Article
Chemistry, Multidisciplinary
Daniel Richter, Edgars Lakis, Jorn Piel
Summary: The tetrazine ligation is a versatile and fast reaction commonly used for bioorthogonal modifications. However, the incorporation of dienophiles in biomolecules has been limited by the need for externally added reagents. This study introduces a novel strategy, called TyrEx cycloaddition, which enables autonomous dienophile generation in bacteria. This technique has been successfully applied for the labeling of proteins and holds potential for various applications.
Article
Chemistry, Multidisciplinary
Luca De Angelis, Graham C. Haug, Gildardo Rivera, Soumen Biswas, Ammar Al-Sayyed, Hadi Arman, Oleg Larionov, Michael P. Doyle
Summary: One important reaction of 1,2,3-triazines is the inverse electron demand Diels-Alder (IEDDA) cycloaddition with a dienophile, which proceeds through nucleophilic addition to the triazine followed by N-2 loss and cyclization. Previous studies have not provided a comprehensive understanding of the site of nucleophilic addition on the triazine. This study investigated the C-, N-, H-, O-, and S-nucleophilic additions on 1,2,3-triazine and 1,2,3-triazine-1-oxide frameworks and revealed the differentiation of addition at the 4- and 6-positions. Computational studies further examined the factors influencing the outcomes of these reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Batoul Rkein, Romain Coffinier, Marian Powderly, Maxime Manneveau, Morgane Sanselme, Muriel Durandetti, Muriel Sebban, Ghanem Hamdoun, Hassan Oulyadi, David Harrowven, Julien Legros, Isabelle Chataigner
Summary: This article investigates the reaction of nitroarenes with silyloxydienes under high pressure and demonstrates the successful dearomatizing [4+2] cycloadditions at room temperature, resulting in highly functionalized compounds with tetrasubstituted carbon centers.
CHEMICAL COMMUNICATIONS
(2022)
Article
Polymer Science
Merlina Thiessen, Volker Abetz
Summary: This study focuses on the reversibility of crosslink formation in copolymers containing furfuryl and maleimide groups based on Diels-Alder reaction. It was found that the reversibility of crosslinking is strongly influenced by the glass transition temperature of the system.
Article
Biochemistry & Molecular Biology
Chia-Jui Lee, Manickavasakam Ramasamy, Hsuan-Hao Kuan, Chien-Huang Wu, Chein-Chung Lee, Jinq-Chyi Lee, Kak-Shan Shia
Summary: Using a Diels-Alder approach with various alpha,beta-unsaturated 2-carbomethoxy-4,4-dimethyl-1-tetralones as dienophiles, polycyclic adducts were synthesized efficiently in yields ranging from 74% to 99% in the presence of Lewis acid (e.g., SnCl4). This establishes a synthetic platform for creating a focused library of aromatic polyketide-like compounds for screening potential natural and non-natural antimicrobial agents.
Article
Chemistry, Organic
Haruka Morizumi, Kaii Nakayama, Yoshikazu Kitano, Yohei Okada
Summary: In this study, a possible radical cation Diels-Alder reaction using an enol ether as an electron-rich dienophile was revealed through a rationally designed redox tag strategy. The reaction was driven by both intermolecular and intramolecular electron transfers, which were effectively achieved through electrochemical and TiO2 photochemical approaches.
Article
Chemistry, Organic
Yunrong Chen, Xueqian Ye, Faqian He, Xiaoyu Yang
Summary: An efficient radical conjugate addition/enantioselective protonation process was developed for N-aryl glycines and alkenyl oxazolines enabled by cooperative photoredox catalysis and chiral phosphoric acid catalysis, leading to a series of chiral oxazolines with high enantioselectivities. The facile transformations of the chiral oxazoline products into enantioenriched lactams and gamma-amino esters with alpha-stereocenters demonstrate the value of this method.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Polymer Science
Aaron Perez, Gerard Lligadas, Juan Carlos Ronda, Marina Galia, Virginia Cadiz
Summary: Block copolymers containing poly(trimethylene carbonate) (PTMC) middle block and poly(furfuryl methacrylate) PFMA end blocks were synthesized and their thermal and mechanical properties were studied. Crosslinking via Diels-Alder (DA) reaction and thermoreversibility properties of the crosslinked polymer were investigated.
EUROPEAN POLYMER JOURNAL
(2022)
Article
Chemistry, Organic
Ilya Nechaev, Georgij Cherkaev, Nikolay Boev, Pavel N. Solyev
Summary: A new three-component reaction has been discovered, which can synthesize compounds with specific structure under mild conditions and high functional group tolerance, selectively functionalizing pyridines, and the reaction mechanism involves a rare [4+2] cycloaddition step.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Annie R. Hooper, Alexander S. Burns
Summary: In this study, a masking strategy using acrylamides is reported, allowing the introduction of masked functionality early in a synthetic route and specific thermal deprotection. The stability of acrylamide adducts is influenced by solvent and structural factors, as determined through kinetic studies. This protection strategy improves the yield of base-promoted reactions.
ACS MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Organic
Maninderjeet Kaur Mann, Rashmi Sharma, Pooja Chawla, Rupesh Kumar, Gaurav Bhargava
Summary: This reported work describes the stereo-, regio-, and pi-facial selective synthesis of hetero-Diels-Alder (H-DA) cycloadducts with diazene derivatives, specifically di-isopropyldiazocarboxylate and diethylazodicarboxylate, and cis/trans-3-butadienyl-beta-lactams. The H-DA reactions resulted in the formation of beta-lactam tethered-3,6-dihydro-pyridazines in good yields.
POLYCYCLIC AROMATIC COMPOUNDS
(2023)
Article
Chemistry, Organic
Henning Hopf, Michael S. Sherburn
Summary: Allenes have traditionally played a minor role in Diels-Alder cycloadditions, but their importance has grown with their increased availability and unique stereochemical features. This review provides a comprehensive overview of allenes in Diels-Alder processes, covering their application in dienes, dienophiles, and cycloadducts, discussing both inter- and intramolecular cycloadditions, and describing the stereochemical aspects of the addition process. Emerging areas such as the use of allenic components in dehydro-Diels-Alder processes and dendralenic allenes for rapid generation of molecular complexity are also addressed, along with preparatively useful methods for allenic precursor synthesis.
SYNTHESIS-STUTTGART
(2022)
Article
Nanoscience & Nanotechnology
Damian Jedrzejowski, Michal Ryndak, Jakub J. Zakrzewski, Maciej Hodorowicz, Szymon Chorazy, Dariusz Matoga
Summary: In this study, the authors demonstrate the solvent-free mechanochemical transformation of metal-organic frameworks (MOFs) for the functionalization of their pores. The modified MOFs with pendant hydroxyl groups show changes in network rigidity, luminescent properties, and adsorption capacity for various gases and liquids. The authors also identify a flexible MOF with luminescent humidity sensing capabilities and explain the influence of water on its luminescence using the excited-state intramolecular proton transfer (ESIPT) model. Overall, this work provides guidance for designing and tuning MOFs for luminescence-based detection.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Review
Chemistry, Organic
Fedor I. Zubkov
Summary: This review summarizes the literature on intramolecular Diels-Alder reactions of vinylarenes and alkynyl arenes from 1970 to 2019, covering mainly [4+2] cycloaddition reactions of vinyl- or acetylene-substituted furans, thiophenes, pyrroles, indoles, imidazoles, benzenes, and naphthalenes. The unique nature of the diene fragment in this type of intramolecular Diels-Alder reaction leads to the formation of heterocyclic structures with high selectivity. The review also highlights the detailed description of reaction mechanisms, particularly focusing on the thermal Diels-Alder reactions and subsequent aromatization process.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Mahboob Subhani, Jinrong Zhou, Yuguang Sui, Huijing Zou, Michael Frunzi, James Cross, Martin Saunders, Cijun Shuai, Wenjie Liang, Hai Xu
Summary: The study investigates the unique environment provided by studying isolated atoms or molecules within a fullerene cavity. The research focuses on the Diels-Alder addition reaction between 9,10-dimethyl anthracene and H-2@C-60, and characterizes the reaction using H-1 NMR spectroscopy.
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)