Article
Chemistry, Organic
Venkatachalam Pitchumani, Martin Breugst, David W. Lupton
Summary: This study demonstrates the enantioselective conversion of beta-substituted acrylamides to enantioenriched quinolones using electron-withdrawing protection and moderate nucleophilicity N-heterocyclic carbenes. The reaction shows complete diastereoselectivity, good yield, and modest enantioselectivity. Computational studies support the concept of decreased amide bond character with electron-withdrawing protection of the nitrogen.
Article
Multidisciplinary Sciences
Aleksandra Buchcic-Szychowska, Stanislaw Lesniak, Michal Rachwalski
Summary: A series of chiral aziridines with a phosphine moiety were synthesized and used as organocatalysts in the asymmetric intramolecular Rauhut-Currier reactions of p-quinone derivatives. The desired chiral phenols were obtained with high yields and satisfactory enantiomeric excess values.
Article
Chemistry, Multidisciplinary
Juan Zhang, Wei Hao, Ying Chen, Zhen Wang, Jinzhong Yao, Weijun Yao
Summary: We have disclosed a method for the construction of exo-bicyclic succinimide derivatives through the Rauhut-Currier reaction and Diels-Alder reaction, exhibiting high stereospecificity and close to quantitative yields.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Sei-Hyun Choi, Byungsun Jeon, Namho Kim, Hsin-Hui Wu, Tzu-Ping Ko, Mark W. Ruszczycky, Eta A. Isiorho, Yung-Nan Liu, Adrian T. Keatinge-Clay, Ming-Daw Tsai, Hung-Wen Liu
Summary: The catalog of enzymes catalyzing nucleophile-assisted formation of C-C bonds is limited, with no definitive example of a biological RauhutCurrier reaction known. SpnL, in conjunction with SpnF, is implicated in catalyzing a potential biological Rauhut-Currier reaction, but further research is needed to fully understand the mechanism.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Multidisciplinary
Subhankar Biswas, Nimisha Bania, Subhas Chandra Pan
Summary: Intermolecular cross Rauhut-Currier reactions have gained significant attention in recent years due to their ability to produce complex structures with good regio- and stereo- selectivity using various catalysts. This review highlights the recent developments in these reactions, involving both achiral and chiral catalysts, resulting in products with diverse utilities. Furthermore, detailed mechanistic studies of these reactions are also presented.
Article
Chemistry, Organic
Juan Ye, Yang Wang
Summary: A comprehensive study on the mechanisms and origins of the chemoselectivity and regioselectivity of phosphine-catalyzed Rauhut-Currier reaction is performed by DFT. The computational results reveal that the cross R-C reaction is energetically favorable, with head-to-tail product being generated preferentially. The C-C bond formation process is identified as the determining step for regioselectivity and chemoselectivity.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Nimisha Bania, Buddhadeb Mondal, Sounak Ghosh, Subhas Chandra Pan
Summary: In this study, unsaturated pyrazolones were used in the Rauhut-Currier reaction for the first time, leading to the successful synthesis of trisubstituted tetrahydropyrano[2,3-c]pyrazoles with excellent diastereoselectivities. The synthesis of disubstituted tetrahydropyrano[2,3-c]pyrazoles was also demonstrated, and a catalytic asymmetric version of the process was preliminarily studied using chiral DMAP catalysts.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Chun-Ting Chou, Chun-Wei Lu, Bing-Syuan Wu, Cheng-Che Tsai
Summary: This paper describes the study on the kinetic resolution of racemic secondary alcohols (O-nucleophiles) via stereoselective intramolecular allylic substitution. The reaction was achieved by the synergistic catalysis of palladium and chiral phosphoric acid, yielding chiral cis-1,3-disubstituted 1,3-dihydroisobenzofurans with a selective factor of up to 60.9 and a diastereomeric ratio of up to 7.8:1. The application of this methodology in the asymmetric synthesis of a compound with antihistaminic activity was demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Wu-Wei Dong, Kui Tian, Xiu-Qin Dong, Chun-Jiang Wang
Summary: A series of structurally novel multifunctional chiral aminophosphine catalysts were developed through a concise synthetic strategy. These catalysts were successful in catalyzing the highly enantioselective intermolecular cross Rauhut-Currier reactions between vinyl ketones and 3-acyl acrylates and 2-ene-1,4-diones, generating a wide range of structurally important chiral multicarbonyl products with high stereocontrol.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Bendu Pan, Jia-Sheng Ouyang, Yaqi Zhang, Hao Liang, Qiang Ni, Bin Chen, Xiaoyun Pu, Long Jiang, Rihui Cao, Liqin Qiu
Summary: The iridium-catalyzed intramolecular asymmetric allylic etherification of salicylic acid derivatives was successfully achieved for the first time, producing novel chiral 1,4-benzoxazepinones with good yields and high enantioselectivities. Compared to other ligands, L7 showed obvious advantages in catalytic activity and enantioselectivity. The method demonstrated mild conditions and a wide substrate scope, making it practical for application.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Fang Xie, Jie Zhao, Deyue Ren, Jianming Xue, Jingyi Wang, Qin Zhao, Lu Liu, Xiaodan Liu
Summary: A Cu-catalyzed coupling reaction between cyclic imino esters and 2H-azirines has been developed, allowing for the synthesis of novel optically active aziridines in high yields and with excellent levels of diastereo- and enantioselectivities under mild conditions. This method features a broad substrate scope, good functional group compatibility, and enriches the existing reaction type for the rapid synthesis of optically active aziridines bearing vicinal tetrasubstituted stereogenic carbon centers.
Article
Chemistry, Organic
Rajkiran Kumari, Ajit Kumar Jha, Sophiya Goyal, Reena Maan, S. Rajagopala Reddy, Srinivasan Easwar
Summary: A serendipitous Rauhut-Currier dimerization of 1,1-disubstituted activated olefins was observed in the presence of DABCO. The reaction produces multifunctionalized enol esters with yields greater than 90% in most cases, without the need for column chromatographic purification. The acyl transfer is believed to occur via a Morita-Baylis-Hillman (MBH) reaction transition state, supported by computational calculations.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Satish B. Thopate, Lakshmi Revati Magham, Shrabani Dinda, Rambabu Chegondi
Summary: This work presents the development of an unconventional and highly enantioselective solvent-promoted Rauhut-Currier cyclization of enal-tethered cyclohexadienone. The reaction involves the reactivity of a Jorgensen-Hayashi catalyst through the merging of iminium and enamine activation. The asymmetric desymmetrization reaction shows broad substrate scope with good yields and high to excellent enantioselectivity. DFT calculations suggest that the rate-limiting step is the elimination of the alkoxy group, which proceeds through proton abstraction by solvent instead of a direct 1,3-proton shift.
Article
Chemistry, Multidisciplinary
Dragana Stevanovic, Jovana Bugarinovic, Marko Pesic, Anka Todosijevic, Goran A. Bogdanovic, Ivan Damljanovic
Summary: A simple protocol has been developed for the synthesis of multifunctional ferrocene derivatives. The study showed that the strong electron-donating group at the beta-position of nitroalkenes prevents polymerization and stabilizes the intermediate.
Review
Chemistry, Organic
Li Xin, Song Qiuling
Summary: Chiral boranes have emerged as privileged catalysts in asymmetric reactions due to their lower catalyst loading and easier access compared to chiral transition metal catalysts. This article summarizes and discusses the chiral borane-catalyzed enantioselective reactions, organized into three parts based on reaction categories.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
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)