Article
Chemistry, Organic
Jun Li, Zhi-Wen Zhao, Shuang Zheng, Ping He, Ji-Ying Qiu, Quan-Quan Zhou, Zhi-Lin Ren
Summary: Herein, we describe a novel one-pot method for the synthesis of polysubstituted pyrrole derivatives via a three-component reaction of alkenyl bromides, amines, and isocyanides. The conversion process is catalyzed by a Pd catalyst without the need for additional ligands. The key feature of this method is the orderly insertion of three isocyanide molecules, directed by the intramolecular imine group. Additionally, DFT calculations provide support for the proposed reaction mechanism.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Joseph Brehm, Richard J. Lewis, Thomas Richards, Tian Qin, David J. Morgan, Thomas E. Davies, Liwei Chen, Xi Liu, Graham J. Hutchings
Summary: The combination of an evolved unspecific peroxygenase (UPO) and bimetallic Pd-based catalysts is highly effective for the oxidative valorization of cyclohexane. Alloying Pd with Zn enhances catalytic performance, while the large population of Pd-only clusters in other catalysts promotes undesired oxidation products.
Article
Chemistry, Physical
Joseph Brehm, Richard J. Lewis, Thomas Richards, Tian Qin, David J. Morgan, Thomas E. Davies, Liwei Chen, Xi Liu, Graham J. Hutchings
Summary: The combination of an evolved unspecific peroxygenase (UPO) from Agrocybe aegerita and bimetallic Pd-based catalysts shows high efficiency in the oxidation of cyclohexane. The alloying of Pd with Zn greatly enhances the catalytic performance, attributed to the formation of PdZn alloys and electronic modification of Pd. This system inhibits competitive chemo-catalyzed H2O2 degradation reactions and overoxidation of cyclohexanol.
Article
Chemistry, Physical
Yang Shen, Zhen-Yao Dai, Cheng Zhang, Pu-Sheng Wang
Summary: A rapid synthetic method for a target compound has been developed by combining photocatalysis and palladium catalysis, demonstrating an atom-economic and environmentally friendly strategy. Experimental results suggest that this method has high synthetic utility.
Article
Chemistry, Applied
Linhao Liu, Henri Doucet
Summary: The reactivity of 1,2-dihalobenzenes in palladium catalyzed polyheteroarylation via C-H bond functionalization was investigated. The first catalytic cycle using thiophene as the heteroarene gives the expected 2-(2-bromophenyl)thiophenes. In the course of the second catalytic cycle, in the presence of heteroarenes having a free C3-position, a partial Pd-1,4-migration occurred giving rise to aryl-substituted biheteroarenes such as 2 '-aryl-2,3 '-bithiophenes as well as the expected 1,2-di(thiophen-2-yl)benzenes. The best selectivities in favor of the formation of 2 '-aryl-2,3 '-bithiophenes were obtained with electron-rich 1,2-dihalobenzenes. A wide variety of thiophene derivatives bearing useful functions such as formyl, acetyl, cyclopropylmethanone, 2-methyl-1,3-dioxolane, ester, nitrile or chloro was tolerated allowing to prepare poly-functionalized 2 '-aryl-2,3 '-bithiophenes. Moreover, this one pot preparation of 2 '-aryl-2,3 '-bithiophenes employs a low loading of an air stable commercially available palladium source associated to an inexpensive base.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Fei Ma, Jie Li, Shuning Zhang, Yuang Gu, Tingting Tan, Wanting Chen, Shuyue Wang, Hongtao Xu, Guang Yang, Richard A. Lerner
Summary: Metal-catalyzed one-pot reaction using DNA encoding has been developed for the formation of C(sp(2))-C(sp(3)) and C(sp(3))-S bonds. The reaction shows wide substrate scopes and moderate to excellent yields, greatly expanding the chemical space of DNA-compatible reactions and the molecular scaffold diversity of DNA-encoded libraries.
Article
Chemistry, Multidisciplinary
Jasem Aboonajmi, Masoumeh Mohammadi, Farhad Panahi, Mahdi Aberi, Hashem Sharghi
Summary: An efficient one-pot, three-component process has been developed using a catalytic amount of Fe(iii) porphyrin for the synthesis of benzimidazole derivatives. The reaction involves domino C-N bond formation and cyclization reactions of benzo-1,2-quinone, aldehydes, and ammonium acetate as a nitrogen source, leading to the selective production of benzimidazole. Several benzimidazole derivatives have been successfully synthesized with high yields using this method under mild reaction conditions.
Article
Chemistry, Multidisciplinary
Lei Zhang, Liming Cao, Maolin Sun, Chaoming Liang, Lei Yang, Yueyue Ma, Ruihua Cheng, Jinxing Ye
Summary: A straightforward synthesis approach to chiral 1-aryl-2-aminoethanols via the one-pot asymmetric hydrogenation catalyzed by Ir catalyst was developed. This tandem process involves the in situ generation of alpha-amino ketones via the nucleophilic substitution of alpha-bromoketones with amines and the Ir-catalyzed asymmetric hydrogenation of ketone intermediates to provide diverse enantiomerically enriched beta-amino alcohols. The excellent yields and enantioselectivities (up to 96 % yield and up to >99 % ee) with a wide substrate scope in this one-pot strategy were obtained.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Yuanyun Gu, Yan-En Wang, Yaqi Yuan, Haodong Xu, Yizhou Lu, Yufei Zhang, Fei Xue, Dan Xiong, Jianyou Mao
Summary: The deprotonation of allylbenzene was achieved using a catalytic alkali amide base, and the resulting allyl anion was trapped by N-(trimethylsilyl) aldimines to synthesize homoallylic amines. This one-pot method provided value-added products with excellent selectivity without the need for protection groups on the imines.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jian Zhang, Xinzhe Shi, Henri Doucet
Summary: This study explores a Pd-catalyzed annulative pi-extension reaction of 1-arylpyrroles using 1,2-dihalobenzenes as coupling partners, leading to the selective synthesis of pyrrolo[1,2-f]phenanthridines. The higher reactivity of the pyrrole C2-H bond allows for successful access to substituted pyrrolo[1,2-f]phenanthridines.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jin Wang, Chong Yin, Wenjia Han, Yaohong Ma, Yanchao Yin, Peiyu Zhao, Yahui Song, Jihui Zhang
Summary: The platinum group metals have unique properties and are often combined with a second metal to reduce cost and enhance activity. This study introduces a method for synthesizing Au-based nanocrystals by adding PGM anion precursors to a solution containing in situ Au nanowires without the need for additional reducing agents. This work opens up new possibilities for the manufacturing of Au-based nanocrystals with low PGM content.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Wei Wu, Beibei Luo, Yi You, Zhiqiang Weng
Summary: A novel synthesis approach for the construction of 2-trifluoroethyl-substituted benzofurans under copper-catalyzed conditions has been developed, with moderate to excellent yields (up to 93%). This method is also applicable to the formation of 2-trifluoroethylated indoles.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Subrata K. Ghosh, Mengnan Hu, Robert J. Comito
Summary: The method describes a mild and selective protocol for preparing primary and secondary aliphatic amines in a single pot based on intermolecular sp(3) C-H imination. It constitutes a selective method for complex amine synthesis and a new mechanistic platform for C-H amination. This work demonstrates useful site selectivity within substrates bearing multiple sp(3) C-H bonds.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Huy Tran, Guillaume Revol, Alyson Poyser, Louis Barriault
Summary: In this study, a novel Lewis acid gold catalyst was used to generate synthetically challenging polycyclic scaffolds through a one-pot cascade sequence. By controlling the ligand and reaction conditions, both 6,6,5-tricyclic and 6,6,6,5-tetracyclic cores were selectively synthesized in one operation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Ali Osman Karatavuk
Summary: A highly efficient method for the synthesis of 2-pyridonyl alcohols via a gold(i) catalyst and methanesulfonic acid has been developed. The proposed mechanism involves intramolecular cyclization product formation, leading to the formation of N-alkenyl pyridonyl alcohols in moderate to excellent yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xiufang Cheng, Huamin Wang, Fuhong Xiao, Guo-Jun Deng
Article
Chemistry, Organic
Huamin Wang, Wei Zhou, Mengna Tao, Anjing Hu, Junliang Zhang
Article
Chemistry, Organic
Huamin Wang, Xiangxiang Cao, Fuhong Xiao, Saiwen Liu, Guo-Jun Deng
Article
Chemistry, Organic
Huamin Wang, Jinhui Cai, Huawen Huang, Guo-Jun Deng
Article
Chemistry, Multidisciplinary
Huamin Wang, Li Zhang, Youshao Tu, Ruiqi Xiang, Yin-Long Guo, Junliang Zhang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Huamin Wang, Junyou Zhang, Youshao Tu, Junliang Zhang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Multidisciplinary Sciences
Huamin Wang, Xiuzheng Li, Youshao Tu, Junliang Zhang
Article
Chemistry, Organic
Huamin Wang, Yibo Wei, Yuqiang Li, Shuangshuang Long, Li-Juan Sun, Shixiong Li, Ying-Wu Lin
Summary: A new strategy for the enantioselective synthesis of axially chiral N-aryl succinimides was developed using [3 + 2] annulation of MBH carbonates and N-aryl maleimides under chiral phosphine. This process allows for the efficient construction of stereogenic carbon centers and remote C-Ar-N atropisomeric chirality. The method exhibits mild reaction conditions, high efficiency, scalability, and a broad substrate scope.
Article
Chemistry, Inorganic & Nuclear
Li-Juan Sun, Huamin Wang, Jia-Kun Xu, Shu-Qin Gao, Ge-Bo Wen, Ying-Wu Lin
Summary: This study presents the design and construction of a double mutant human neuroglobin (Ngb) that can efficiently catalyze carbene N-H insertions for aromatic amine and o-phenylenediamine derivatives, leading to high yields and total turnover numbers. It also demonstrates the first example of quinoxalinone formation catalyzed by an engineered heme enzyme.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Huamin Wang, Wenjing Niu, Yongjun He, Yibo Wei, Xianxian Li, Ying-Wu Lin
Summary: We report a general and effective system for the cyclization of beta-trifluoromethyl enones with amidines using 1,3-diiodo-5,5-dimethylhydantoin (DIH) as a catalyst. This reaction provides a range of trifluoromethylated 2-imidazolines in high yields and good diastereoselectivities, with good tolerance towards functional groups. Additionally, a one-pot synthesis of trifluoromethylated imidazoles via sequential cyclization and oxidation is demonstrated. The reaction mechanism is verified by ESI-MS studies, confirming a reasonable proposed mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Youshao Tu, Honglin Dong, Huamin Wang, Yuhui Ao, Yu Liu
Summary: A method for azidation of beta-fluoroalkyl alpha,beta-unsaturated ketones has been developed, allowing access to a wide variety of fluorinated nitrogenous carbonyl compounds. The strategy does not involve any metallic or organic catalysts, and the choice of solvents can modulate the reaction outcomes to produce either beta-azido ketones or beta-amino alpha-diazo ketones. The reaction system is environmentally friendly, operates under mild conditions, is simple, and exhibits excellent functional group tolerance.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Tiantian Cong, Huamin Wang, Xiuzheng Li, Hai-Hong Wu, Junliang Zhang
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Huamin Wang, Weike Lu, Junliang Zhang
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
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)