thioethers in generally moderate to good yields.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Zhengwei Ding, Zhi Liu, Zhijun Wang, Tao Yu, Ming Xu, Jingru Wen, Kaiyan Yang, Hailong Zhang, Liang Xu, Pengfei Li
Summary: This study reports an economical reaction using commercial diboron(4) as a catalyst. By designing a catalytic cycle and using a pyridine cocatalyst, boronyl radicals can be generated and transferred reversibly. The reaction features metal-free conditions, inexpensive and stable catalysts, simple operation, and a broad substrate scope compared to transition metal-based catalysts.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Xiaoman Li, Jiawei Huang, Liang Xu, Ping Liu, Yu Wei
Summary: In this study, a tetrabutylammonium tribromide-mediated three-component reaction of alkenes, diselenides, and sulfoximines was established, providing a direct and metal-free access to diverse beta-arylseleno sulfoximine derivatives. This regioselective sulfoximido-selenization protocol proceeds efficiently under mild and ambient conditions with generally good yields. The strategy is characterized by step and atom economy, practicability, a broad substrate scope, and gram-scale synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yuan Gao, Zhijun Wang, Xinyu Zhang, Min Zhao, Shuai Zhang, Chao Wang, Liang Xu, Pengfei Li
Summary: In this study, novel chiral half-sandwich iridium catalysts were designed and synthesized, which enabled the preparation of a broad range of α-chiral (hetero)aryl amines with high yield and enantioselectivity. The optimized catalyst and azeotropic mixture of formic acid and triethylamine were used as the hydrogen source under mild and operationally simple conditions. This work introduced an effective chiral catalyst for the simplified synthesis of medicinally important chiral amines, and also provided a rare example of robust enantioselective transition-metal catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jiawei Huang, Xiaoman Li, Liang Xu, Yu Wei
Summary: A three-component oxychalcogenation reaction is achieved in this study, using alkenes, diselenides/thiophenols, and H2O/alcohols as reactants. Tetrabutylammonium tribromide (TBATB) and dimethylsulfoxide (DMSO) are employed as the catalyst and terminal oxidant, respectively, enabling the difunctionalization transformation. This metal-free reaction system shows excellent functional group compatibility and provides a unified and practical approach to access beta-hydroxyl or beta-alkoxy organochalcogenides.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Tao Yu, Jinbo Yang, Zhijun Wang, Zhengwei Ding, Ming Xu, Jingru Wen, Liang Xu, Pengfei Li
Summary: In this study, a novel [2 sigma + 2 sigma] radical cycloaddition reaction between bicyclo[1.1.0]butanes (BCBs) and cyclopropyl ketones was developed. This reaction provides a modular, concise, and atom-economical synthetic route to substituted bicyclo[3.1.1]heptane (BCH) derivatives, which are 3D bioisosteres of benzenes and core skeleton of terpene natural products. The reaction was catalyzed by a combination of tetraalkoxydiboron(4) compound B(2)pin(2) and 3-pentyl isonicotinate. The broad substrate scope was demonstrated by synthesizing highly functionalized BCHs with up to six substituents on the core and up to 99% isolated yield. Computational mechanistic investigations supported a pyridine-assisted boronyl radical catalytic cycle.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Biochemistry & Molecular Biology
Jinbo Yang, Xiangxue Cao, Lanfeng Wei, Jianshu Zhang, Jinli Zhang, Ping Liu, Liang Xu, Pengfei Li
Summary: In this study, a four-coordinated organoboron compound, aminoquinoline diarylboron (AQDAB) was used as a photocatalyst for the oxidation of silane to silanol. This method efficiently oxidizes Si-H bonds to form Si-O bonds. The corresponding silanols can be obtained in moderate to good yields at room temperature under oxygen atmospheres, providing a green protocol for the preparation of silanols.
Article
Chemistry, Organic
Changpeng Chen, Zhijun Wang, Sha Wang, Liang Xu, Xiaoming Zeng
Summary: We describe the selective cyclization of anilines with cyclobutanones and congeners using chromium catalysis. This reaction enables the formation of diastereoselective tetrahydroquinolines by linking two strained four-membered rings, leading to the synthesis of cyclobutane-fused and constrained spirotetrahydroquinolines (STHQs) and complex multiple spiro carbon-containing polyazacycles. The constrained STHQs have been utilized as versatile precursors for the synthesis of oxygen-, nitrogen-, and thio-substituted spiro analogues, as well as dioxygen-incorporated spiroazacycles.
Letter
Chemistry, Organic
Panchi Guo, Hao Jin, Jinhui Han, Liang Xu, Pengfei Li, Miao Zhan
Summary: This study demonstrates a nickel-catalyzed Negishi cross-coupling reaction for the synthesis of versatile organoboron products with high functional-group tolerance. The reaction allows for the coupling of unactivated tertiary alkyl electrophiles with boron-stabilized organozinc reagents. The importance of the Bpin group in accessing the quaternary carbon center is highlighted, and the practicality of the prepared quaternary organoboronates is showcased through their conversion to other useful compounds.
Article
Chemistry, Multidisciplinary
Jiawei Huang, Xiaoman Li, Yu Wei, Zhigang Lei, Liang Xu
Summary: A novel photoredox process using AQDAB and TBAI as co-catalysts has been developed for N-functionalization of NH-sulfoximines/sulfonimidamides. The protocol offers good to excellent yields of N-sulfenylated and N-phosphonylated products without the need for metallic (photo)catalysts, external oxidants, or acidic/basic additives. This method is tolerant to a wide range of functional groups and allows the N-phosphonylation of NH-sulfonimidamides for the first time.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Lanfeng Wei, Wenbo Bai, Zhiyan Hu, Zhiyong Yang, Liang Xu
Summary: The study developed a unified metal-free photooxidative platform for the cleavage of C-heteroatom bonds, using AQDAB complex as the photocatalyst to induce the oxidation process. This method allows for chemoselective cleavage of C-N, C-S, and C-Se bonds, broadening the potential applications of oxidation in synthetic chemistry. It established a photooxidation system for formal carbonylation of C-heteroatom (N, S, Se) bonds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Yuge Li, Liang Xu, Yu Wei
Summary: This study established copper-catalyzed tandem cyclization reactions between arylboronic acids and anthranils, providing a new approach for one-pot assembly of azacycle acridines. The protocol features simple operation, precious-metal-free conditions, and good functional group compatibility, offering an efficient method for synthesizing a variety of acridines in moderate to good yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jing Wang, Zenghui Li, Gaoqiang You, Liang Xu, Pin Gao, Bin Rao
Summary: In this study, phosphorylated benzyne precursors were efficiently synthesized and used in a series of versatile reactions to achieve the synthesis of poly-substituted organophosphorus arenes with high regioselectivity at the C1 position of the benzynes.
NEW JOURNAL OF CHEMISTRY
(2022)