Article
Chemistry, Organic
Jian Wang, Yini Chen, Wanting Du, Ningyao Chen, Kang Fu, Qijun He, Liming Shao
Summary: This paper presents an efficient metal-free method for the oxidative rearrangement of indoles, leading to the formation of various organic compounds. The protocol exhibits a broad substrate scope and functional group tolerance, and has been successfully applied in natural product synthesis.
Article
Chemistry, Organic
Hang Xu, Sho Yamaguchi, Takato Mitsudome, Tomoo Mizugaki
Summary: In this study, the catalytic oxidative trimerization and oxygenative cleavage reactions of indoles were achieved using a copper nitride nanocube catalyst, producing valuable nitrogen-containing compounds such as indolin-3-ones and 2-ketoanilides under additive-free conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Suvendu Halder, Rupa Bai Addanki, Pavan K. Kancharla
Summary: The alkene-based o-[1-(p-MeO-phenyl)vinyl]benzoates (PMPVB) donors have been successfully used for the regio- and stereoselective synthesis of C-linked indolyl glycosides under catalytic Bronsted acidic conditions. The highly reactive glycosyl donors enable the use of poorly nucleophilic N-Boc and N-acetyl indole derivatives, resulting in excellent yields and stereoselectivities of the indolyl glycosides. Furthermore, conditions for recycling the byproduct have been developed, significantly improving the potential of these donors.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Letian Zhang, Jiajun He, Jiabin Shen, Hao Xu, Dancheng Zhu, Chao Shen
Summary: A one-pot stepwise Ce(III)/photoassisted cross-dehydrogenative coupling/fluorooxidation process was developed to efficiently construct C3-heteroaryl 3-fluorooxindoles. This method utilized readily available chemical feedstocks and did not require the use of precious metals, oxidants, or additives. The products were obtained in moderate-to-good yields through recrystallization with favorable functional group compatibility. Additionally, this methodology successfully established C-C, C=O, and C-F bonds in a single step, providing a direct transformation of C=C bonds to functionalized C-C bonds.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Polymer Science
Eliraz Stamker, Oshrat Levy-Ontman, Adi Wolfson
Summary: The novel heterogeneous catalyst prepared using a non-toxic, renewable, and biodegradable support exhibited high activity, good selectivity, and recyclability.
Article
Chemistry, Inorganic & Nuclear
Kai Li, Ying Ye, Wenchao Zhang, Yudong Zhang, Chao Liu
Summary: Environmentally friendly phosphors with narrow-band green luminescence were developed by preparing nanocrystals in glass. The addition of Zn can change the emission color and enhance the quantum yield. These materials also exhibit good thermal and chemical stabilities, making them suitable for use in solid-state lighting and backlight display applications.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Peng Zhang, Qi Xu, Xiao-Mei Wang, Jia Feng, Chuan-Jun Lu, Yingzi Li, Ren-Rong Liu
Summary: The first enantioselective synthesis of N-N bisindole atropisomers via palladium-catalyzed construction of one indole skeleton is reported in this study. A wide variety of N-N axially chiral bisindoles were generated with good yields and excellent enantioselectivities through a cascade condensation/N-arylation reaction. The reaction mechanism and enantiocontrol were further investigated using density functional theory (DFT) calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Guoqiang Yang, Jiaoting Pan, Ya-Ming Ke, Yongbing Liu, Yu Zhao
Summary: An efficient tandem catalysis method has been developed for the direct conversion of alcohol-containing alkynyl anilines to valuable chiral 2,3-fused tricyclic indoles. Highly diastereoselective transformations of the tricyclic indole products also provide efficient access to a diverse array of complex polycyclic indoline compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Qingzhao Xing, Zhe Hao, Jing Hou, Gaoqiang Li, Ziwei Gao, Jing Gou, Chaoqun Li, Binxun Yu
Summary: This study presents a manganese-catalyzed oxidation reaction for furans with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide under mild conditions with wide functional group compatibility.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yufeng Chen, Ruitong Yang, Fuhong Xiao, Tianci Xu, Guojiang Mao, Guo-Jun Deng
Summary: A three-component strategy using indole-2-carboxaldehydes, aromatic aldehydes, and ammonium acetate as starting materials was developed for the preparation of 3-phenyl-9H-imidazo-[1,5-a]-indol-9-one under copper catalysis conditions. This strategy involved the selective oxidation of the C3 position in the indole substrate into a ketone skeleton using oxygen as the sole oxidant and ammonium acetate as the nitrogen source, resulting in the formation of a new five-membered ring. Similar reaction conditions also allowed the synthesis of the same products from indole-2-carboxaldehydes and benzyl amines.
Article
Chemistry, Multidisciplinary
Illia Lenko, Alexander Mamontov, Carole Alayrac, Remi Legay, Bernhard Witulski
Summary: The research demonstrates the divergent Pd-catalyzed reaction cascades with various 1,3-diynamides, leading to different products depending on the presence or absence of TBAF. Furthermore, deuterium labeling experiments reveal the unique formation mechanism of the products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Natalia Llopis, Patricia Gisbert, Alejandro Baeza
Summary: The use of HFIP solvent in the oxidative cleavage of indoles results in higher yields of 2-ketoacetanilides, and it is also suitable for oxidation of various pyrroles and furans derivatives. The sustainable and practical nature of HFIP is demonstrated by its successful recycling up to 4 cycles in larger-scale reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Dominik Neukum, Lorena Baumgarten, Dominik Wust, Bidyut Bikash Sarma, Erisa Saraci, Andrea Kruse, Jan-Dierk Grunwaldt
Summary: This study investigated the oxidation of unrefined HMF solutions obtained from saccharides in chicory roots, showing the critical role of base in increasing FDCA yield and the significant influence of amino acids from bio-sources on catalytic activity. A supported AuPd(2:1)/C alloy catalyst exhibited superior activity and stability.
Article
Chemistry, Organic
Yueyue Fan, Jingwen Guo, Yuting Bao, Yuxin Yuan, Meng Hu, Xiaohui Li, Hang Yan, Yuepiao Cai, Qinqin Xia
Summary: We have developed an efficient and green synthesis strategy for the production of 2-substituted indolin-3-ones, which can be used to functionalize a range of complex pharmaceuticals. This research is of great significance for medicinal chemistry programs.
Article
Chemistry, Multidisciplinary
Clotilde Placais, Sherif J. Kaldas, Morgan Donnard, Armen Panossian, David Bernier, Sergii Pazenok, Frederic R. Leroux
Summary: This work presents the synthesis of aryl and alkenyl halides from fluorosulfonates using commercially available ruthenium catalysts. It is the first study to efficiently convert phenols to aryl halides with chloride, bromide, and iodide. Fluorosulfonates can be easily prepared using sulfuryl fluoride (SO2F2) and cost-effective substitutes for triflates. Additionally, this work also reports an efficient coupling of alkenyl fluorosulfonates for the first time. Representative examples demonstrate that the reaction can be carried out in a one-pot process, starting directly from phenol or aldehyde.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Lian-Dong Guo, Zejun Xu, Rongbiao Tong
Summary: The asymmetric total syntheses of three paspaline-derived IDTs were reported, featuring green Achmatowicz rearrangement/bicycloketalization and cascade ring-closing metathesis of dienyne, as well as four palladium-mediated reactions. These synthetic strategies are expected to facilitate the chemical synthesis of other paspaline-derived IDTs and further bioactivity studies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Organic
Hongling Wang, Yonggui Robin Chi, Xuan Huang
Summary: N-heterocyclic carbene (NHC) catalysis is a versatile strategy for building molecules, and has been studied in combination with other catalytic agents to enhance reactivity and yield.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Jianjian Liu, Mali Zhou, Rui Deng, Pengcheng Zheng, Yonggui Robin Chi
Summary: The authors report a synthetic method for the asymmetric synthesis of chiral sulfoxides using intramolecular chalcogen bonding interactions. The reaction involves conformational locking and facile isomerization enabled by chalcogen bonding interactions, leading to the formation of chiral sulfoxide products with excellent optical purities.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Mali Zhou, Jianjian Liu, Rui Deng, Qingyun Wang, Shuquan Wu, Pengcheng Zheng, Yonggui Robin Chi
Summary: A catalytic strategy for asymmetric synthesis of chiral tetrasubstituted silicon-stereogenic silanes is disclosed. By using a covalently symmetric silane as the substrate and a N-heterocyclic carbene catalyst, the substrate can be selectively activated and undergo desymmetrization reaction to afford optically enriched products.
Article
Chemistry, Multidisciplinary
Xing Yang, Liwen Wei, Yuelin Wu, Liejin Zhou, Xinglong Zhang, Yonggui Robin Chi
Summary: In this study, a novel bridged biaryl containing medium-sized rings was selectively synthesized via N-heterocyclic carbene organocatalysis. The reaction began with the addition of the carbene catalyst to the aminophenol-derived aldimine substrate, followed by oxidation and intramolecular desymmetrization to form 1,3-oxazepine-containing bridged biaryls with high yields and excellent enantioselectivities. These products can be readily transformed into chiral phosphite ligands.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jie Lv, Zhichao Jin, Hongling Wang, Yonggui Robin Chi
Summary: This review systematically summarizes the carbon-sulfur (C-S) bond formation reactions enabled by N-heterocyclic carbene (NHC) organocatalysis, including S-esterification, nucleophilic S-conjugate addition, S-addition reactions with electrophiles, and C-S bond formations via cooperative NHC/transition metal-catalyzed radical reactions. The review also provides the authors' own comprehension and perspectives on this highly active research field.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Multidisciplinary
Peilin Tian, Rongbiao Tong
Summary: The Suzuki coupling of haloarenes with arylboronic acids is a crucial C-C bond-forming reaction in organic chemistry. By replacing the pre-functionalized haloarenes with arenes for the oxidative coupling, a milder and more environmentally friendly approach to the classical Suzuki reaction has been achieved. This involves conducting the reaction in water using hydrogen peroxide as the oxidant, which eliminates the use of flammable organic solvents and generates water as the only byproduct. The strategy has been successfully applied to expand the utility of green chemistry in organic synthesis, including two cross-dehydrogenative couplings.
Article
Chemistry, Organic
Liyan Song, Yiqin Zhou, Hanbin Liang, Hongzuo Li, Yunrong Lai, Hongliang Yao, Ran Lin, Rongbiao Tong
Summary: Semipinacol rearrangement is a valuable method for the synthesis of natural products and construction of highly congested quaternary carbons. Here, a safe and green protocol for halogenative semipinacol rearrangement is reported, which offers the advantages of easy operation and insensitivity to air and moisture.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Rongbiao Tong
Summary: This Account presents the use of two synthetic strategies (Phenol Oxidative Dearomatization, POD; and Fur an Oxidative Dearomatization, FOD) in the total synthesis of natural products. It focuses on how these total synthesis projects are conceived and connected from the perspective of laboratory development. Total synthesis is shown to be a connecting and inspirational point that sparks new ideas and projects.
Article
Chemistry, Multidisciplinary
Wai Fung Cheng, Shiqiang Ma, Yin Tung Lai, Yuen Tsz Cheung, Kornkamon Akkarasereenon, Yiqin Zhou, Rongbiao Tong
Summary: An intramolecular aza-Prins cyclization of aza-Achmatowicz rearrangement products was developed using bismuth tribromide as both an efficient Lewis acid and a bromide nucleophile source. This approach enables the construction of highly functionalized 9-azabicyclo[3.3.1]nonanes, which are valuable building blocks for alkaloid natural products and drug molecules. The application of this method to the total synthesis of six indole alkaloids demonstrates its significant synthetic utility.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Medicinal
Wenjun Wang, Foqing Ma, Yuen Tsz Cheung, Guihua Zeng, Yiqin Zhou, Zijing Chen, Lixin Liang, Tuoping Luo, Rongbiao Tong
Summary: Induction of ferroptosis has been found to be an effective method for cancer treatment. In this study, marine alkaloid lepadins E and H were discovered as new ferroptosis inducers. In vitro experiments showed that lepadins E and H exhibited significant cytotoxicity and induced ferroptosis through the p53-SLC7A11-GPX4 pathway. Animal model studies further confirmed their in vivo antitumor efficacy. This discovery highlights the potential of lepadins as a new class of ferroptosis inducers for anticancer therapy.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Tao Zheng, Jun Xu, Shaojun Cheng, Jianghai Ye, Shiqiang Ma, Rongbiao Tong
Summary: Oxidative functionalization of indoles is widely used in synthetic chemistry. In this study, we explored the oxidation of indoles using oxone-halide and found that the protecting group on the nitrogen of indoles determines the pathways of oxidation. An electron-withdrawing group on the nitrogen enables C2 halogenation, while C3 halogenation can be achieved without dependence on the protecting group. This environmentally friendly and efficient method allows for the synthesis of 2- or 3-haloindoles without the use of stoichiometric halogenating agents or production of toxic byproducts.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Liyan Song, Yufei Meng, Tongchao Zhao, Lifang Liu, Xiaohong Pan, Binbin Huang, Hongliang Yao, Ran Lin, Rongbiao Tong
Summary: The Hofmann and Curtius rearrangements have been achieved through a green oxidation method using oxone and halide (and NaN3) to generate N-halo amides and acyl azides from amides and aldehydes, respectively. These intermediates further rearrange into stable carbamates or ureas (the Hofmann and Curtius rearrangements) when trapped with alcohols or amines. The method is efficient, environmentally friendly, and produces only non-toxic K2SO4 as a byproduct.
Article
Chemistry, Multidisciplinary
Peilin Tian, Wenkang Ye, Xiayan Zhang, Yi Tong, Pei-Yuan Qian, Rongbiao Tong
Summary: The increase in antibiotic resistance necessitates the development of new antibiotics with novel molecular structures and mechanisms of action. However, the discovery of new antibiotics and their progression into clinical use have been limited in recent decades. The potent anthracimycin antibiotic represents a significant advancement in this field, with its unique structural features and excellent biological activity against various bacteria, including drug-resistant strains. Researchers have successfully achieved the total synthesis of anthracimycin through a 10-step asymmetric synthesis, providing a reliable supply for further studies and allowing the preparation of analogues for structure-activity relationship studies.
Article
Chemistry, Multidisciplinary
Guodong Zhao, Yaxin Wang, Cheng Wang, Haimin Lei, Bingqing Yi, Rongbiao Tong
Summary: Fenton-like chemistry (FLC: CeBr3-H2O2) is utilized for the oxidative desulfurization of thioacetals and thioketals, providing a green, efficient, and chemoselective method for the transformation into carbonyls or alcohols.
