Article
Chemistry, Applied
Shuang Wu, Yiyun Chen
Summary: In this study, we demonstrate the alpha-C-H acyloxylation of sulfides and disulfides using hypervalent iodine(III) reagents and photoredox catalysis. Methoxylbenziodoxole derivatives act as hydrogen atom transfer agents, mild oxidants, and acyloxylation sources in the reaction. External nucleophiles can also be introduced to the alpha-C-H of sulfides. This reaction is applicable to various aryl and alkyl sulfides, including methionine peptide derivatives. Disulfides can be used for the first time with excellent chemoselectivity and functional group compatibility.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Nagarajan Ramkumar, Larisa Baumane, Dzintars Zacs, Janis Veliks
Summary: A simple process for the oxy-monofluoromethylation of alkenes is presented. The use of visible-light copper(I) photoredox catalysis, in combination with an easily accessible iodine(III) reagent containing monofluoroacetoxy ligands, enables the synthesis of gamma-fluoro-acetates from various olefinic substrates under mild conditions. The study also demonstrates its applications in late-stage diversification of complex molecules, amino acids, and the synthesis of fluoromethylated heterocycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Sabrina Giofre, Letizia Molteni, Donatella Nava, Leonardo Lo Presti, Egle Maria Beccalli
Summary: Excellent enantio- and diastereoselectivity can be achieved in the oxidative Pd-catalyzed dioxygenation of (aza-)alkenols by using specific chiral ligands and hypervalent-iodine compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Chenyang Wang, Peng Shi, Carsten Bolm
Summary: In this study, dichloro- and dibromomethane were utilized as halogen sources to convert NH-sulfoximines to N-halo derivatives, using an in situ formed sulfoximidoyl-containing hypervalent iodine reagent under visible light. The reactions were carried out in air without the need for catalysts or additives, and the products were obtained in good to excellent yields.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Javier Ceballos, Elija Grinhagena, Gontran Sangouard, Christian Heinis, Jerome Waser
Summary: The study introduces a novel method for preparing stapled peptides using bis-functional hypervalent iodine reagents for two-component cysteine-cysteine and cysteine-lysine stapling. This method does not require pre-functionalization or metal catalysis, and the products are stable for purification and isolation, with post-stapling modifications possible through various methods.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Mengning Wang, Cheng Chen, Mengtao Ma, Binlin Zhao, Zhuangzhi Shi
Summary: A general, scalable, and convenient photochemical process is reported for the synthesis of various distal oxygenated nitriles from less-strained ketoxime esters. This method allows for one-step introductions of ether and cyano groups, eliminating the need for toxic cyanide reagents. The reaction is applicable to a wide range of cycloketoxime esters and linear ketoxime esters, providing structurally diverse ring-opening products under simple and mild conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Lachlan Barwise, Jason D. Bennetts, Keith F. White, Jason L. Dutton
Summary: The synthesis and crystallographic characterization of NO2-C6H4-I(NTf2)(2) (NTf2 = bistriflimide) are reported. Experimental results demonstrate that this compound is capable of performing oxidation reactions that ArI(OTf)2 is unable to. Theoretical analysis indicates that Ar-I(NTf2)(2) is the most oxidizing compound among the known ArIL2 class of compounds, and it may also be the most oxidizing compound among the practically possible compounds in this class.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Abhaya Kumar Mishra, Romain Tessier, Durga Prasad Hari, Jerome Waser
Summary: In this study, functionalization of cysteine residues with lipophilic alkynes using amphiphilic ethynylbenziodoxolone reagents (EBXs) was successfully achieved under physiological conditions without the need for organic co-solvent or removal of oxygen. The transformation led to a significant increase of peptide lipophilicity and worked for various thiol-containing compounds and peptides of different lengths. His(6)-Cys-Ubiquitin was also alkynylated under these conditions, demonstrating the versatility of this method.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Lotte Stockhammer, Johannes Schoergenhumer, Christopher Mairhofer, Mario Waser
Summary: This study introduces an unprecedented strategy for the asymmetric alpha-chlorination of beta-keto esters using simple Cinchona alkaloid catalysts and hypervalent iodine-based Cl-transfer reagents. The Cinchona species was found to act as a nucleophilic catalyst, generating a chiral electrophilic Cl-transfer reagent in situ, leading to good yields and enantioselectivities under operationally simple conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Ni Xiong, Yang Li, Rong Zeng
Summary: We present a dual catalytic strategy for the functionalization of aliphatic carboxylic acids using photoinduced iron/copper catalysts. The photoinduced ligand-to-iron charge transfer process generates an unstabilized alkyl radical, which is then utilized by the copper catalyst for coupling reactions to form C-N or C-C bonds. This system enables efficient conversion of a wide range of aliphatic carboxylic acids and has potential applications in drug discovery.
Article
Chemistry, Physical
Ni Xiong, Yang Li, Rong Zeng
Summary: We have developed a photoinduced iron/copper dual-catalytic strategy for the radical decarboxylation functionalization of aliphatic carboxylic acids. By merging iron-catalyzed decarboxylation with copper catalysis, this system allows efficient conversion of a wide range of aliphatic carboxylic acids for various reactions. The strategy has applications in compound library synthesis and the discovery of pharmaceutical agents.
Article
Chemistry, Organic
Kui Lu, Lingyu Lei, Qijun Wei, Ting Zhou, Xiaodong Jia, Quan Li, Xia Zhao
Summary: This study reports the visible light-induced radical aryldifluoromethylation of N-arylacrylamides using [bis(difluoroacetoxy)iodo]benzene as a difluoromethylation reagent for the first time. The use of inexpensive and readily accessible reagents and mild reaction conditions make this method an alternative and practical strategy for the synthesis of difluoromethyl substituted oxindoles.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Michael Schaefer, Timo Stuenkel, Constantin G. Daniliuc, Ryan Gilmour
Summary: The regio- and enantioselective intermolecular vicinal fluoroamination of alpha-trifluoromethyl styrenes has been achieved through enantioselective I-I/I-III catalysis, providing facile access to tertiary benzylic stereocenters bearing both CF3 and F groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Raphael Simonet-Davin, Jerome Waser
Summary: In this short review, applications of hypervalent iodine reagents for the azidation of organic compounds were described, with a focus on stable cyclic reagents. Important advances in the azidation of C-H bonds, alkenes, and other transformations were highlighted through selected key reports.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Inorganic & Nuclear
Huai-Ming Li, Guan-Dong Li, Jun-Yu Li, Teng Zhang
Summary: An iodine-functionalized metal-organic framework (MOF), UiO-68-I, was synthesized and showed good catalytic activity for dibromination of alkenes and alkynes. Its low catalyst loading of 1% allows for efficient recycling and recovery. Mechanistic studies suggest that UiO-68-I may accelerate the reaction by triggering the formation of molecular bromine through a radical intermediate. The activity and stability of UiO-68-I surpasses previous reports on organoiodine catalysts, highlighting the potential of iodine-functionalized MOFs as recyclable heterogeneous hypervalent iodine reagents or catalysts.
INORGANIC CHEMISTRY COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Ya-Fang Chen, Rui-Yue Ma, Lu-Nan Zhou, Zhenting Du, Tao Zhang
Article
Chemistry, Multidisciplinary
Jing Zhou, Maximilian W. Kuntze-Fechner, Ruediger Bertermann, Ursula S. D. Paul, Johannes H. J. Berthel, Alexandra Friedrich, Zhenting Du, Todd B. Marder, Udo Radius
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2016)
Article
Chemistry, Multidisciplinary
Rui-Yue Ma, Ya-Fang Chen, Jun-Ru Wang, Zhen-Ting Du
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2018)
Review
Chemistry, Multidisciplinary
Yin Wang, Congyang Wang
CHINESE CHEMICAL LETTERS
(2018)
Article
Biochemistry & Molecular Biology
Zhi-Feng Sun, Tao Zhang, Jinyang Liu, Zhen-Ting Du, Huaiji Zheng
Article
Biochemistry & Molecular Biology
Hong-Li Zhang, Zhi-Feng Sun, Lu-Nan Zhou, Lu Liu, Tao Zhang, Zhen-Ting Du
Article
Chemistry, Multidisciplinary
Yin Wang, Yunhui Yang, Congyang Wang
CHINESE JOURNAL OF CHEMISTRY
(2019)
Article
Engineering, Chemical
Haolong Wang, Tengfei Cui, Jixue Sui, Pavle Mocilac, Yin Wang, Zhijun Guo
Summary: The asymmetric alkyl-substituted DAPhens showed higher affinity for UO22+ compared to symmetric analogues, likely due to decreased steric hindrance from methyl in the terminal groups. This was confirmed through the crystal and molecular structure of the solid-state complex, supporting their potential application as selective ligands.
SEPARATION AND PURIFICATION TECHNOLOGY
(2022)
Article
Biochemistry & Molecular Biology
Ruibo Wang, Ruiting Kang, Xuan Yang, Yu Cheng, Hongjin Bai, Zhenting Du
Summary: A series of benzoxazole derivatives were synthesized and evaluated for their antifungal activity. Most of the compounds showed moderate antifungal activities, with three candidates exhibiting the strongest activity.
Article
Chemistry, Medicinal
Guo-Guo He, Si-Fan Liu, Bao-Qi Rao, Hong-Jin Bai, Zhen-Ting Du
Summary: The asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth, has been efficiently achieved, with a key chiral intermediate obtained in large quantities from the steroid industry. Selective masking and conversion into a phosphonium salt derivative were used to construct the carbon skeleton, with the target molecule synthesized in 8 linear steps and a 42% yield. The key characteristic of this synthesis lies in its chiral-pool strategy.
NATURAL PRODUCT COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Chun-Ting He, Xiao-Li Han, Yan-Xue Zhang, Zhen-Ting Du, Chang-Mei Si, Bang-Guo Wei
Summary: An efficient method has been developed to access functionalized (2,3-dihydroisoxazol-4-yl) ketones by reacting nitrones with ynones or terminal ynones in a one-pot fashion, resulting in moderate to good yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Lei Zhang, Yin Wang, Yunhui Yang, Ping Zhang, Congyang Wang
ORGANIC CHEMISTRY FRONTIERS
(2020)
Article
Chemistry, Multidisciplinary
Tao Zhang, Jun Jiang, Lin Yao, Huiling Geng, Xumu Zhang
CHEMICAL COMMUNICATIONS
(2017)
Article
Chemistry, Medicinal
Liang-Zhu Huang, Rui-Yue Ma, Lu-Nan Zhou, Zhen-Ting Du, Tao Zhang
NATURAL PRODUCT COMMUNICATIONS
(2017)
Article
Chemistry, Multidisciplinary
Zhi-Feng Sun, Lu-Nan Zhou, Tao Zhang, Zhen-Ting Du
CHINESE CHEMICAL LETTERS
(2017)
