Article
Chemistry, Multidisciplinary
Xueling Liu, Tongshun An, Zhiping Yin, Wenzhou Zhang
Summary: A new palladium-catalyzed reductive double carbonylation of nitroarenes with aryl halides has been developed for the synthesis of benzoxazin-4-ones. This method utilizes Mo(CO)(6) as a reductant and solid carbonyl sources, and can produce benzoxazin-4-one derivatives in moderate to good yields. Importantly, it avoids the use of toxic CO gas and is applicable for late-stage modification of estrone.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Mikhail A. Losev, Andrey S. Kozlov, Vladimir B. Kharitonov, Oleg I. Afanasyev, Fedor S. Kliuev, Ludmila A. Bulygina, Natalya S. Khrushcheva, Dmitry A. Loginov, Denis Chusov
Summary: A simple and selective method using carbon monoxide as a reducing agent was developed for the preparation of amides from nitroarenes and carboxylic acids. The protocol does not require non-gaseous additives, simplifying product isolation and saving reducible functional groups.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Physical
Han-Jun Ai, Fengqian Zhao, Hui-Qing Geng, Xiao-Feng Wu
Summary: The letter discusses a generic method for the synthesis of linear thioesters through palladium-catalyzed thiocarbonylation of alkenes. This approach allows for the straightforward production of desired thioesters from readily available alkenes with moderate to good yields.
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)
Article
Chemistry, Organic
Bhushanarao Dogga, C. S. Ananda Kumar, Jayan T. Joseph
Summary: An efficient protocol has been developed for the reductive carbonylation of (hetero) aryl halides and triflates under CO gas-free conditions using Pd/Co-2(CO)(8) and triethylsilane. The mild reaction conditions, enhanced chemoselectivity, and easy access to heterocyclic and vinyl carboxaldehydes highlight its importance in organic synthesis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Ida Ziccarelli, Raffaella Mancuso, Francesco Giacalone, Carla Calabrese, Valeria La Parola, Alex De Salvo, Nicola Della Ca', Michelangelo Gruttadauria, Bartolo Gabriele
Summary: This article reports the successful heterogenization of the classical PdI(4)(2-)carbonylation catalyst on multi-walled carbon nanotubes. The newly developed heterogeneous catalyst shows good activity and recyclability in the oxidative monoaminocarbonylation reaction, with limited metal contamination in the final organic compounds.
JOURNAL OF CATALYSIS
(2022)
Article
Polymer Science
Li Wei, Bin Huang, Limin Liu, Mingzhong Cai
Summary: A series of high molecular weight poly(amide-imide)s containing cardo structures were successfully synthesized via a supported palladium-catalyzed carbonylation polymerization. These polymers exhibited high thermal stability, excellent mechanical properties, and high optical transparency. The supported palladium catalyst used in the process could be conveniently separated and recycled multiple times without significant loss of catalytic efficiency.
Article
Chemistry, Physical
Jian-Shu Wang, Jiangjie Zhang, Siqi Wang, Jun Ying, Chuan-Ying Li, Xiao-Feng Wu
Summary: A novel palladium-catalyzed domino carbonylative cyclization has been developed for the rapid construction of functionalized heterocycles. The reaction proceeds smoothly with the consecutive formation of C-C and C-X bonds using benzene-1,3,5-triyl triformate as the CO source, yielding a variety of biologically relevant derivatives.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Physical
Dan Wen, Xing Ge, Ren-Guan Miao, Xinxin Qi, Xiao-Feng Wu
Summary: A palladium-catalyzed carbonylative synthesis of carboxamide substituted 2-pynones from methyl enynoates and nitroarenes has been developed. A wide range of carboxamide substituted 2-pynones were obtained in moderate to high yields with quite high functional group compatibility using nitroarenes as the nitrogen sources and Mo(CO)6 as both CO surrogate and reductant. Late-stage modifications of natural molecules were also achieved.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Inorganic & Nuclear
Dong-Kun Li, Bo Zhang, Qi Ye, Wei Deng, Zheng-Yang Xu
Summary: This paper reports an effective ligand-free Pd-catalyzed carbonylation of o-bromoaryl iodides with alkynes to obtain indenone compounds. The reaction shows good tolerance towards functional groups on o-bromoaryl iodides and alkynes. By introducing Mo(CO)6 as a carbonyl source, the reaction becomes safer and more operable. Mechanistic investigations reveal a sequential process of oxidative addition, alkyne insertion, carbonyl insertion, and reductive elimination to produce the desired carbonylation products.
Article
Chemistry, Inorganic & Nuclear
Bo Zhang, Wei Deng, Zheng-Yang Xu
Summary: In this article, a method for the synthesis of N,N'-diphenyl urea and N-phenyl carbamate by transition-metal-catalyzed carbonylation is introduced. The reaction proceeds through sequential amine C-H bond activation, carbonyl insertion, nucleophilic attack, and oxidation. Moreover, the indenones obtained with Mo(CO)6 as a CO surrogate can be functionalized to form synthetic useful derivatives.
Article
Chemistry, Physical
Jiangjie Zhang, Jun Ying, Xiao-Feng Wu
Summary: A novel palladium-catalyzed tandem cyclization and carbonylation reaction was developed for the synthesis of indeno[1,2-b]indol-10(5H)-one derivatives. The reaction proceeded smoothly with high yields using formic acid as the CO source. This method can also be applied for the modification of various bioactive molecules.
JOURNAL OF CATALYSIS
(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, Organic
Mikhail A. Losev, Andrey S. Kozlov, Vladimir B. Kharitonov, Oleg I. Afanasyev, Fedor S. Kliuev, Ludmila A. Bulygina, Natalya S. Khrushcheva, Dmitry A. Loginov, Denis Chusov
Summary: A straightforward and selective method using carbon monoxide as a reductant was developed to prepare amides directly from nitroarenes and carboxylic acids. This protocol simplifies product isolation by not requiring any non-gaseous additives and preserves reducible functional groups.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yong-Wang Huo, Xinxin Qi, Tiefeng Xu, Wangyang Lu, Xiao-Feng Wu
Summary: Alkynones are important building blocks found in biologically active compounds and play a key role in the synthesis of natural products and heterocycles. While traditional methods involve reactions between acid chlorides and terminal alkynes, drawbacks such as high reaction temperature and poor functional group tolerance still exist.
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)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.