Article
Chemistry, Organic
Yongjin Guo, Hongpeng Bao, Liyuan Chen, Jiarong Shi, Yang Li
Summary: An insertion reaction of benzyne into the Se=O bond has been successfully achieved, leading to the synthesis of two different types of selenium-containing compounds from various substrates.
Article
Chemistry, Organic
Hongpeng Bao, Yongjin Guo, Jiarong Shi, Yang Li
Summary: Two sets of cascade processes were achieved by benzyne insertion into the Se=O bond. The differential factors in these processes are the structures of diaryl selenium oxides and reaction conditions. When diaryl selenium oxides with an ortho weak Sigma- electron-withdrawing group were used, triarylselenonium salts were obtained at room temperature, while ortho-(aryloxy)phenyl phenyl selanes could be produced from diaryl selenium oxides at 100 degrees C.
Article
Chemistry, Multidisciplinary
Eva Kran, Christian Muck-Lichtenfeld, Constantin G. Daniliuc, Armido Studer
Summary: In this study, the reaction of in situ generated arynes with stannylated imines to provide ortho-stannyl-aniline derivatives was reported, with good yields and regioselectivities. The product anilines are valuable starting materials for follow-up chemistry due to the rich chemistry offered by the trimethylstannyl moiety.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Fa-Chuang Liu, Meng-Jie Si, Xin-Ru Shi, Shi-Yi Zhuang, Qun Cai, Yi Liu, An-Xin Wu
Summary: A transition-metal-free formal (4 + 2) cycloaddition for the direct assembly of acridone derivatives has been developed using easily accessible o-aminobenzamides and 2-(trimethylsilyl)aryl triflates. The base plays a crucial role in the controlled synthesis of N-H and N-aryl acridones. Preliminary fluorescence studies show that N-aryl acridones can be used as fluorescent materials with a wide emission range.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Mengyang Shen, Jie Zhao, Yuanshuang Xu, Xinying Zhang, Xuesen Fan
Summary: This novel synthesis method of dihydroquinolinone derivatives involves an unprecedented cascade reaction, which includes the in-situ formation of aryne and its addition with pyrazolidinone, followed by N-N bond cleavage and intramolecular C-C bond formation. Compared to existing methods, this protocol offers advantages such as multiple transformations in one pot, a broad substrate scope, mild reaction conditions, and good tolerance of various functional groups. Additionally, the products obtained from this method demonstrated significant in vitro antiproliferative activity in selected human cancer cell lines.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Wen-Xuan Cao, Lei Zhu, Yiyi He, Run Wang, Ming Liu, Qin Ouyang, Qing Xiao
Summary: The first aryne insertions into the carbon-iodine bond of heteroaryl iodides have been achieved. This novel reaction provides an efficient pathway for the synthesis of valuable building blocks 2-iodoheterobiaryls with excellent regioselectivity by reacting heteroaryl iodides and o-silylaryl triflates. The copper(I) catalyst, which contains a N-heterocyclic carbene (NHC) ligand, is essential for the reaction. Control reactions and DFT calculations suggest that the coordination of copper, acting as a Lewis acid, with nitrogen atoms of heteroaryl iodides mediates the aryne insertions into heteroaryl carbon-iodine bonds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Pei Xie, Yating Zheng, Yuping Luo, Jinyun Luo, Leifang Wu, Zhihua Cai, Lin He
Summary: A facile and efficient method for the synthesis of sulfilimines through multicomponent reaction of arynes, sulfamides, and thiosulfonates was developed. This protocol showed good compatibility with structurally diverse substrates and functional groups, providing the corresponding sulfilimines in high yields. Mechanism studies revealed the key role of sulfenamide in the reaction.
Article
Chemistry, Organic
Yan Jiang, Song Xi, Qi Wang, Lin Fu, Ling He, Zhen Wang, Min Zhang
Summary: A formal two-carbon insertion reaction into β-ketoesters with vinylmetal has been developed for the rapid synthesis of α'-ketoesters. This method features high efficiency, simple operation, and mild conditions without the usage of bases or catalysts.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Jianmin Zhou, Zhi-Yuan Ma, Chantale Shonhe, Su-Hui Ji, Yun-Rui Cai
Summary: The study presents a TEMPO-catalyzed electrosynthetic method for the dehydrogenative cyclocondensation of o-aminophenols to access pharmaceutically valuable 2-aminophenoxazinones. The method is mild, sustainable, and does not require stoichiometric oxidants, providing a new approach for the synthesis of bioactive compounds with improved structural diversity. Mechanistic studies show that electrochemically generated TEMPO+ enables the oxidative radical homo-dimerization of o-aminophenols.
Article
Chemistry, Multidisciplinary
Xavier Abel-Snape, Colton E. Johnson, Bianca Imbriaco, Mark Lautens
Summary: A palladium-catalyzed spirocyclization reaction was reported, which involved the insertion of an oxabicycle into a palladacycle. The reaction proceeded via carbocyclization and a C-H functionalization sequence, and the diastereoselective nature of the insertion was observed. The spirooxindoles produced in the reaction allowed for further transformations and were previously unaccessible.
Article
Chemistry, Organic
Shubhendu S. Karandikar, Bryan E. Metze, Riley A. Roberts, David R. Stuart
Summary: In this study, a one-pot reaction involving diaryliodonium and aryne intermediates is used to substitute the boron group and ortho-hydrogen atom in arylboron compounds. The method demonstrates the versatility of arylboron reagents and arynophiles, and is applied to the formal synthesis of a potential drug candidate.
Article
Chemistry, Organic
Christopher M. Poteat, Vincent N. G. Lindsay
Summary: Sulfonylcyclopropanols are utilized as efficient cyclopropanone equivalents in a formal vinylidene insertion process, leading to the first general synthetic route to enantioenriched alkylidenecyclobutanones. The reaction of an alkenyl-Grignard reagent with N-bromosuccinimide activates the alkenylcyclopropanol for regio- and stereospecific 1,2-migration, resulting in the formation of alkylidenecyclobutanones after elimination. Activation of the intermediate with other electrophiles such as HCl or mCPBA allows for the formation of various chiral cyclobutanones and gamma-lactones through alternative pathways.
Article
Chemistry, Organic
Abhilash Sharma, Hemanta Hazarika, Pranjal Gogoi
Summary: In recent years, o-quinone methides and o-quinone sulfides have been widely recognized as reactive intermediates in the synthesis of diversely functionalized ortho-disubstituted arenes and heterocycles. This synopsis provides a comprehensive overview on the potential applications of these compounds in the one-pot synthesis of ortho-disubstituted arenes and heterocycles via arynes, highlighting their importance in organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Mai Minoshima, Keisuke Uchida, Yu Nakamura, Takamitsu Hosoya, Suguru Yoshida
Summary: An efficient method utilizing triethylsilane and cesium fluoride to generate aryne intermediates from o-iodoaryl triflates has been disclosed, allowing for acylalkylation of arynes using easily accessible precursor. A variety of (hetero)arenes, including fused benzothiazoles, were successfully synthesized from o-iodoaryl triflates due to their good accessibility and diverse transformations of aryne intermediates.
Article
Chemistry, Organic
Ziyi Li, Xinyu Yao, Xin Zhang, Haibo Mei, Jianlin Han
Summary: In this study, the generation of non-stabilized P-ester diazos and their applications in carboxylic acid O-H insertion reactions were reported. This method provides P-acyloxy esters in excellent yield with good tolerance towards various aryl and alkyl-substituted diazos under mild and convenient conditions. Additionally, structural modification of natural products and molecular drugs can be achieved using this reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhilong Chen, Xiaodong Wang
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Zhilong Chen, Jianwei Sun
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2013)
Article
Chemistry, Organic
Lei Ke, Guirong Zhu, Hui Qian, Guangya Xiang, Qin Chen, Zhilong Chen
Article
Multidisciplinary Sciences
Zhuang Ma, Helin Lu, Ke Liao, Zhilong Chen
Article
Chemistry, Multidisciplinary
Lei Ke, Zhilong Chen
COMMUNICATIONS CHEMISTRY
(2020)
Review
Chemistry, Inorganic & Nuclear
Zhilong Chen
Summary: Organohalides are important and useful compounds in organic chemistry, but their traditional halogenation methods generate environmentally unfriendly by-products. Biomimetic halogenation inspired by nature offers a green alternative. This review summarizes the recent progress of biomimetic halogenation using vanadium-dependent haloperoxidase, discussing its challenges, opportunities, and synthetic applications.
COORDINATION CHEMISTRY REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Zhuang Ma, Zhilong Chen
Summary: This study presents a tungstate-catalyzed decarboxylative halogenation of phenolic acids, which can be used to prepare antibiotic bromophene and its analogues. Mechanistic studies suggest that the reaction may proceed through either halogenation-decarboxylation or decarboxylation-halogenation pathway. In addition, chloride ions have an influence on the selectivity of halide in this reaction.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Multidisciplinary Sciences
Helin Lu, Guirong Zhu, Tiange Tang, Zhuang Ma, Qin Chen, Zhilong Chen
