Article
Chemistry, Organic
Dilip V. Patil, Karu Ramesh, Hun Young Kim, Kyungsoo Oh
Summary: The visible light excitation of areneazo-2-(2-nitro)-propane center dot HCl salts generated singlet aryl cation that underwent aromatic S(N)1 reactions with various nucleophiles. The stabilization of the in situ generated singlet aryl cation by a counter nitronate anion prevented other intersystem crossing and single electron transfer processes. With improved safety features, the current visible light-promoted reactions provide an alternative strategy for aryl C-sp(2)-X bond formation.
Review
Chemistry, Organic
Xin Zhang, Yaoyao Mei, Yangyang Li, Jingang Hu, Dayun Huang, Yicheng Bi
Summary: This review discusses the advances of aryl diazonium salts in light-mediated reactions, categorizing them into five groups based on the types of bond formations. Various reactions such as radical addition, metal-catalyzed coupling, and C-H activation are discussed in this context.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Ying Fu, Liang-Liang Guo, Xi Chen, Hao Chen, Jia-Jia Liu, Fang-Rong Li, Cai-Qin Xiao, Zhengyin Du
Summary: A Cu/Pd co-catalyzed Catellani-type ortho arylation reaction of iodoarenes with aryl diazonium salts has been developed. Aryl radicals that derived from aryl diazonium salts were regioselectively installed at ortho position of iodoarenes via palladium catalyzed C-H activation. Mechanistic studies showed that, in contrast to classical Pd0-PdII-PdIV-PdII-Pd0 catalytic cycle, this radical cascades performed via a Pd0-PdII-PdIII-PdI-Pd0 cycle.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Organic
Jitender Singh, Anoop Sharma, Anuj Sharma
Summary: Allenes are attractive molecules for the synthesis of bioactive compounds and naturally occurring products. In recent years, visible light mediated photoredox catalysis has emerged as a powerful method for the functionalization of allenes, contributing significantly to the field.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Qiuli Yan, Wenwen Cui, Xiuyan Song, Guiyun Xu, Min Jiang, Kai Sun, Jian Lv, Daoshan Yang
Summary: An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported, using a single ligand Cu-I photocatalyst formed in situ for the transformation. Diverse organosulfones were obtained in moderate to good yields, demonstrating a promising approach toward the synthesis of diverse and useful organosulfones.
Article
Chemistry, Multidisciplinary
Bin Wang, Long Zou, Lei Wang, Manman Sun, Pinhua Li
Summary: A simple and efficient visible-light-induced photoredox-catalyzed diarylation of N-methacryloyl-2-arylbenzoimidazoles with aryl diazonium salts was developed in this study. The reaction provides a convenient access to a variety of benzimidazoisoquinolinones through the construction of two C-C bonds in one step under mild reaction conditions. The research was published by Elsevier B.V. and all rights are reserved.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Physical
Youcan Zhang, Zhi-Peng Bao, Chang-Sheng Kuai, Xiao-Feng Wu
Summary: Here, we have developed a direct and effective synthesis strategy for sulfur-containing carboxylic acid derivatives through copper/visible light catalyzed ring-opening carbonylation of sulfonium salts. The protocol utilizes photoredox to selectively cleave the C(sp3)-S bond of sulfonium salts, while sequentially functionalizing to form vicinal C-C and C-X (X = O or N) bonds in the presence of carbon monoxide and nucleophiles. Various substrates were successfully transformed into desired carbonylated products with moderate to good yields, displaying good functional group tolerance and excellent chemoselectivity. Importantly, this approach can be easily extended to late-stage modification of bioactive molecules.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Organic
Pieterjan Winant, Wim Dehaen
Summary: A metal-free protocol for the direct bis-arylation of 2,5-dichlorobenzoquinone with aryldiazonium salts is reported in this study. The reactive salts are generated in situ and converted to radicals through irradiation with visible light. Furthermore, reaction products precipitate from the solvent, eliminating the need for purification and providing a novel green method for the synthesis of versatile bis-electrophiles.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Silvia Gaspa, Luca Ledda, David d'Atri, Andrea Porcheddu, Luisa Pisano, Massimo Carraro, Lidia De Luca
Summary: An esterification of the C-H bond of aldehydes is achieved using oxidovanadium(IV) sulfate as a catalyst. The reaction is facilitated by visible-light irradiation, performed at room temperature, and requires no additives, with H2O2 as the benign oxidant. This study showcases the potential of vanadium salts in halogenation processes, C-H activation, and contributes to the field of earth-abundant metal-based catalysis.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Qiyue Wang, Xinyu Hao, Kun Jin, Rong Zhang, Chunying Duan, Yaming Li
Summary: A novel photo-induced C-H arylation of (hetero)arenes using aryl selenonium salts as an aryl source has been developed. The method involves C-Se bond activation under blue LED irradiation, enabling the arylation of aromatic (hetero)cyclic compounds. The method utilizes safe and clean energy and yields site-selective biphenyl or bi-heterocyclic products in medium to good yields. In addition, the borylation and Sonogashira coupling of aryl selenonium salts also proceed in good yields. Results demonstrate that selenonium salts are more reactive than sulfonium salts.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ramanand Das, Taraknath Kundu, Joneswar Basumatary
Summary: An efficient photoredox protocol for the diazenylation of 1,3-diones is presented. C-N bond formation through Csp3-H functionalization of cyclic and alkyl diones by unstable aryl diazenyl radicals is achieved using aryldiazonium tetrafluoroborates and organocatalysts under visible light irradiation. The reaction has broad substrate scope, high yields, and can be performed efficiently in water as a green solvent. This method provides easy access to aryldiazenyl derivatives, which are valuable starting materials for the synthesis of aza heterocycles and potential pharmacophores.
Article
Chemistry, Organic
Min Zheng, Ke Gao, Yanhu Zhang, Hongjian Lu
Summary: An aryl radical in situ SO2-capture reaction was reported for the first time, using aryl diazonium salts as aryl radical precursors and vinyl triflates and allyl(alkynyl) trifluoromethylsulfones as radical acceptors and in situ SO2 donors. The reaction can produce various beta-keto, allyl, and alkynyl arylsulfone derivatives under mild visible-light photoredox-catalytic conditions without requiring external SO2 sources.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Guo-Qin Hu, Wen-Yan Zhang, Yong-Xin Liu, Jing-Hui Liu, Bin Zhao
Summary: Here, we present a decarboxylative thiocarbonylation method of aryl and alkenyl sulfonium salts using oxalic acid monothioethers (OAMs) under visible light-accelerated palladium catalysis. The reaction demonstrates a new application of visible light-accelerated palladium catalysis in catalytic decarboxylative cross-couplings, allowing the synthesis of different types of thioester compounds. Both sulfonium salts and OAMs are easily accessible and stored reagents.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Da-Liang Zhu, Jie Li, David James Young, Yanqing Wang, Hong-Xi Li
Summary: This paper presents a mild strategy for aminating aryl halides with anilines using dual photoredox and nickel catalysis. Thioxanthen-9-one, an inexpensive and readily available compound, greatly enhanced this cross-coupling reaction, yielding a diverse range of diarylamines in good yields (41-93%) at room temperature. The reaction could be performed under compact fluorescent lamp light or sunlight and was tolerant of various functional groups. It was successfully applied to the synthesis of natural products and drug molecules, even at a gram-scale. The mechanism involves several steps including oxidative addition, transmetalation, energy transfer, and reductive elimination.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Ming-Hang Bi, Ying Cheng, Wen-Jing Xiao, Jia-Rong Chen
Summary: This study describes a selective three-component 1,4-difluoroalkylesterification enabled by dual photoredox and copper catalysis. The protocol utilizes commercially available CF2-reagents as radical precursors and carboxylic acids as oxygen-based nucleophiles, allowing access to difluoroalkylated allylic esters. Furthermore, this protocol can also be extended to intramolecular two-component 1,4-difluoroalkylesterification for the synthesis of 3-substituted benzobutyrolactones. Preliminary mechanistic studies provide evidence for a radical process.
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)