Article
Chemistry, Multidisciplinary
Pallab Karjee, Santu Mandal, Bijoy Debnath, Nirali Namdev, Tharmalingam Punniyamurthy
Summary: Efficient annulation of in situ formed azaoxyallyl cations using diaziridines has been achieved at room temperature with the aid of a base, leading to the formation of 1,2,4-triazines. The practical advantages of this reaction include its broad substrate scope, scalability, high tolerance towards functional groups, and the absence of transition-metal catalysts.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Yue Ren, Wangyu Shi, Yi Tang, Shixiang Piao, Songcheng Yu, Yongjun Wu, Hongchao Guo
Summary: A series of gamma-substituted MBH carbonates were synthesized and reacted with electrophilic exocyclic alkenes through phosphine-catalyzed annulations, resulting in the formation of valuable spirocyclopentenes with moderate to excellent yields and diastereoselectivities. The annulation process tolerates a wide range of MBH carbonates with gamma-hydrogen, alkenyl, and alkynyl substituents. Notably, this annulation involves the beta, gamma, and delta carbons of MBH carbonates, which is unprecedented.
Article
Chemistry, Organic
Wen-Kang Wang, Fei-Yun Bao, Si-Tian Wang, Sheng-Yin Zhao
Summary: A method for preparing 3-aminomethylated maleimides via Morita-Baylis-Hillman (MBH) reaction was developed. This study used maleimides and 1,3,5-triazinanes as substrates, and through the phosphine-catalyzed coupling, a series of 3-aminomethylated maleimide derivatives were obtained with a yield of 41-90%. Acylation, isomerization, and Michael addition reactions demonstrated the synthetic application of this method. Control experiments revealed that phosphorus ylide formation and elimination occur during the reaction pathway.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Zhongtao Yang, Xiai Luo, Zhipeng Zhang, Xiaoling Luo, Jia Zheng, Hui Luo, Weiguang Yang
Summary: In this study, a silver-catalyzed [3+2] diastereoselective annulation of p-quinamines and ketenimine zwitterionic salts was successfully carried out, leading to the synthesis of new compounds with specific stereochemical configurations. The relative stereoselectivity of the reaction can be controlled by specific functional groups. This method is significant for expanding the application of ketenimine zwitterionic salts.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Michael P. Doyle, Ming Bao
Summary: This study achieved a highly enantioselective synthesis of substituted pyrrolidines and 1,2-oxazinanes via stereoretentive [3 + 2]/[3 + 3]-cycloaddition of nonracemic donor-acceptor cyclopropanes with imines, triazines, and nitrones. The reactions were conducted under mild conditions and showed good to high yields with broad applicability. Compared to previous approaches using racemic cyclopropane reactants and chiral ligand catalysts, this study utilized enantioenriched donor-acceptor cyclopropanes as reactants with achiral catalysts.
Article
Chemistry, Organic
Kana Sakamoto, Takahiro Nishimura
Summary: This study describes a highly enantioselective intramolecular hydroarylation reaction using C-H activation, catalyzed by an iridium catalyst and a chiral bisphosphine ligand. The carbonyl group of ketones serves as an effective directing group, allowing for efficient synthesis of chiral 3-substituted dihydrobenzofurans in high yields and enantioselectivity from readily available starting materials. The reaction showcases the potential for developing a more efficient and selective variant of the reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Ke Li, Zhenjie Gan, Er-Qing Li, Zheng Duan
Summary: A novel phosphine-catalyzed (4 + 2) cyclization reaction has been reported for the generation of functionalized dihydropyran skeletons from electron-deficient conjugated dienes and enones. Mechanistic investigation reveals the formation of a new phosphonium zwitterion, which undergoes consecutive reactions. An asymmetric variant has also been developed through efficient and economical chiral phosphine catalysis.
Article
Chemistry, Organic
Gang Yang, Lin Yao, Guojiang Mao, Guo-Jun Deng, Fuhong Xiao
Summary: We have reported a metal-free protocol for the synthesis of indenoquinolinones and 2-substituted quinolines via [4 + 2] cycloaddition reaction using readily available 2-aminobenzaldehydes and ketones as starting materials. Different quinoline derivatives can be selectively synthesized by changing the type of ketones. O-2 and dimethyl sulfoxide (DMSO) as co-oxidants play an important role in the synthesis of indenoquinolinones. This condensation/oxidation strategy involves the formation of C-N, C-C, and C-O bonds, with the advantages of high yields and a broad substrate range.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Gang Yang, Lin Yao, Guojiang Mao, Guo-Jun Deng, Fuhong Xiao
Summary: A metal-free protocol for the synthesis of indenoquinolinones and 2-substituted quinolines using readily available 2-aminobenzaldehydes and ketones has been reported. Different quinoline derivatives can be selectively synthesized by altering the type of ketones.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Guangming Wei, Dongling Zheng, Chen Li, Zhengkai Chen, Xiao-Feng Wu
Summary: Trifluoromethyl-substituted 1,2-dihydroquinoxalines and diimines can be synthesized efficiently through a base-mediated cascade reaction involving the unusual N-N bond cleavage and rearrangement of azo compounds.
Article
Chemistry, Organic
Wen-Bi Hu, Yan-Qing Qiu, Wen-Yi Wei, Qing Li, Yan-Jun Xu
Summary: In this study, novel complex C2-quaternary-indol-3-one units bearing versatile nitro groups were successfully developed from pseudo-indolones and alpha,beta-unsaturated nitroolefins through rhodium-catalyzed C-H activation/[3 + 2] spirocyclization. Notably, four diastereomers could be selectively obtained in the reaction by condition control.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hui Chen, Mo Yang, Guoqiang Wang, Liuzhou Gao, Zhigang Ni, Jingxiang Zou, Shuhua Li
Summary: A borane-catalyzed sequential addition of terminal alkynes to para-substituted phenols has been developed, yielding ortho-propargylic alkylated phenols with congested quaternary carbons. Control experiments and DFT calculations suggest a sequential phenol alkenylation/hydroalkynylation process. The extension of this strategy to the construction of triaryl-substituted quaternary carbons demonstrates the broad utility of this method.
Article
Chemistry, Organic
Chengjun Wu, Xiaoqin Bian, Lizhong Wang, Yue Zhang, Cunde Wang
Summary: An efficient protocol for the synthesis of valuable pyrimidine-4,6-diamines from readily available compounds has been developed. This method provides moderate to high yields under simple reaction conditions and allows for modifications of complex bioactive molecules, showing potential applications in medicinal chemistry.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Jin Xi, Ding Wang, Jinxia Hu, Huan Shen, Tao Wang, Zunting Zhang
Summary: A method for synthesizing benzo[f]quinoline derivatives via photoinduced 6 pi-electrocyclization has been developed. The reaction conditions are mild, and the yields are high without the need for transition metal catalysts or additives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhimin Ying, Jie Cen, Feng Luo, You Wu, Shuangrong Liu, Wenteng Chen, Jiaan Shao, Yongping Yu
Summary: A novel domino annulation/oxidation reaction using heterocyclic ketene aminals and 2-aminochalcones has been developed for the selective synthesis of poly-substituted benzo[f]imidazo[2,1-a][2,7]naphthyridines and 3-azaheterocyclic substituted 2-arylquinolines. The reactions proceed smoothly under mild conditions without any additives. The synthesized benzo[f]imidazo[2,1-a][2,7]naphthyridine 3g exhibited a fluorescence effect, indicating potential applications in organic optical materials.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Nanoscience & Nanotechnology
A. R. Kytsya, L. I. Bazylyak, I. Yu. Zavaliy, Yu. V. Verbovytskyy, P. Zavalij
Summary: Bimetallic Ni-Cu nanoparticles with different (Ni/Cu) ratio were synthesized through a fast and simple reduction process in water/ethylene glycol solutions. The nanoparticles showed polydisperse sizes within 20-70 nm, with the particle diameter slightly depending on the Ni/Cu ratio. Additionally, XRD and EDX analyses revealed changes in lattice parameters and core-shell structure, respectively.
APPLIED NANOSCIENCE
(2022)
Article
Chemistry, Physical
Kuiyong Dong, Haifeng Zheng, Yongliang Su, Ahmad Humeidi, Hadi Arman, Xinfang Xu, Michael P. Doyle
Summary: Catalyst-directed access leads to the formation of three different products from the same reactants involving different metals, showcasing the tremendous potential of this approach for diversity-oriented synthesis.
Article
Chemistry, Multidisciplinary
Yong-Liang Su, Kuiyong Dong, Haifeng Zheng, Michael P. Doyle
Summary: A new catalytic methodology for synthesizing pyrazolines from alpha-diazo compounds and conjugated alkenes was reported. The regiocontrolled addition of diazomethyl radicals to carbon-carbon double bonds followed by intramolecular ring closure and tautomerization achieved a diverse set of pyrazolines in good yields with excellent regioselectivity. This strategy overcomes the limitations of electron-deficient alkenes and opens new opportunities for versatile transformations of diazo compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Haifeng Zheng, Isa Faghihi, Michael P. Doyle
Summary: The study demonstrated that beta-Aryl/alkyl vinyl diazoacetates can participate in metallo-vinylcarbene reactions with nitrones, leading to a Rh-2(OAc)(4)-catalyzed cyclopropene dimerization reaction and a copper(I) catalyzed [3+3]-cycloaddition of nitrones. By employing chiral cyclopropyl-In-SaBox ligand with copper(I) catalysis, the asymmetric version of the cycloaddition reaction was achieved, delivering various 3,6-dihydro-1,2-oxazine derivatives in good yield and with excellent enantioselectivity under mild conditions.
HELVETICA CHIMICA ACTA
(2021)
Review
Chemistry, Organic
Yong-Liang Su, Michael P. Doyle
Summary: α-Aminoalkyl radicals are easily synthesized and used as reaction activators to transform organic halides or sulfonium salts into highly reactive radical species. This review summarizes the emerging chemistry in the field, providing new pathways for transformations of halides and sulfonium salts.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Physical
Yong-Liang Su, Geng-Xin Liu, Luca De Angelis, Ru He, Ammar Al-Sayyed, Kirk S. Schanze, Wen-Hao Hu, Huang Qiu, Michael P. Doyle
Summary: This study demonstrates the efficient generation of functionalized derivatives through photocatalyzed multicomponent reactions using nitrogen aromatic heterocycles, alkenes, and diazo compounds. The reaction shows high functional group tolerance and exacting regioselectivities. Mechanistic studies, including photophysical measurements, provide insights into this radical cascade reaction.
Article
Chemistry, Organic
Gildardo Rivera, Luca De Angelis, Ammar Al-Sayyed, Soumen Biswas, Hadi Arman, Michael P. Doyle
Summary: A convenient, efficient, and inexpensive method has been developed for the synthesis of 1,2,3-triazine derivatives via deoxygenation of 1,2,3-triazine 1-oxide using trialkyl phosphites. This method provides a range of aromatic and aliphatic substituted 1,2,3-triazine-4-carboxylate derivatives cleanly in high yields. Unexpected 1,2,4-triazine derivatives were also obtained as minor products.
Article
Chemistry, Multidisciplinary
Ming Bao, Xiongda Xie, Jingjing Huang, Michael P. Doyle, Zhi Ren, Haibo Yue, Xinfang Xu
Summary: In this study, an Ag/Au-catalyzed cascade reaction of alkyne embedded diazoketones with indoles has been reported. Mechanistic studies indicate that the reaction involves a [4+2] cycloaddition followed by a retro-Michael addition/carbene N-H insertion process with gold catalysis, and a dearomatization/rearomatization sequence with silver catalysis, leading to the selective construction of N-doped polycyclic aromatic hydrocarbons (PAHs) with diverse structures and functional groups.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Ming Bao, Karlos Lopez, Raj Gurung, Hadi Arman, Michael P. Doyle
Summary: A highly enantioselective synthesis of chiral dihydro-3H-carbazole-2-carboxylate derivatives is achieved via a one-pot cascade reaction catalyzed by nickel(II) perchlorate hexahydrate and scandium(III) trifluoromethanesulfonate. The reaction proceeds under mild conditions and provides the desired products in high yields and enantioretention. Furthermore, these dihydro-3H-carbazole-2-carboxylates can be transformed into decarboxylated compounds through hydrolysis and decarboxylation under unexpectedly mild reaction conditions, giving moderate yields with high retention of enantiomeric purity.
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, Organic
Soumen Biswas, Luca De Angelis, Gildardo Rivera, Hadi Arman, Michael P. Doyle
Summary: 1,2,3-Triazine 1-oxides are highly effective substrates for inverse electron demand Diels-Alder reactions. These stable heterocyclic compounds, formed from vinyldiazoacetates via reaction with tert-butyl nitrite, undergo clean nucleophilic addition reactions with amidines to form pyrimidines, with beta-ketocarbonyl compounds and related nitrile derivatives to form polysubstituted pyridines, and with 3/5-aminopyrazoles to form pyrazolo[1,5-a]pyrimidines, in high yields. These reactions, catalyzed by bases, are rapid at room temperature and allow for a range of structural modifications.
Article
Chemistry, Organic
Michael P. Doyle, Ming Bao
Summary: This study achieved a highly enantioselective synthesis of substituted pyrrolidines and 1,2-oxazinanes via stereoretentive [3 + 2]/[3 + 3]-cycloaddition of nonracemic donor-acceptor cyclopropanes with imines, triazines, and nitrones. The reactions were conducted under mild conditions and showed good to high yields with broad applicability. Compared to previous approaches using racemic cyclopropane reactants and chiral ligand catalysts, this study utilized enantioenriched donor-acceptor cyclopropanes as reactants with achiral catalysts.
Article
Multidisciplinary Sciences
Luca De Angelis, Chao Pei, Ana L. Narro, Daniel Wherritt, Rene M. Koenigs, Michael P. Doyle
Summary: The synthesis and characterization of organic compounds with unique atom or functional group connectivity is a significant interest for chemists. Polycarbonyl compounds, in which multiple carbonyl groups are directly adjacent and influence each other's reactivity, have been extensively studied. However, little is known about 1,2,3,4-tetracarbonyl compounds. In this study, a synthesis strategy involving C-nitrosation of enoldiazoacetates is reported, which allows for the synthesis of 1,2,3,4-tetracarbonyl compounds where each carbonyl group is orthogonally masked.
NATURE COMMUNICATIONS
(2023)
Review
Chemistry, Physical
Ming Bao, Michael P. Doyle
Summary: The [3+n]-cycloaddition reactions using chiral catalysts and racemic cyclopropanes or achiral catalysts and chiral, non-racemic cyclopropanes have proven to be important transformations for the synthesis of carbocyclic and heterocyclic compounds, showing both mechanistic and structural advantages in ring formation.
Article
Chemistry, Physical
Ming Bao, Karlos Lopez, Raj Gurung, Hadi Arman, Michael P. Doyle
Summary: A highly enantioselective synthesis of chiral dihydro-3H-carbazole-2-carboxylate derivatives is achieved via a one-pot cyclopentannulation-rearrangement cascade reaction. The reaction is catalyzed by nickel(II) perchlorate hexahydrate and scandium(III) trifluoromethanesulfonate, and involves the use of 3-methylindole and non-racemic donor-acceptor cyclopropanes. The resulting products show high yields and enantioretention under mild reaction conditions, and further transformation into decarboxylated compounds can be achieved with moderate yields and high enantiomeric purity.
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)
