Article
Chemistry, Organic
Alessandra Casnati, Dawid Lichosyt, Bruno Lainer, Lukas Veth, Pawel Dydio
Summary: The research presents a multicatalytic method for converting alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivity. Prochiral allylic alcohols can also be selectively transformed into different stereoisomers of the product.
Article
Chemistry, Organic
Xue Liu, Long Liu, Tianzeng Huang, Jingjing Zhang, Zhi Tang, Chunya Li, Tieqiao Chen
Summary: The trifluoromethylation of benzoic acids using anhydrides as in situ activating reagents allows for a wide range of carboxylic acids to react efficiently, providing a facile method for preparing aryl trifluoromethyl ketones from readily available starting materials.
Article
Chemistry, Organic
Joshua K. Mitchell, Waseem A. Hussain, Ajay H. Bansode, Ryan M. O'Connor, Dan E. Wise, Michael H. Choe, Marvin Parasram
Summary: Here, a protocol for anaerobic oxidation of alcohols, amines, aldehydes, and imines is reported using photoexcited nitroarenes. Mechanistic studies show that photoexcited nitroarenes undergo double hydrogen atom transfer (HAT) steps with alcohols and amines, leading to ketone and imine products. In the presence of aldehydes and imines, successive HAT and oxygen atom transfer (OAT) events occur, yielding carboxylic acids and amides, respectively. The use of a continuous-photoflow setup reduces reaction times.
Article
Chemistry, Multidisciplinary
Martin S. Maier, Andrej Shemet, Dirk Trauner
Summary: The 2'-phosphodiesterase inhibitor A-74528 is a complex type II polyketide with intriguing biosynthesis and unusual biological activity. This study focuses on the synthesis of A-74528, specifically the construction of its carbon skeleton and the installation of its stereocenters. The strategy involves various reactions to establish carbocycles and append the pyrone moiety.
Article
Chemistry, Organic
Keisuke Takahashi, Shunya Kudo, Kiharu Kawamura, Taichi Kusakabe, Shoko Kikkawa, Isao Azumaya, Keisuke Kato
Summary: The proposed structure of mohangic acid C (3) was synthesized through a series of reactions, which selectively introduced specific functional groups and constructed the overall framework of the molecule.
Article
Chemistry, Multidisciplinary
Yu Zhang, Prakash Kumar Sahoo, Peng Ren, Yuman Qin, Robin Cauwenbergh, Philippe Nimmegeers, Gandhi SivaRaman, Steven Van Passel, Andrea Guidetti, Shoubhik Das
Summary: A transition metal-free method has been reported for the selective functionalization of benzylic C(sp(3))-H bonds using alcohols and carboxylic acids as nucleophiles. This straightforward and general approach has provided various benzylic ethers and esters, including twelve pharmaceutically relevant compounds.
CHEMICAL COMMUNICATIONS
(2022)
Correction
Chemistry, Multidisciplinary
Yiju Liao, Alexandria Aspin, Ziming Yang
Summary: This study provides a correction for the paper "Anaerobic oxidation of aldehydes to carboxylic acids under hydrothermal conditions" by Yiju Liao et al. published in RSC Advances. The corrected findings are of significant importance for further developments in this field.
Article
Chemistry, Organic
Rowan I. L. Meador, Robert E. Anderson, John D. Chisholm
Summary: Tertiary benzylic alcohols can react with oxoammonium salts in a tandem elimination/allylic oxidation reaction to synthesize allylic ethers in one step, which can then be cleaved under reductive conditions to yield allylic alcohols.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Nian Li, Yantao Li, Xiaopeng Wu, Chengjian Zhu, Jin Xie
Summary: Deuterated chemicals are indispensable in pharmaceutical engineering, material science, and synthetic chemistry. Radical deuterium-labelling technology has seen rapid growth with the development of radical chemistry, leading to the discovery of diverse, mild, cheap, and efficient strategies for deuterium atom installation. This review summarizes recent achievements of radical deuteration, categorized by reaction types.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Organic
Rui Wang, Pengchao Sun, Weiwei Jin, Yonghong Zhang, Bin Wang, Yu Xia, Fei Xue, Ablimit Abdukader, Chenjiang Liu
Summary: This paper developed two efficient methods for the oxidative cleavage of C-C single bonds of vicinal tertiary diols and discussed their advantages and limitations. The results of the study demonstrate that the organic electrosynthesis method is greener and more efficient.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Applied
Laurent Vanoye, Alain Favre-Reguillon
Summary: This study further investigated the liquid-phase oxidation reaction and demonstrated the pivotal role of acylperoxy radical, while pointing out that the commonly accepted oxidation pathway may be overlooked.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Organic
Felipe C. Demidoff, Guilherme S. Caleffi, Marcella Figueiredo, Paulo R. R. Costa
Summary: The article describes the one-pot C=C/C=O reduction of chalcones using a oxo-tethered-Ru(II) precatalyst, showing good yields and enantiomeric purities. The results indicate that the enones are first reduced to dihydrochalcones and then converted into 1,3-diarylpropan-1-ols. The study also evaluates the effects of different groups at various positions on the aromatic ring and highlights the tolerance of the 2-OH group.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jayabrata Das, Wajid Ali, Animesh Ghosh, Tanay Pal, Astam Mandal, Chitrala Teja, Suparna Dutta, Rajagopal Pothikumar, Haibo Ge, Xinglong Zhang, Debabrata Maiti
Summary: Transition metal catalysis plays a crucial role in activating unreactive C-H bonds. However, selectively activating distal aliphatic C-H bonds without directing templates is highly challenging. In this study, we demonstrated the activation of a methylene C-H bond in the presence of methyl C-H bonds to form unsaturated bicyclic lactones. This method enables the reversal of general selectivity in aliphatic C-H bond activation and simplifies the synthesis of important bicyclic lactones found in natural products and pharmaceuticals.
Article
Chemistry, Organic
Donghui Guo, Qiupeng Peng, Bei Zhang, Jian Wang
Summary: The novel method described in this report allows for the atroposelective generation of axially chiral amino esters using hemiaminals formed in situ, with a wide substrate scope, good functional group tolerance, and rapid assembly of axially chiral amino esters with high enantioselectivities in good to high yields.
Article
Chemistry, Multidisciplinary
Du Chen, Liangxuan Xu, Yi Yu, Qinliang Mo, Xiaotian Qi, Chao Liu
Summary: Developing new and efficient methods for the controlled conversion of carboxylic acids to aldehydes is crucial. In this study, a rapid, modular and scalable method using pinacolborane at ambient temperature was developed. The reduction of acylpyridinium by HBpin enables the direct synthesis of aldehydes from carboxylic acids, with lower activation energy compared to the product aldehyde. The synthetic advantage of this protocol is demonstrated through scalable synthesis of aldehyde via continuous flow process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Thomas Siemon, Simon Steinhauer, Mathias Christmann
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Multidisciplinary
Caroline Apel, Sven Soeren Hartmann, Dieter Lentz, Mathias Christmann
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Organic
Benjamin F. Hohlfeld, Keith J. Flanagan, Nora Kulak, Mathias O. Senge, Mathias Christmann, Arno Wiehe
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Biochemistry & Molecular Biology
Marc-Andre Kasper, Marcus Gerlach, AnseIm F. L. Schneider, Christiane Groneberg, Philipp Ochtrop, Stefanie Boldt, Dominik Schumacher, Jonas Helma, Heinrich Leonhardel, Mathias Christmann, Christian P. R. Hackenberger
Article
Chemistry, Multidisciplinary
Thomas Siemon, Zhangqian Wang, Guangkai Bian, Tobias Seitz, Ziling Ye, Yan Lu, Shu Cheng, Yunkun Ding, Yanglei Huang, Zixin Deng, Tiangang Liu, Mathias Christmann
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Organic
Florian Bartels, Manuela Weber, Mathias Christmann
Article
Chemistry, Organic
Johannes Schwan, Merlin Kleoff, Philipp Heretsch, Mathias Christmann
Article
Chemistry, Organic
Merlin Kleoff, Johannes Schwan, Lisa Boeser, Bence Hartmayer, Mathias Christmann, Biprajit Sarkar, Philipp Heretsch
Article
Chemistry, Multidisciplinary
Benjamin Schmidt, Sebastian Ponath, Johannes Hannemann, Patrick Vossnacker, Karsten Sonnenberg, Mathias Christmann, Sebastian Riedel
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Organic
Merlin Kleoff, Johannes Schwan, Mathias Christmann, Philipp Heretsch
Summary: A modular flow platform was designed for natural product synthesis, utilizing interchangeable 3D-printed components for flexible reaction setups. By adopting liquid- to gas-driven flow, reagent and solvent waste is minimized, leading to a sustainable profile. Schlenk-in-flow techniques were developed for safe handling of sensitive reagents, enabling reproducible transformations in natural product synthesis.
Review
Chemistry, Organic
Caroline Apel, Mathias Christmann
Summary: Organocatalytic synthesis of cyclopropanes is a well-studied transformation that has the potential to combine with the implementation of the cyclopropyl motif into organocatalysts and the activation of cyclopropanes. This combination can benefit from the unique reactivity of cyclopropanes.
Article
Chemistry, Multidisciplinary
Guoli He, Benjamin List, Mathias Christmann
Summary: An complementary dual carbonyl activation strategy has been developed for the synthesis of polycyclic alkaloids, resulting in successful applications for the synthesis of tetracyclic, pentacyclic, and octacyclic alkaloids. The synthesis features protecting-group-free assembly and an asymmetric disulfonimide-catalyzed cyclization. Additionally, formal syntheses of various alkaloids have been achieved, including a concise synthesis of berberine alkaloid ilicifoline B.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Stefan Leisering, Alexandros Mavroskoufis, Patrick Vossnacker, Reinhold Zimmer, Mathias Christmann
Summary: A protecting-group-free synthesis of two endoperoxide natural products, plakortolide E and plakortolide I, was achieved by combining chemoselective bond-forming reactions and one-pot operations. Key steps included vanadium-mediated epoxidation, iron-catalyzed allylic substitution, and cobalt-induced endoperoxide formation, resulting in an overall efficient synthesis.
Article
Chemistry, Organic
Stefan Leisering, Sebastian Ponath, Kamar Shakeri, Alexandros Mavroskoufis, Merlin Kleoff, Patrick Vossnacker, Simon Steinhauer, Manuela Weber, Mathias Christmann
Summary: In this study, a synthesis of 3-epi-hypatulin B, a highly oxygenated and densely functionalized bicyclic scaffold, was reported. The carbon skeleton was prepared through functionalization of a cyclopentanone and an intramolecular Mukaiyama aldol reaction. Notably, a late-stage photo-oxidation of a methoxyallene was employed to provide an ester group. The translation of the batch process into a flow protocol successfully solved the problems encountered. This synthesis highlights the importance of flow chemistry in enabling challenging late-stage transformations in natural product synthesis.
Article
Chemistry, Organic
Marcel Gausmann, Nadine Kreidt, Mathias Christmann
Summary: An electrochemical oxidation of amino acid carbamates (R1 = Boc, Cbz) mediated by NaCl was conducted, resulting in the production of alpha-methoxylated alpha-amino acids. Valuable dehydroamino acid derivatives were obtained through subsequent acid-catalyzed elimination. The simplicity of our setup using graphite-electrodes was demonstrated by the preparation of N-Boc-Delta Ala-OMe on a decagram scale.
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)