Article
Chemistry, Organic
Tania, Andrew Molino, Lachlan Sharp-Bucknall, David J. D. Wilson, Jason L. Dutton
Summary: PhIBr2, a substance with low stability, has been recently shown to be formed in situ by reacting PIFA with TMSBr, and has demonstrated efficacy in aryl brominations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Liangkun Pan, Long Zheng, Ye Chen, Zhihai Ke, Ying-Yeung Yeung
Summary: A mechanochemical method using hypervalent iodine reagents has been developed for the functionalization of olefins, enabling the synthesis of 1,3-dioxygenated compounds. Under similar reaction conditions with the addition of molecular iodine, 1,4-iodoalcohols can also be synthesized. These valuable products are difficult to achieve using traditional solution-phase methods. Mechanistic study suggests that the hypervalent iodine reagent may dimerize at the solid state and trigger the 1,3- and 1,4-difunctionalization reactions in an intermolecular cascade manner.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jiaqi Cao, Youcai Ma, Liangzhen Hu, Wen Xia, Xiaohui Zhang, Yan Xiong
Summary: This study presents a novel dearomative spirolactonization/polyhalogenation of phenols using hypervalent iodine as both an oxidant and chlorine source, in the presence of a base or using NBS without additives. Halide participations are crucial in the cascade reaction, leading to the rapid construction of C-halogen and C=O bonds under mild conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Raphael Robidas, Claude Y. Legault
Summary: Hypervalent iodine reagents are powerful tools in contemporary organic synthesis, particularly in oxidative transformations. Cyclic haloiodanes are versatile reagents that can promote various reactions with unique reactivity, expanding the scope of electrophilic halogenation chemistry.
HELVETICA CHIMICA ACTA
(2021)
Article
Chemistry, Multidisciplinary
Lachlan Sharp-Bucknall, Tania, Jason L. Dutton
Summary: This article describes the synthesis and structural characterization of NO2-PhI(OTf)(2), a compound that is resistant to decomposition and has higher reactivity than previously misidentified PhI(OTf)(OAc), confirming the non-existence of PhI(OTf)(2) as an intermediate in oxidation reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Loic Habert, Kevin Cariou
Summary: In this study, the aerobic iodoarene catalysis was achieved by using a pyrylium photocatalyst under blue light irradiation, allowing for the use of low catalytic loading of both catalysts under very mild operating conditions. This unprecedented dual organocatalytic system provides a powerful and efficient methodology for spiro-cyclization of amides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Inorganic & Nuclear
Lachlan Sharp-Bucknall, Marcus Sceney, Keith F. F. White, Jason L. L. Dutton
Summary: This article describes the synthesis, reactivity, and comprehensive characterization of two new compounds, ArI(OTf)(X), which were previously only considered as reactive intermediates where X = Cl, F, and their different reactivities with aryl substrates. It also introduces a new catalytic system for electrophilic chlorination of deactivated arenes using Cl-2 as the chlorine source and ArI/HOTf as the catalyst.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Multidisciplinary
Huaiyuan Zhang, Thomas Wirth
Summary: Xanthene derivatives derived from BINOL have wide applications in various fields such as medicine, fluorescent probes, dyes, and food additives. Researchers have developed synthetic methods for preparing the oxidized products of BINOL using different methods. One-pot reactions of BINOLs, reagents, and nucleophiles have also been investigated, resulting in high-yielding products.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Physical
Junjie Yang, Yung-Yin Chan, Weida Feng, Ying-Lung Steve Tse, Ying-Yeung Yeung
Summary: Electrophilic halogenation reactions are commonly used in various areas. N-Haloamides are frequently employed as halogen sources, but their activation is often achieved with Lewis basic chalcogens as catalysts. However, the resulting intermediate is sensitive to moisture and nucleophiles, limiting its compatibility in some reactions. This study introduces a highly efficient catalytic halogenation protocol using phenyl selenium with ortho-substituted carboxylic acid as the catalyst, which demonstrates improved stability and applicability in various electrophilic functionalization reactions.
Review
Biochemistry & Molecular Biology
Samata E. Shetgaonkar, Subhiksha Jothish, Toshifumi Dohi, Fateh V. Singh
Summary: The chemistry of hypervalent iodine reagents has become valuable due to their reactivity under mild reaction conditions and resemblance to transition metals. These environmentally friendly reagents are suitable for Green Chemistry. Iodine(V) reagents, such as IBX and DMP, have been used as oxidants in organic synthesis either stoichiometrically or catalytically. This review article describes various oxidation reactions induced by iodine(V) reagents reported in the past decade.
Article
Chemistry, Multidisciplinary
Lei Zhang, Wangzhen Bao, Yuchen Liang, Wenjing Pan, Dongyang Li, Lichun Kong, Zhi-Xiang Wang, Bo Peng
Summary: This study demonstrates the reversal of stereoselectivity in MBH-type [3,3]-rearrangement by using a new pair of rearrangement partners, leading to the synthesis of different types of alpha-aryl alpha,beta-unsaturated carbonyl derivatives. Mechanistic studies provide insights into the reaction pathway and the opposite stereoselectivities observed.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Maxime Denis, Samuel Blais, Sylvain Canesi
Summary: A stereoselective synthesis of isolycoricidine, a natural product belonging to the Amaryllidaceae alkaloids family, was achieved. The study also conducted a synthetic investigation on the main core of lycoricidine, resulting in the formation of analogues and a diastereomer of dihydrolycoricidine. The research utilized various strategies including oxidative phenol dearomatization, stereoselective Heck process, selective dihydroxylation, stereoselective reductions, and oxidative retro-Michael procedure as an amine-deprotecting group strategy. In addition, the study highlighted the usefulness of hypervalent iodines in total synthesis of natural products.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Organic
Irina A. Mironova, Stefan F. Kirsch, Viktor V. Zhdankin, Akira Yoshimura, Mekhman S. Yusubov
Summary: This review summarizes recent approaches to the direct synthesis of organic azides using hypervalent iodine reagents. The first part discusses the use of unstable azidoiodinanes generated in situ, while the second part focuses on the application of stable azidobenziodoxoles as azidating reagents. The use of azidobenziodoxoles allows for selective direct azidation of specific bonds under mild reaction conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Ravi Kumar, Fateh V. Singh, Naoko Takenaga, Toshifumi Dohi
Summary: The review focuses on asymmetric oxidative dearomatization reactions involving hypervalent iodine compounds, summarizing asymmetric intra- and intermolecular dearomatization reactions using chiral hypervalent iodine reagents/catalysts as well as hypervalent iodine-mediated dearomatization reactions followed by desymmetrization.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Xuan Cheng, Quan Yin, Yu-Xuan Jiang, Ling-Feng Jiang, Si-Yuan Li, Yi-Fei Cheng, Xin-Chang Sun, Lujun Peng, Cheng Zhong, Qing-Hai Deng
Summary: In this study, bench-stable and highly reactive noncyclic hypervalent iodine nitrooxylating reagents were developed for efficient access to organic nitrates. These reagents showed excellent performance in regioselective nitrooxylation of cyclopropyl silyl ethers and catalyst-free nitrooxylation of enolizable C-H bonds. The protocol provides a practical and direct approach to various organic nitrates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Biochemistry & Molecular Biology
Catharina J. Seel, Tanja Gulder
Editorial Material
Multidisciplinary Sciences
Aaron Gutierrez Collar, Tanja Gulder
Article
Biochemistry & Molecular Biology
Daniel Stierli, Martin Eberle, Clemens Lamberth, Olivier Jacob, Dirk Balmer, Tanja Gulder
Summary: This paper presents the pathway to the discovery of a previously unknown subclass of Carboxylic Acid Amide (CAA) fungicides, which is the first of its kind without a carboxamide function. The synthesis routes, structure-activity relationship studies, and resistance profile of this novel family of fungicides are also discussed in detail.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Madleen Busse, Jaroslaw P. Marciniszyn, Simone Ferstl, Melanie A. Kimm, Franz Pfeiffer, Tanja Gulder
Summary: Conventional histology is based on evaluating 2D slices of a 3D biopsy, while 3D X-ray histology overcomes this limitation by enhancing soft tissue X-ray contrast through tissue staining before CT imaging. The ideal X-ray contrast agent, dibromo fluorescein barium salt, allows for 3D imaging and subsequent complementing counterstaining using standard histological techniques.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Gabriel M. Kiefl, Tanja Gulder
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Anish Das, Chris Weise, Matthias Polack, Raphael D. Urban, Benjamin Krafft, Sadat Hasan, Hannes Westphal, Rico Warias, Simon Schmidt, Tanja Gulder, Detlev Belder
Summary: This study presents an approach for the online coupling of digital microfluidics with mass spectrometry. The technique uses a chip-integrated microspray hole to analyze a portion of a sample droplet by mass spectrometry. The method eliminates the need for chip disassembly or capillary emitters, allowing the advantages of digital microfluidics to be retained during mass spectrometry analysis. The developed coupling technique has been successfully applied to various applications, including organic synthesis and protein analysis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Biochemistry & Molecular Biology
Paul M. D'Agostino, Catharina J. Seel, Xiaoqi Ji, Tanja Gulder, Tobias A. M. Gulder
Summary: This study elucidates the biosynthetic process of furanolide assembly, providing insights into the function and mechanism of key enzymes. It expands the biocatalytic toolbox for gamma-butyrolactone formation and lays the foundation for targeted discovery and enzymatic synthesis of furanolides.
NATURE CHEMICAL BIOLOGY
(2022)
Article
Biochemistry & Molecular Biology
Jelena Lazic, Sanja Skaro Bogojevic, Sandra Vojnovic, Ivana Aleksic, Dusan Milivojevic, Martin Kretzschmar, Tanja Gulder, Milos Petkovic, Jasmina Nikodinovic-Runic
Summary: Prodigiosins are bacterial secondary metabolites with remarkable biological activities and color. In this study, prodigiosin (PG) was successfully produced, purified, and characterized from Serratia marcescens ATCC 27117 strain. Novel brominated derivatives of PG were also synthesized. PG and its brominated derivatives showed potential in cancer treatment but had low selectivity against healthy cells. The brominated derivatives exhibited improved toxicity compared to PG, which is a significant finding for further optimization of bacterial prodigiosins.
Article
Chemistry, Organic
Martin Kretzschmar, Tanja Gulder
Summary: In this article, we present a generally applicable umpolung method for the alpha-functionalization of ketones, using cyclic hypervalent fluoro-iodane as the key reagent. The reaction not only enables various alkene functionalizations, but also leads to the formation of alpha-functionalized ketones as minor side products. Further investigation revealed a directed umpolung of pyridyl ketones by the fluoro-iodane, which was facilitated by unexpected non-covalent interactions between the nucleophile, substrate, and iodane.
Review
Biochemistry & Molecular Biology
Joerg Matysik, Luca Gerhards, Tobias Theiss, Lisa Timmermann, Patrick Kurle-Tucholski, Guzel Musabirova, Ruonan Qin, Frank Ortmann, Ilia A. Solov'yov, Tanja Gulder
Summary: This review summarizes the phenomenon of nuclear hyperpolarization occurring in chemical reactions, known as CIDNP or photo-CIDNP if driven by light. It occurs in both liquid and solid-state, often involving electron transfer systems with flavins as electron acceptors. The article explains the properties of flavins, their occurrence in spin-correlated radical pairs (SCRPs), and the potential involvement of flavin-carrying SCRPs in animal magneto-reception at Earth's magnetic field.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Multidisciplinary Sciences
Andreas M. M. Arnold, Philipp Dullinger, Aniruddha Biswas, Christian Jandl, Dominik Horinek, Tanja Gulder
Summary: The authors report the synthesis of (poly)cyclic carbon frameworks using in-situ formed fluorinated-alcohol-amine supramolecular clusters that mimic terpene cyclases. Terpene cyclases are highly efficient and selective catalysts in natural product synthesis. The supramolecular clusters act as artificial cyclases, triggering enzyme-like reactivity and selectivity by controlling substrate conformation in solution.
NATURE COMMUNICATIONS
(2023)
News Item
Chemistry, Multidisciplinary
Rachel C. Epplin, Tanja Gulder
Summary: Fluorination strategies are crucial for pharmaceutical synthesis. Iodine catalysis has been widely used for introducing gem-difluoro groups, but it is limited to styrenes. The hypervalent iodane-catalysed difluorination of enynes now provides access to diverse homopropargylic difluorides.
Article
Chemistry, Multidisciplinary
Julia Binder, Aniruddha Biswas, Tanja Gulder
Summary: In this study, a novel chlorination-induced polyene cyclization method is proposed, utilizing HFIP-chloroiodane networks to mimic terpene cyclases. Various different alkenes were converted with high selectivities (up to d.r. > 95:5). The cyclization platform was also successfully extended to structurally challenging terpenes and terpenoid carbon frameworks.
Meeting Abstract
Chemistry, Multidisciplinary
Andreas Arnold, Alexander Pothig, Tanja Gulder
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2018)
