Article
Chemistry, Organic
Cheng Huang, Zhifei Zhao, Shiwu Li, Jixing Zhao, Leifang Wu, Chengzhi Gu
Summary: A highly enantioselective conjugate addition has been developed for the reaction between indolizine and its analogues with alpha,beta-unsaturated 2-acyl imidazoles. This method provides excellent yields and enantioselectivities, overcoming the limitations of organocatalysts in controlling stereoselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Yunlong Zhao, Rou Xiao, Weibin Fang, Junling Zhao
Summary: This study presents a protocol for the highly selective addition reaction of isatin-derived beta,gamma-unsaturated alpha-ketoesters with 4-aminoindoles at the C7 position. The reaction, catalyzed by a SPINOL-derived chiral phosphoric acid, yields bisindole derivatives with up to 97% enantiomeric excess. Further biological testing revealed that the products have high cytotoxicity against various cancer cell lines.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Xi Xiao, Xiaobiao Lu, Ming Zhang, Haoqing Hou, Changfeng Wan, Jinbiao Liu
Summary: A novel synthetic method was successfully developed for the preparation of multisubstituted dihydrochromeno[2,3-b]indole derivatives in moderate to high yields using a catalytic environmentally benign iron salt.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Takanori Shibata, Mio Sasaki, Masafumi Kojima, Mamoru Ito
Summary: The chiral Ir(I)-catalyzed intermolecular reaction of N-carbamoylpyrrole and indole derivatives with alpha,beta-unsaturated carbonyl compounds proceeded with high enantioselectivity, yielding chirally functionalized pyrroles and indoles as formal C-H conjugate adducts. The reaction mechanism was further investigated through deuterium labeling experiments.
Article
Chemistry, Organic
Yifei Qu, Xiaojia Cai, Yuzhuang Guan, Jiamin Tan, Zhangping Cai, Minyun Liu, Yasi Huang, Jinhui Hu, Wen-Hua Chen, Jia-Qiang Wu
Summary: A facile and straightforward method for the successful synthesis of difluoromethylated indole-3-carbinols, bisindolylmethanes, and indole-3-methanamines by a Friedel-Crafts reaction is developed, showing good to excellent yields, broad substrate compatibility, good functional group tolerance, and scalability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Yuanai Fei, Jun Hou, Huiying Song, Mei-li Yang, Pan Lei, Xiayu Ge, Hongbo Wei, Yuanzhen Xu, Weiqing Xie
Summary: An asymmetric Friedel-Crafts alkylation reaction has been developed for the construction of 3-substituted 3'-indolyloxindoles using in situ generated indol-2-one from functionalized 3-bromooxinidole catalyzed by chiral N,N'-dioxide/Ni(BF4)(2). High yields and enantioselectivities (up to 99% ee) were achieved for the synthesis of these compounds. Furthermore, the potential use of the resulting 3-substituted 3'-indolyloxindole as a key intermediate for the formal synthesis of (+)-folicanthine was demonstrated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Bingfei Peng, Jiguo Ma, Jianhua Guo, Yating Gong, Ronghao Wang, Yi Zhang, Jinlong Zeng, Wen-Wen Chen, Kuiling Ding, Baoguo Zhao
Summary: By developing a new type of strong Bronsted C-H acids, the activity and enantioselectivity of catalytic reactions can be significantly improved, expanding the field of asymmetric Bronsted acid catalysis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Fan Xiao, Peiqin Liao, Xiaoguang Lu, Jin Wang, Xiu-Qin Dong, Chun-Jiang Wang
Summary: In this study, an Ir-catalyzed asymmetric cascade reaction was successfully developed for the synthesis of chiral oxazinoindolone compounds with high efficiency. The method can be applied to pyrroles and other nitrogen-containing aromatic heterocycles. The reaction pathway was proposed based on preliminary mechanistic investigation. Importantly, the key intermediate for marine alkaloid (+)-agelastatin A can be readily accessed using this methodology.
Article
Chemistry, Multidisciplinary
Qian-Yi Wang, Teng-Fei Liu, Li-Feng Chu, Yun Yao, Chong-Dao Lu
Summary: In the presence of a chiral spiro phosphoric acid catalyst, the asymmetric reaction of disubstituted ketenes with N-H pyrroles occurred to afford enantioenriched C-acylated pyrroles bearing alpha-stereogenic carbon centres. This reaction represents a rare example of catalytic asymmetric reaction of ketenes with carbon-based nucleophiles, with significant research implications.
CHEMICAL COMMUNICATIONS
(2021)
Article
Biochemistry & Molecular Biology
Mohammad Shahidul Islam, Abdullah Saleh Alammari, Assem Barakat, Saeed Alshahrani, Matti Haukka, Abdullah Mohammed Al-Majid
Summary: Five new C-2-symmetric chiral ligands were synthesized from enantiopure amino alcohols, and used for Friedel-Crafts asymmetric alkylation. The bis(oxazolinyl)thiophene ligands showed higher efficiency in inducing asymmetric alkylation compared to bis(imidazolinyl)thiophene analogues.
Article
Chemistry, Organic
Jianguo Yang, Saimei Liu, Jing Gui, Daokai Xiong, Jinshan Li, Zhiming Wang, Jun Ren
Summary: A highly selective hydroxyalkylation of aniline derivatives with arylglyoxal hydrates has been achieved using HFIP as a catalyst. The reaction provides efficient synthesis of various N,N-dialkylanilines and their derivatives with alpha-hydroxy carbonyl units under mild conditions. The method has shown great synthetic potential by enabling the facile synthesis of several structurally interesting molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Weizhi Gu, Jindong Li, Kuiliang Li, Qi Sun, Tong Li, Zhenggen Zha, Zhiyong Wang
Summary: An asymmetric Mannich reaction of 2-fluoroindanone with ketimine was developed using a chiral copper complex catalyst, resulting in the formation of a chiral tetrahedral center containing fluorine. The reaction yielded a series of fi-fluoroamine derivatives in excellent yields (73-94%) with high diastereoselectivities (>99:1 dr) and enantioselectivities (89-99%). Density functional theory calculations supported the proposed transition state.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jia-Qi Wu, Xin-Yuan Wu, Jian-Mei Lu, Qian Shi, Li-Xiong Shao
Summary: In this study, a novel La(III)-based two-dimensional metal-organic framework was synthesized and used as an efficient Lewis acid catalyst for the Friedel-Crafts alkylation reaction. The catalyst exhibited a unique structure, good stability and catalytic activity in acidic and basic environments.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Review
Chemistry, Applied
Daniel Gavina, Marcos Escolano, Javier Torres, Gloria Alzuet-Pina, Maria Sanchez-Rosello, Carlos del Pozo
Summary: Substituted and annulated pyrroles containing chiral centers can be accessed through organocatalytic enantioselective Friedel-Crafts alkylation (FCA) reaction. These compounds are interesting due to their natural occurrence and diverse biological activities. In the past two decades, significant synthetic efforts have been made to develop asymmetric transformations involving pyrroles in the FCA reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Nicolas Zeidan, Sergiu Bicic, Robert J. Mayer, David Leboeuf, Joseph Moran
Summary: This study demonstrates that HFIP greatly expands the scope of the Bronsted acid-catalyzed hydroarylation of enamides, and acts as a slow-release reservoir for the key cationic intermediate. The reaction is fast and practical, and can prevent the oligomerization of the substrate.
Article
Chemistry, Organic
Kodai Saito, Hiromitsu Miyashita, Yui Ito, Masahiro Yamanaka, Takahiko Akiyama
Article
Chemistry, Physical
Tatsuhiro Uchikura, Riku Suzuki, Yusuke Suda, Takahiko Akiyama
Article
Chemistry, Organic
Tatsuhiro Uchikura, Nanami Kamiyama, Taisuke Ishikawa, Takahiko Akiyama
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Tatsuhiro Uchikura, Sosuke Yokohama, Mona Murakami, Takahiko Akiyama
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Physical
Tatsuhiro Uchikura, Nanami Kamiyama, Toshiki Mouri, Takahiko Akiyama
Summary: A visible-light-driven enantioselective radical addition to imines was developed by directly exciting a chiral phosphoric acid-imine complex. Chiral amine products were obtained with high enantioselectivities using benzothiazolines as the radical precursors (up to 98% ee). Mechanistic studies revealed the photoredox activities of the chiral phosphoric acid-imine complex in oxidizing benzothiazolines.
Article
Chemistry, Organic
Tatsuhiro Uchikura, Kureha Aruga, Riku Suzuki, Takahiko Akiyama
Summary: In this study, an enantioselective Friedel-Crafts alkylation reaction was developed using chiral phosphoric acid as the catalyst to react N-unprotected alkynyl trifluoromethyl ketimines with pyrroles, resulting in the synthesis of chiral primary alpha-trifluoromethyl-alpha-(2-pyrrolyl)propargyl-amines with high enantioselectivity. The alkynyl group of the adducts can be transformed without a loss of optical purity, leading to optically active alpha-trifluoromethylated amines bearing various substituents.
Article
Chemistry, Organic
Tatsuhiro Uchikura, Kazushi Tsubono, Yurina Hara, Takahiko Akiyama
Summary: This study reports a dual-role EDA-SET/HAT photoreaction system for carbon-carbon bond formation using a phenol catalyst and aryl iodide. Irradiation of the EDA complex with visible light generates an aryl radical, which abstracts a hydrogen atom from an sp3 carbon to form an alkyl radical.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Tatsuhiro Uchikura, Haruka Nakamura, Hinata Sakai, Takahiko Akiyama
Summary: An efficient and widely applicable silyl radical addition reaction was developed using 2-silylated dihydroquinazolinone derivatives under photocatalytic conditions. Electron-deficient alkenes and styrene derivatives underwent hydrosilylation to give addition products in good to high yields. Mechanistic studies revealed that the photocatalyst functioned as an energy transfer catalyst rather than a photoredox catalyst.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Tatsuhiro Uchikura, Irene Sanchez-Sordo, Tatsuhiko Yoshimura, Yudai Makino, Hiroto Osakabe, Takahiko Akiyama
Summary: We have developed a chiral phosphoric acid-catalyzed enantioselective Friedel-Crafts alkylation reaction between pyrroles and indolylmethanols. Wide substrate scope was observed, and a chiral all-carbon quaternary center was constructed at the 3 position of indoles in high yields with high to excellent enantioselectivities (up to 99% ee).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ken Yamanomoto, Tadachika Matsudaira, Takahiko Akiyama
Summary: We have developed a straightforward method for the synthesis of a-hydroxyamino ketones by utilizing the benzoylation reaction under organophotocatalysis. The reaction proceeds through a benzoyl radical addition to nitrone, and benzothiazoline is found to be a more suitable radical precursor than Hantzsch ester.
Article
Chemistry, Multidisciplinary
Tatsuhiro Uchikura, Sotaro Kato, Yudai Makino, Megumi J. J. Fujikawa, Masahiro Yamanaka, Takahiko Akiyama
Summary: Desymmetrization is a crucial technique for synthesizing chiral compounds, especially chiral biaryls. This study presents an enantioselective synthesis of axially chiral biaryls through desymmetrization using chiral palladium phosphate as the catalyst for C(sp(3))-H activation. Mechanistic investigations reveal that C-H activation plays a crucial role in determining the rate and enantiomeric selectivity. To the best of our knowledge, this is the first report on the asymmetric desymmetrization of axially chiral compounds via C(sp(3))-H activation.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Ken Yamanomoto, Kota Yamamoto, Satoshi Yoshida, Sota Sato, Takahiko Akiyama
Summary: Quinoline and indole are important core structures, and atropisomeric biaryls consisting of quinoline and indole have unique axially chiral structures. We successfully synthesized 3-(N-indolyl)quinolines with both C-N axial chirality and carbon central chirality, exhibiting high selectivity and good yields.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Tatsuhiro Uchikura, Kazuki Takahashi, Tatsushi Oishi, Takahiko Akiyama
Summary: In this study, an enantioselective intermolecular [2 + 2] photocyclization of alkenyl 2-pyrrolyl ketones using a chiral phosphoric acid was reported. The method allows for the synthesis of cyclobutanes with high enantioselectivity (up to 98% ee). UV-Vis spectra showed a bathochromic shift effect upon mixing the alkenyl 2-pyrrolyl ketones and the chiral phosphoric acid. Non-linear correlation between the ee of the catalyst and the ee of the cycloadduct suggests the formation of a dimer complex between both substrates and the chiral phosphoric acid before photocycloaddition.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Tatsuhiro Uchikura, Yurina Hara, Kazushi Tsubono, Takahiko Akiyama
Summary: This study introduces a visible-light-driven synthesis of sulfides without the use of transition metals and strong oxidants. The reaction involves the excitation of an electron donor-acceptor complex between a thiolate and an aryl halide, followed by hydrogen atom transfer from an alkane to the generated aryl radical.
ACS ORGANIC & INORGANIC AU
(2021)
Article
Chemistry, Multidisciplinary
Tatsuhiro Uchikura, Yurina Hara, Kazushi Tsubono, Takahiko Akiyama
Summary: This paper presents a visible-light-driven synthesis of sulfides without the use of transition metals and strong oxidants. The reaction involves an electron donor-acceptor complex between a thiolate and an aryl halide, followed by a hydrogen atom transfer from an alkane to the generated aryl radical.
ACS ORGANIC & INORGANIC AU
(2021)
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)
