Article
Chemistry, Multidisciplinary
En Li, Jiean Chen, Yong Huang
Summary: The Michael reaction is an important method for preparing functional molecules with a β-stereogenic center. However, the enantioselective seleno-Michael addition is still poorly explored. In this study, a highly enantioselective Michael addition reaction of alkyl selenols to enones was reported, introducing a Se atom asymmetrically to an electron-deficient double bond. A chiral bifunctional N-heterocyclic carbene (NHC)/thiourea catalyst was developed and showed remarkable selectivity in delivering chiral β-seleno ketones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Milena Krstic, Maurizio Benaglia, Margherita Gazzotti, Eleonora Colombo, Miguel Sanz
Summary: Thiourea-based iminophosphorane (BIMP) organocatalysts, featuring SPhos- or BIDIME phosphine units, have been developed and applied successfully in the asymmetric addition reaction. alpha-Trifluoromethyl beta-nitroamines were obtained with high yields (40-82%) and enantioselectivities (80-95%) on N-Boc-protected trifluoromethyl aryl ketimines. The highest enantioselectivity (up to 95% ee) was achieved by using BIMPs derived from the combination of a chiral 1,2-amino alcohol-derived thiourea-organoazide and electron-rich phosphines via Staudinger reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Kenya Tamaribuchi, Jiaqi Tian, Kengo Akagawa, Kazuaki Kudo
Summary: Enantioselective Michael addition of beta-dicarbonyl compounds towards nitroalkenes was achieved using an immobilized, N-terminal-guanidinylated peptide catalyst. Various nucleophiles and electrophiles were employed, with the resin-supported catalyst being recyclable for five cycles. This method shows promise for industrial applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Ming-Hui Xu, Yong-Hai Yuan, Dong-Dong Liang, Xiao-Ming Zhang, Fu-Min Zhang, Yong-Qiang Tu, Ai-Jun Ma, Kun Zhang, Jin-Bao Peng
Summary: A novel spiro-pyrrolidine-derived bifunctional thiourea catalyst has been developed for stereoselective conjugate addition of furfurals to beta,gamma-unsaturated alpha-ketoesters. The rigid spirocyclic framework of the catalyst is essential for highly enantioselective transformation in the asymmetric trienamine catalysis of benzylic C-H functionalization of 5-benzylfurfurals.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Physical
Fangfang Guo, Jiean Chen, Yong Huang
Summary: Recently, chiral N-heterocyclic carbenes (NHCs) have been established as powerful catalysts for enantioselective bond-forming processes via noncovalent interactions. A bifunctional NHC with an embedded hydrogen-bonding motif has been reported in this study, showing remarkable tolerance of various Michael acceptors in an asymmetric aza-conjugate addition reaction, with catalytic efficiency far exceeding that of the benchmark tertiary amine-thiourea scaffold.
Article
Chemistry, Multidisciplinary
Hongkun Xu, Xuan Qin, Yaping Zhang, Chuan Wan, Rui Wang, Zhanfeng Hou, Xiaofeng Ding, Hailing Chen, Ziyuan Zhou, Yang Li, Chenshan Lian, Feng Yin, Zigang Li
Summary: The modification and functionalization of peptides play a crucial role in biotechnology and drug development. A highly reactive Michael-type warhead is reported here for the covalent modification of cysteine on peptides and proteins. By incorporating a vinyl group onto a methionine residue, the resulting vinyl sulfonium can be efficiently nucleophilically added by a suitable cysteine residue, leading to the formation of cyclized peptides. This peptide cyclization strategy demonstrates improved cell penetration and stability. Furthermore, a peptide ligand containing vinyl sulfonium can covalently bind to cysteine in the target protein, indicating the potential of vinyl sulfonium as a novel warhead for developing covalent peptide inhibitors.
CHINESE CHEMICAL LETTERS
(2022)
Article
Biochemistry & Molecular Biology
Xiao-Yan Dong, Da-Ming Du
Summary: This paper investigated the organocatalytic asymmetric 1,4-Michael addition reaction of azadienes and alpha-thiocyanoindanones, successfully synthesizing a series of chiral thiocyano compounds. By describing a possible reaction mechanism, it broadens the scope of application of azadiene substrates.
Article
Biochemistry & Molecular Biology
Yvette Lock Toy Ki, Armelle Garcia, Franck Pelissier, Tomasz K. Olszewski, Alicja Babst-Kostecka, Yves-Marie Legrand, Claude Grison
Summary: The Michael addition reaction was studied in the context of sustainability and efficiency through mechanochemistry. Eco-bases, derived from plants, were used as catalysts instead of classical bases, resulting in rapid and efficient reactions with low catalyst loading. The Eco-bases exhibited good recyclability and were effective in various Michael donors and acceptors. This study is significant for the development of mechanochemistry in sustainable chemistry.
Article
Chemistry, Organic
Jianli Zheng, Yingqian Xu, Shaorui Song, Ling Huang, Dongdong Cao, Aiguo Zhong, Jianguo Yang, Dingben Chen
Summary: The photoredox-catalyzed 1,6-difluoromethylation of 3-methyl-4-nitro-5-styrylisoxazole with HCF2SO2Na has been developed, yielding structurally diverse difluoromethylated products. The di-, tri-, and monofluoromethylation were compared, showing the highest yield for difluoromethylation. DFT calculations revealed the nucleophilicity of CF2H radical and the lowest transition state activation energy in the difluoromethylation reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Aabid A. Wani, Kriti Mehta, Rajeswara Reddy, Prasad V. Bharatam
Summary: This article reports the 1,1-diaminoazine-catalysed Michael addition reaction of malonates with nitro-olefins. The bifunctional nature of the catalyst facilitates the C-C bond formation.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Jiang-Song Zhai, Da-Ming Du
Summary: A bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reaction has been developed to synthesize chiral dispiro[indene-pyrrolidine-pyrimidine] compounds from 2-isothiocyanato-1-indanones and barbiturate-based olefins. The reaction has shown excellent yields and stereoselectivities. The synthetic utility of the products has been demonstrated through gram-scale synthesis, one-pot three-component reactions, and further transformation experiments.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Viktoria Kozma, Gyorgy Szollosi
Summary: In this study, asymmetric Michael additions of 1,3-dicarbonyl compounds to N-substituted maleimides were carried out using primary amine-(thio)phosphoramide bifunctional chiral organocatalysts derived from optically pure C-2-symmetric 1,2-diamines. The results show that the addition of ethyl 2-fluoroacetoacetate using the thiophosphoramide catalyst derived from 1,2-diphenylethane-1,2-diamine afforded succinimides substituted with fluorine bearing quaternary carbon in high yields, good diastereomeric ratios and excellent enantiomeric excesses. The bulkiness of the N-substituent of the maleimide ring influenced mostly the conversions. Additionally, the thiophosphoramide catalyst was found efficient in the addition of ethyl 2-fluoroacetoacetate to beta-nitrostyrenes.
MOLECULAR CATALYSIS
(2022)
Article
Chemistry, Organic
Steeva Sunny, Mohit Maingle, Kapileswar Seth
Summary: The application of bifunctional organocatalysts, specifically squaramides, in organic chemistry has significantly advanced due to their stability, low toxicity, ease of handling, and recoverability. This review article provides a comprehensive report on the fine-tunable bifunctional chiral squaramide-catalyzed sulfa-Michael addition, emphasizing the construction of complex molecular entities with multiple stereocenters. The article also summarizes the progress made in chiral squaramide-catalyzed asymmetric sulfa-Michael addition and subsequent cascade reactions between 2011 and 2022.
Article
Polymer Science
Susanne M. Fischer, Viktor Schallert, Johanna M. Uher, Christian Slugovc
Summary: In this study, we propose a method for preparing crosslinked polymers from off-stoichiometric oxa-Michael formulations, by a self-limiting base catalyzed reaction between difunctional Michael acceptors and substoichiometric amounts of diols, followed by anionic polymerization of the remaining vinyl groups. The properties of the resulting polymers can be easily tuned by varying the amount of diols.
Article
Chemistry, Physical
Diana Salazar Illera, Roberta Pacifico, Mauro F. A. Adamo
Summary: Herein, we report a method for the addition of acidic gamma-butenolide and N-Boc-pyrrolidone to 4-nitro-5-styrylisoxazoles, a popular class of cinnamic ester synthetic equivalent. The reactions were catalyzed by Cinchona-based phase-transfer catalysts, resulting in good isolated yields and moderate enantioselectivity (up to 74% ee) of functionalized gamma-butenolides.
Article
Chemistry, Multidisciplinary
Bin Wu, Naohiko Yoshikai
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Organic
Bin Wu, Rena Chopra, Naohiko Yoshikai
Review
Chemistry, Organic
Bin Wu, Naohiko Yoshikai
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Inorganic & Nuclear
Naohiko Yoshikai, Mithun Santra, Bin Wu
Article
Chemistry, Multidisciplinary
Bin Wu, Melvina, Xiangyang Wu, Edwin Kok Lee Yeow, Naohiko Yoshikai
Article
Chemistry, Multidisciplinary
Bin Wu, Naohiko Yoshikai
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2013)
Article
Chemistry, Multidisciplinary
Bin Wu, Mithun Santra, Naohiko Yoshikai
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2014)
Article
Chemistry, Multidisciplinary
Zhi-Cong Geng, Ning Li, Jian Chen, Xiao-Fei Huang, Bin Wu, Guo-Gui Liu, Xing-Wang Wang
CHEMICAL COMMUNICATIONS
(2012)
Article
Chemistry, Organic
Bin Wu, Jian Chen, Mei-Qiu Li, Jin-Xin Zhang, Xiao-Ping Xu, Shun-Jun Ji, Xing-Wang Wang
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2012)
Article
Chemistry, Applied
Daniel J. Lippincott, Evan Landstrom, Margery Cortes-Clerget, Bruce H. Lipshutz, Klaus Buescher, Robert Schreiber, Corinne Durano, Michael Parmentier, Ning Ye, Bin Wu, Min Shi, Hongwei Yang, Martin Andersson, Fabrice Gallou
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2020)
Article
Chemistry, Applied
Min Shi, Ning Ye, Wei Chen, Hui Wang, Chiming Cheung, Michael Parmentier, Fabrice Gallou, Bin Wu
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2020)
Article
Chemistry, Multidisciplinary
Ning Ye, Bin Wu, Kangming Zhao, Xiaobin Ge, Yu Zheng, Xiaodong Shen, Lei Shi, Margery Cortes-Clerget, Morgan Louis Regnier, Michael Parmentier, Fabrice Gallou
Summary: A robust and sustainable C(sp(2))-C(sp(3)) cross-electrophile coupling was successfully achieved under micellar conditions using nickel/copper synergistic catalysis, providing a general method to access alkylated arenes with good to excellent yields on a very large scale.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Applied
Bin Wu, Sisi Zhang, Tao Hong, Yizong Zhou, Hui Wang, Min Shi, Hongwei Yang, Xiangguang Tian, Jing Guo, Jianwei Bian, James Roache, Pete Delgado, Ruowei Mo, Cary Fridrich, Feng Gao, Jianhua Wang
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2020)
Article
Chemistry, Multidisciplinary
Bin Wu, Junliang Wu, Naohiko Yoshikai
CHEMISTRY-AN ASIAN JOURNAL
(2017)
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)