Article
Chemistry, Organic
Huihong Wang, Fei Cao, Weiwei Gao, Xiaodong Wang, Yuhang Yang, Tao Shi, Zhen Wang
Summary: Epoxides have been utilized as alkylating reagents in Pd(II)-catalyzed C-H alkylation and oxidative annulation to synthesize isoquinolones instead of isochromans. By modifying the reaction mechanism with the addition of oxidant and TEA, various isoquinolones have been successfully prepared with high yields up to 92%. This methodology has also been applied in the total syntheses of rupreschstyril, siamine, and cassiarin A in an efficient manner.
Article
Chemistry, Organic
Atul Kumar, Gulenur N. Khatun, Rodney A. Fernandes
Summary: An efficient, mild, and economical approach for the regioselective synthesis of 4-aryl/alkyl-1-peroxy-but-3-en-2-ols from 1-substituted-1,3-butadienes using hydroperoxides and catalyzed by TBAI has been achieved. This method is simple to operate, does not require dry conditions, and has excellent tolerance to a wide range of substrates, resulting in good yields of corresponding hydroxyperoxidates. Thus, an outstanding regioselective orthogonal dioxygenation in a diene system has been accomplished.
Article
Chemistry, Organic
Qing-Feng Xu-Xu, Yuji Nishii, Masahiro Miura
Summary: In this study, a Rh-catalyzed direct diarylation of selenium with benzamide derivatives was reported. Elemental selenium was used as the Se source, allowing for easy synthesis of diarylselenides with amide moieties through directed C-H activation. Control experiments indicated the intermediacy of electrophilic Se(IV) species.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Wenwei Li, Ruxue Wang, Zhefeng Li, Jiuxi Chen, Yuhong Zhang, Ningning Lv
Summary: An unprecedented method of nickel-catalyzed dual C(sp(2))-H amination of N-quinolylbenzamides with benzohydroxamic acids has been developed to access triarylamines in one pot. Broad-spectrum hydroxylamine is employed as an amino source for C-H amination, showing good chemo-selectivity and functional group tolerance. Furthermore, the catalytic system can be extended to N-(pivaloyloxy)benzamide, dioxazolone, isocyanate, and aniline for C-H amination.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Bang-An Zhou, Chun-Lin Zhang, Song Ye
Summary: Researchers have developed an NHC-catalyzed benzannulation reaction for the synthesis of benzotrifluorides using enals and beta-trifluoromethylenones. This reaction involves a [4 + 2] annulation/lactonization/decarboxylation/oxidative aromatization cascade catalyzed by NHC. The reaction shows mild conditions, excellent functional group compatibility, and exclusive regioselectivity, resulting in the formation of multi-substituted benzotrifluorides in moderate to good yields.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Bitan Sardar, Ramen Jamatia, Arup Samanta, Dipankar Srimani
Summary: An efficient Ru doped hydrotalcite catalyst was used for the N-alkylation of benzamides and sulfonamides with alcohols via borrowing hydrogen catalysis. The reaction showed good to excellent yields with various primary alcohols. Mechanistic studies revealed that the reaction proceeds via a borrowing hydrogen pathway. The catalyst also demonstrated the capability to directly synthesize quinazolinone and exhibited successful recyclability and high reactivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Shubham Tiwari, Sandeep Chandrashekharappa, Guddeangadi N. Gururaja
Summary: A mild, catalyst and oxidant-free protocol was reported for efficient synthesis of alpha-ketothioamides with a broad substrate scope. The confined reactivity of amines was demonstrated, and the anti-cancer ketothioamides were successfully synthesized.
ORGANIC & BIOMOLECULAR CHEMISTRY
(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
Biochemistry & Molecular Biology
Francesca Begini, Renata A. Balaguez, Allya Larroza, Eric F. Lopes, Eder Joao Lenardao, Claudio Santi, Diego Alves
Summary: This study presents a simple method to synthesize 4-arylselanyl-1H-1,2,3-triazoles from selenium-containing carbinols in a one-pot strategy, with moderate to good yields including quinoline and Zidovudine derivatives. One-pot protocols are essential for addressing concerns about waste production and solvent consumption, while also producing interesting by-products with alkynylselenium moieties connected to the triazole.
Article
Chemistry, Organic
Dhirendra Kumar, Suresh Kumar Maury, Savita Kumari, Arsala Kamal, Himanshu Kumar Singh, Sundaram Singh, Vandana Srivastava
Summary: A new green approach for the synthesis of amide was developed through TBAI-catalyzed oxidative coupling of benzyl bromides with amine using tert-butyl hydroperoxide as an oxidant. Various electron-donating and withdrawing groups were subjected to the reaction, leading to the formation of amide in good to excellent yields.
SYNTHETIC COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Rapelly Venkatesh, Adesh Kumar Singh, Yong Rok Lee, Jeyakumar Kandasamy
Summary: The method described involves the preparation of alpha-aryl acetophenones from styryl ethers and aryldiazonium salts, catalyzed by palladium acetate at room temperature without the need for ligand or base. The method is highly attractive in terms of reaction conditions, substrate scope, functional group tolerance, and yields, as demonstrated by the synthesis of alpha-aryl indoles and 3-aryl isocoumarin from styryl ethers.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Shengxian Zhai, Shuxian Qiu, Shuai Yang, Bingyan Hua, Yongsheng Niu, Chuchu Han, Youzhu Yu, Yuchao Li, Hongbin Zhai
Summary: A metal-free radical cascade reaction was developed for the synthesis of arylsulfonyl-substituted indolo[2,1-a]isoquinolin-6(5H)-one derivatives using readily available sulfonyl hydrazides and N-substituted 2-aryl indoles. The reaction employed a TBAI-TBHP catalytic system and yielded a broad series of structurally diverse derivatives in moderate to excellent yields. The reaction exhibited mild reaction conditions, operational ease, scalability, and high tolerance towards functional groups.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Shibo Xu, Koji Hirano, Masahiro Miura
Summary: The study reveals a nickel-catalyzed C-H coupling of 8-aminoquinoline-derived benzamides with aryl- and alkyl-substituted aziridines, providing direct access to benzolactams through a C-H alkylation-intramolecular amidation cascade event with removal of the aminoquinoline auxiliary. The regioselectivity of ring opening of aziridines can be controlled by substituents, and the reaction with chiral aziridines proceeds with inversion of configuration, suggesting an S(N)2-type nucleophilic ring-opening pathway.
Article
Chemistry, Multidisciplinary
Pham Duy Quang Dao, Jun-Hyun Park, Ho-Jin Lim, Chan Sik Cho
Summary: Cyclopentenyl carbinols are oxidatively cleaved and cyclized to form terpenylic acid analogues in good yields in the presence of oxone and sodium periodate.
Article
Chemistry, Organic
Andreas Stumpf, Di Xu, Tyler A. Tuck, Haiming Zhang
Summary: A protecting-group-free synthesis of 3-aryl-substituted 4-aminopyrazoles from acetophenones has been demonstrated. The synthesis tolerates a broad range of substrates.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Zhiping Yin, Weidong Shi, Xiao-Feng Wu
Summary: This review presents the advances in transition-metal-catalyzed carbonylative multifunctionalization of alkynes, which is of great significance for the construction of multisubstituted carbonyl-containing derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Siqi Wang, Jian-Shu Wang, Jun Ying, Xiao-Feng Wu
Summary: A novel Pd-catalyzed carbonylative cyclization reaction of alkene-tethered indoles with phenols or aryl-boronic acids is reported, providing a facile access to indolo[2,1-a]isoquinoline scaffolds. This method utilizes benzene-1,3,5-triyl triformate (TFBen) as a CO surrogate for incorporating a carbonyl group into the indolo[2,1-a]isoquinoline framework, affording various carbonyl-containing indolo[2,1-a]isoquinoline derivatives in good yields.
CHINESE CHEMICAL LETTERS
(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, Organic
Chang-Sheng Kuai, Bing-Hong Teng, Da-Lie An, Yingying Zhao, Xiao-Feng Wu
Summary: A palladium-catalyzed carbonylation of 2-trifluoromethyl-1,3-enynes has been developed, providing access to multisubstituted conjugated dienes. This method exhibits excellent regio- and exclusive (E)-stereoselectivity and demonstrates broad substrate scope with both amines and alcohols as reaction partners, showing promising functional group tolerance.
Article
Chemistry, Organic
Siqi Wang, Shuwei Li, Liangcai Liu, Jun Ying, Xiao-Feng Wu
Summary: Amide-containing indolo-[2,1-a]isoquinoline scaffolds were synthesized by palladium-catalyzed carbonylative cyclization of alkene-tethered indoles with nitro-arenes. Using Mo(CO)6 as the CO source and reductant, and nitroarenes as the nitrogen source, this reaction yielded various amide-containing indolo[2,1-a]isoquinoline derivatives in good yields. Additionally, the late-stage modifications of bioactive molecules using this protocol were demonstrated.
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, Organic
Ping Wei, Yiwen Zhu, Jun Ying, Xiao-Feng Wu
Summary: Cobalt(II) salt has been widely used as a non-noble metal catalyst for direct C-H bond functionalization. In this study, we developed a cobalt-catalyzed reaction for the rapid construction of 2-alkoxylindole scaffolds from the C-H cleavage and alkoxylation of indoles with alcohols. The reaction proceeded well with Co(acac)2 as the catalyst, yielding a variety of 2-alkoxylindole derivatives in moderate to high yields. Control experiments suggested a radical process involving Co(III) species as the active catalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Editorial Material
Chemistry, Organic
Xiao-Feng Wu, Paul J. Dyson, Bruce A. Arndtsen
JOURNAL OF ORGANIC CHEMISTRY
(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
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
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
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
