Article
Chemistry, Organic
Hui-Qing Geng, Wenbo Li, Yanying Zhao, Xiao-Feng Wu
Summary: In this communication, a new strategy for the synthesis of diborylated cyclopropanes via a copper-catalyzed carbonylation process was introduced. The strategy showed high yields and complete diastereoselectivity. The obtained products were further transformed to demonstrate their utility in organic synthesis.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Yang Yuan, Nai-Xian Sun, Chang-Sheng Wang, Kai Guo, Xiao-Feng Wu
Summary: We have developed an efficient method for synthesizing one-carbon-extended alcohols through cobalt-catalyzed hydroxymethylation of alkyl halides using carbon monoxide as the C1 source and cost-effective and environmentally friendly PMHS as the hydride source. This method includes a ligand-free cobalt catalyst and exhibits broad functional group tolerance.
Article
Chemistry, Multidisciplinary
Fu-Peng Wu, Hui-Qing Geng, Xiao-Feng Wu
Summary: A copper-catalyzed boroaminomethylation of olefins with CO as the C1 source via the mechanism of a carbene insertion into the N-H bond is reported in this study. This method affords valuable gamma-boryl amines from four inexpensive readily available chemicals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Fu-Peng Wu, Xiao-Feng Wu
Summary: This study reports a borylative methylation reaction catalyzed by CuH and CuBpin, yielding moderate to good yields of alkyl boranes. In this cooperative system, CuH reacts with alkyl iodide faster than CuBpin.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Maruti Mali, Gangavaram V. M. Sharma, Subhash Ghosh, Thierry Roisnel, Bertrand Carboni, Fabienne Berree
Summary: A Simmons-Smith stereodefined procedure for the synthesis of cyclopropyl-1,2-bis(boronates) starting from alkenes has been developed. The resulting compounds were then subjected to regioselective Suzuki-Miyaura couplings to produce diversely substituted arylcyclopropanes in good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shuailong Li, Dequan Zhang, Runtong Zhang, Shao-Tao Bai, Xumu Zhang
Summary: This article reports a novel rhodium catalyst that enables highly efficient and selective hydroformylation of cyclopropyl-functionalized trisubstituted alkenes, resulting in valuable chiral cyclopropyl entities. The modified ligand used in this study exhibits superior performance compared to traditional diphosphine ligands in asymmetric catalysis. Gram-scale reactions and subsequent transformations of the products were also demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Ninglin Li, Fuqiang Xiong, Ke Gao
Summary: An efficient cobalt-based catalytic system has been developed for the protodeboronation of various aryl and vinyl boronates, tolerating a wide range of functional groups. Additionally, the reaction has been extended to deuterodeboronation with D2O, offering a potential protocol for the synthesis of regiospecifically deuterated arenes and olefins.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Mahesh M. Parsutkar, Subhajit Bhunia, Mayukh Majumder, Remy F. Lalisse, Christopher M. Hadad, T. V. RajanBabu
Summary: The synthesis of enantiopure homoallylic boronate esters via cobalt-catalyzed [4,3]hydroboration of 1,3-dienes is described. Chiral bis-phosphine ligands with a narrow bite angle have been identified as efficient catalysts for achieving high enantioselectivities. Additionally, a dibenzooxaphosphole ligand is found to provide excellent regioselectivities and enantioselectivities for a broad range of substrates.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Yuehua Zeng, Yajun Li, Daqi Lv, Hongli Bao
Summary: A novel copper-catalyzed, three-component reaction has been developed for the direct oxycyanation of various alkenes using aryl diacyl peroxides and trimethylsilyl cyanide. Both unactivated alkenes and styrenes serve as reliable substrates and yield beta-cyanohydrin derivatives. An asymmetric version of this reaction has also been successfully conducted.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Mahadev L. Shegavi, Suresh Saini, Ramesh Bhawar, Meghana Desai Vishwantha, Shubhankar Kumar Bose
Summary: This study reports the anti-Markovnikov-selective hydroboration of alkenes catalyzed by Fe-dopamine-Cu NPs, as well as their application in the beta-borylation of alpha,beta-unsaturated ketones and esters, achieving high yields of alkylboronate esters. Furthermore, the magnetically recyclable catalyst maintained high activity over multiple reaction runs.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Ming Chen
Summary: A new synthetic method for coupling vinylidene cyclopropanes with allyl or allenyl boronates using a copper catalyst is reported. This reaction forms a C-C bond at the terminal carbon atom of the allene moiety of vinylidene cyclopropanes and opens the cyclopropane ring simultaneously. Moreover, the resulting copper-enolate intermediate can be intercepted by external electrophiles.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Yang Yuan, Youcan Zhang, Wenbo Li, Yanying Zhao, Xiao-Feng Wu
Summary: A novel method for constructing amide bonds through anti-Markovnikov hydroaminocarbonylation of unactivated alkenes has been developed. Copper catalysis, hydroxylamine electrophile reagents, and poly(methylhydrosiloxane) (PMHS) were used under mild conditions. The reaction showed a high degree of tolerance towards various functional groups and efficiently converted unactivated terminal alkenes, 1,1-disubstituted alkenes, and cyclic alkenes to the corresponding amides with exclusive anti-Markovnikov selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yang Yuan, Youcan Zhang, Wenbo Li, Yanying Zhao, Xiao-Feng Wu
Summary: This paper reports a general method for the anti-Markovnikov hydroaminocarbonylation of unactivated alkenes under mild conditions, using copper catalysis in combination with hydroxylamine electrophile reagents and poly(methylhydrosiloxane) (PMHS) as a cheap and environmentally friendly hydride source. The reaction tolerates a variety of functional groups and efficiently converts unactivated terminal alkenes, 1,1-disubstituted alkenes, and cyclic alkenes to the corresponding amides with exclusive anti-Markovnikov selectivity (and high enantioselectivities/diastereoselectivities). Additionally, with minimal modification of the reaction conditions, alkynes can also undergo tandem hydrogenation-hydroaminocarbonylation to alkyl amides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Inorganic & Nuclear
Dongpo Lu, Chenhui Chen, Lixuan Zheng, Jiale Ying, Zhan Lu
Summary: In this study, a cobalt-catalyzed hydroboration of vinyl-cyclopropanes was reported, providing access to homoallylic boronates with excellent regio- and stereoselectivity. The reaction exhibited a broad substrate scope and could be scaled up to gram level. The authors proposed possible mechanisms and models to explain the selectivity.
Article
Multidisciplinary Sciences
Xianqing Wu, Chenglong Wang, Ning Liu, Jingping Qu, Yifeng Chen
Summary: Carbonylative reactions with CO gas are crucial in organic synthesis. In this study, the authors demonstrate a three-component tandem acylzincation/cyclization reaction using an earth-abundant nickel catalyst and 1 atm of CO gas under mild conditions.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Guangming Wei, Yue Sun, Dongling Zheng, Shiqi Qiu, Zhengkai Chen, Xiao-Feng Wu
Summary: A heating-induced desulfurization annulation of CF3-imidoyl sulfoxonium ylides and isothiocyanates has been developed for the synthesis of 2-trifluoromethylquinolines. The reaction proceeds under metal- and additive-free conditions, providing various biologically valuable derivatives with high efficiency.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Fengqian Zhao, Jian-Xing Xu, Fu-Peng Wu, Xiao-Feng Wu
Summary: This communication describes a copper-catalyzed selectivity-reversed borocarbonylation. In the presence of CuOAc/BuPAd2 catalytic system, a series of unactivated terminal alkenes were transformed into β-boryl ketones in moderate yields, using sterically hindered alkyl bromides as the electrophiles.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Organic
Guangming Wei, Jiajun Zhang, Haoyuan Wang, Zhengkai Chen, Xiao-Feng Wu
Summary: A novel method was developed for the construction of diversely functionalized azaspiro[4,5]-tetraenones and quinolines through the incorporation of CF3 and Se groups into heterocycles. The method exhibited good regioselectivity and its synthetic utility was demonstrated by scale-up reaction and further modification of the obtained products.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Physical
Yuanrui Wang, Xiao-Feng Wu
Summary: A palladium-catalyzed redox-neutral dicarbonylation of terminal alkynes has been developed, using hydroxylamine as both a nucleophile and a potential oxidant. Maleimides were synthesized in moderate yields under relatively mild conditions without the addition of equivalent oxidants. This reaction involves Pd-H addition to the alkyne and the role of hydroxylamine ester intermediate as an internal oxidant via nucleophilic attack.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Physical
Da-Lie An, Le-Cheng Wang, Youcan Zhang, Xiao-Feng Wu
Summary: A new method for synthesizing esters via cobalt-catalyzed carbonylative acetylation of phenols has been developed. In this approach, DTBP serves as the methyl source and reacts with various phenols under low CO pressure (5 bar), resulting in moderate to good yields of the desired esters.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Physical
Fengxiang Zhu, Jiajia Luo, Xiao-Feng Wu
Summary: In this study, a novel copper-catalyzed direct carbodiazenylation method was developed for the synthesis of alkylarylazo compounds. The reaction is carried out under redox neutral conditions, allowing the use of highly functionalized substrates and producing a wide range of diazenes in moderate to good yields. Importantly, this process enables the straightforward preparation of indoles under mild conditions.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Physical
Chang-Sheng Kuai, Bing-Hong Teng, Rui Lai, Yingying Zhao, Guohui Li, Xiao-Feng Wu
Summary: A new method has been developed for the dicarbonylation of amines using the catalytic ending PdII-H in a buffer condition, allowing two incompatible catalytic systems to work simultaneously. This protocol shows excellent regioselectivity and broad substrate scope. Combined experimental and computational studies reveal that the reaction proceeds through a Pd0/PdII-H relay-catalytic cycle.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Physical
Youcan Zhang, Zhi-Peng Bao, Chang-Sheng Kuai, Xiao-Feng Wu
Summary: Here, we have developed a direct and effective synthesis strategy for sulfur-containing carboxylic acid derivatives through copper/visible light catalyzed ring-opening carbonylation of sulfonium salts. The protocol utilizes photoredox to selectively cleave the C(sp3)-S bond of sulfonium salts, while sequentially functionalizing to form vicinal C-C and C-X (X = O or N) bonds in the presence of carbon monoxide and nucleophiles. Various substrates were successfully transformed into desired carbonylated products with moderate to good yields, displaying good functional group tolerance and excellent chemoselectivity. Importantly, this approach can be easily extended to late-stage modification of bioactive molecules.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Organic
Le-Cheng Wang, Nai-Xian Sun, Chang-Sheng Wang, Kai Guo, Xiao-Feng Wu
Summary: The direct concurrent installation of amide and ester groups across olefin motifs is a powerful and promising functionalization tool in organic chemistry. Here, a ligand-free cobalt-catalyzed four-component radical relay carbonylative difunctionalization of ethylene for the synthesis of 4-oxobutanoates has been developed, providing a highly atom-economical approach for the production of valuable C4 building blocks.
Article
Chemistry, Organic
Yiwen Zhu, Jing Wang, Jun Ying, Xiao-Feng Wu
Summary: A cobalt-catalyzed C-H activation and isocyanide insertion reaction of tryptamine derivatives has been developed, leading to the synthesis of indole-2-carboxamide scaffolds. The reaction showed good efficiency in producing a variety of indole-2-carboxamides in moderate to high yields, using Co(OAc)2.4H2O as the non-noble catalyst. Mechanistic experiments revealed the involvement of a Co(III) species as the active catalyst in a non-radical reaction pathway. Notably, the silver salt oxidant could be recycled and reused.
Article
Chemistry, Organic
Xing-Wei Gu, Xiao-Feng Wu
Summary: Transition metal-catalyzed carbonylation of alkyl halides is an efficient method for synthesizing aliphatic carbonyl-containing compounds. This paper discusses recent developments in the carbonylation reactions of alkyl bromides and chlorides catalyzed by abundant metals.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Le-Cheng Wang, Xiao-Feng Wu
Summary: In this study, we have developed an unprecedented and general method for the direct synthesis of various alpha-amino acid derivatives by activating inert C-H bonds. By introducing an appropriate electron-withdrawing group, we successfully modulated the nucleophilicity and polarity of the reaction, resulting in a broad substrate scope and excellent tolerance of sensitive functional groups in this catalytic strategy.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Organic
Yan-Hua Zhao, Xing-Wei Gu, Xiao-Feng Wu
Summary: This paper reports a ligand-free visible-light-induced manganese-catalyzed carbonylation reaction for the synthesis of various amides. The method offers advantages such as low cost and low toxicity, and can proceed effectively at ambient temperature and pressure.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Fengxiang Zhu, Jianxin Xue, Xiao-Feng Wu
Summary: An Fe(II)-catalyzed three-component 1,2-difunctionalization of alkenes with di-tert-butyl peroxide as the methylation reagent has been reported. This method enables 1,2-methylamination and 1,2-methylarylation of various alkenes using nucleophiles such as aromatic amines, pyrrole, and indoles. The simplicity of this protocol allows for the rapid synthesis of complex molecules from simple starting materials.
Article
Chemistry, Physical
Xing Ge, Xiuyu Fang, Ren-Guan Miao, Xinxin Qi, Xiao-Feng Wu
Summary: A general and efficient protocol has been developed for the synthesis of acetamide-functionalized benzofurans using a palladium-catalyzed intramolecular cyclization and reductive aminocarbonylation reaction. The reaction proceeds in a single step, resulting in structure-defined benzofurans with acetamides as attractive functional groups. Various acetamide-functionalized benzofurans were obtained with moderate to good yields and good functional group compatibility using Mo(CO)6 as both CO source and reductant.
JOURNAL OF CATALYSIS
(2023)
