Article
Chemistry, Multidisciplinary
Haopeng Xu, Chao Pi, Yangjie Wu, Xiuling Cui
Summary: An efficient multi-component reaction has been developed for the synthesis of 2,3-disubstituted tetrahydrofurans in a one-pot manner, providing a wide array of alpha-indole-beta-sulfonyl tetrahydrofurans in good yields with excellent selectivity, while avoiding the use of various additives and transition metals as catalysts.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Alena Budinska, Helma Wennemers
Summary: This article presents a mild and efficient organocatalytic method for the stereoselective synthesis of chiral triflones using alpha-aryl vinyl triflones, previously unexplored in asymmetric synthesis. The products can be easily derivatized into disubstituted delta-sultones, gamma-lactones, and pyrrolidine heterocycles, highlighting their synthetic versatility.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Di An, Jingjing Sang, Rui Hu, Jichao Chen, Li Feng, Weidong Rao
Summary: A new synthetic approach for the synthesis of 2-phosphoryl-3-monofluorovinylindoles via cascade regioselective dehydrative phosphorylation/stereoselective defluorination is described. The reaction can be scaled-up without the need for column chromatography purification.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Jun-Li Li, Xiaoying Niu, Yi-Fan Song, Jian-Long Du, Shigang Shen, Xiu-Long Yang
Summary: A single cobaloxime-catalyzed acceptorless dehydrogenative cyclization method was developed for the synthesis of 1,3-dicarbonyl compounds with quinone and benzene rings. This method does not require bases or oxidants, offering a highly atom-economical strategy.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Satawat Tongdee, Duo Wei, Jiajun Wu, Chakkrit Netkaew, Christophe Darcel
Summary: An efficient method for the preparation of lactams from omega-amino fatty acids under hydrosilylation is described. Various lactams were selectively synthesized in moderate to excellent yields with good functional group tolerance, without the need for a metallic based catalyst.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Engineering, Environmental
Morvarid Najjar, Mohammad Ali Nasseri, Majid Darroudi, Ali Allahresani
Summary: A novel heterogeneous catalyst prepared from magnetic nanoparticles coated with silicate modified with graphene quantum dot-copper (GQD/Cu) was highly efficient in multicomponent reactions, leading to good-to-excellent yields of synthesized derivatives.
JOURNAL OF ENVIRONMENTAL CHEMICAL ENGINEERING
(2022)
Article
Chemistry, Organic
Aline A. N. de Souza, Aloisio de A. Bartolomeu, Timothy J. Brocksom, Timothy Noel, Kleber T. de Oliveira
Summary: The electrochemical sulfenylation reaction was investigated in both batch and continuous flow regimes, with quaternary ammonium salts identified as the best mediators. The tolerance of Boc-cysteine to the reaction protocol was noted, increasing its relevance. The methodology was found to be scalable in both batch and continuous flow conditions, offering potential for further studies involving important functional groups in organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yu-Ming Yang, Wei Yan, Han-Wei Hu, Yimin Luo, Zhen-Yu Tang, Zhuangzhu Luo
Summary: This method involves the green and efficient visible-light induced functionalization of anilines under mild conditions, using non-toxic diacetyl as the photosensitizer and acetylating reagent, and water as the solvent. It provides a valuable approach in organic synthesis with environmentally friendly conditions, simple operation, wide substrate scope, and functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kusum Ucheniya, Amreen Chouhan, Lalit Yadav, Pooja Kumari Jat, Satpal Singh Badsara
Summary: We report a mild, scalable, electricity-promoted protocol for the cross coupling of allylic iodides and disulfides/diselenides to form C-S/Se bonds without the need for transition metals, bases, or oxidants. Different stereochemically diverse allylic iodides gave regio- and stereoselective thioethers in good yields. This strategy provides a sustainable and promising approach for the synthesis of allylic thioethers with yields ranging from 38% to 80%. Additionally, this protocol serves as a synthetic platform for the synthesis of allylic selenoethers. The involvement of a single-electron transfer radical pathway was confirmed through radical scavenger experiments and cyclic voltammetry data.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shuang Wang, Jun-Jie Lin, Xin Cui, Jing-Peng Li, Chao Huang
Summary: A one-pot method has been developed for the selective synthesis of two isomers without a catalyst, forming multiple chemical bonds in mild conditions with high atom economy. The selectivity is controlled by thermodynamics and kinetics, with discussions on the reasons for the transformation of the two structures.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Mohammad Pirbaba, Rezvan Kardooni, Ali Reza Kiasat, Mohammad Sabaeian
Summary: Solar radiation-assisted green approach was developed for the chemoselective synthesis of 3-alkylated indoles via Yonemitsu-type condensation under catalyst-free conditions. The desired products were formed by one-pot three-component reaction using non-volatile solvent and renewable energy resources. The approach showed good scope and generality, and increased economic and environmental effectiveness.
ARABIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Akhil K. Dubey, Raghunath Chowdhury
Summary: A new method for the enantioselective 1,4-conjugate addition of nitromethane to beta-silyl alpha,beta-unsaturated carbonyl compounds catalyzed by bifunctional squaramide catalysts has been developed. This methodology offers both enantiomers of beta-silyl nitroalkanes in good to excellent yields and enantioselectivities under solvent-free conditions at room temperature. Control experiments revealed the crucial role of a beta-silyl group in enones for high reactivity under the optimized reaction conditions.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Pouria Patoghi, Ali Sadatnabi, Davood Nematollahi
Summary: In this study, a new convergent paired electro-organic synthesis method for sulfonamide derivatives was introduced, which follows the principles of green chemistry and does not require catalysts, oxidants, halogens, or amines. Instead of using toxic amine compounds, an innovative mechanism based on the reduction of nitro compounds and in-situ production of amine compounds was used. The mechanism involves cathodic reduction of nitro compounds to hydroxylamine compounds and anodic oxidation of hydroxylamine compounds to nitroso compounds.
SCIENTIFIC REPORTS
(2023)
Article
Chemistry, Organic
Yuxing Zhang, Sha Du, Tao Yang, Fengyan Jin, Jingyi Zhou, Banpeng Cao, Zhi-Jie Mao, Xian-Rong Song, Qiang Xiao
Summary: An environmentally-friendly approach for synthesizing tetrasubstituted allenyl organothiophosphates with highly congested carbon centers has been developed. The method involves an in situ dehydrative cross-coupling reaction using easily prepared propargylic alcohols and phosphorothioic acids, with water as the only by-product. The reaction proceeds in the presence of (EtO)2P(O)SH without the need for ligands, additives, or additional acid promoters. The method is compatible with propargylic alcohols bearing various electron-rich and electron-withdrawing groups, affording moderate to excellent yields under mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Applied
Kanokwan Jaithum, Jumreang Tummatorn, Bundet Boekfa, Charnsak Thongsornkleeb, Kittipong Chainok, Somsak Ruchirawat
Summary: A method using a silver catalyst and acid for the diastereoselective synthesis of spirocyclic ethers has been developed, showing good yields of 97% and broad substrate applicability. The proposed reaction mechanisms and stereoselectivity outcomes have been investigated using DFT calculation.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Medicinal
Yuji Sumii, Kentaro Kamiya, Takehiko Nakamura, Kenta Tanaka, Takumi Kaji, Junya Mukomura, Naoyuki Kotoku, Masayoshi Arai
Summary: The current treatment for tuberculosis is long and complex due to the ability of Mycobacterium tuberculosis to enter a dormant state. Identifying new compounds with different chemical structures is essential for improving treatment outcomes. This study investigates the structure-activity relationship of a potential anti-tuberculosis compound and successfully develops a probe molecule for detecting its target protein.
Article
Multidisciplinary Sciences
Satoshi Yamanaka, Yuto Horiuchi, Saya Matsuoka, Kohki Kido, Kohei Nishino, Mayaka Maeno, Norio Shibata, Hidetaka Kosako, Tatsuya Sawasaki
Summary: This article introduces a method based on AirID to identify drug-induced neo-substrates through proximity-dependent biotinylation. The study identifies several new CRBN substrates and demonstrates that this method can serve as a general strategy for studying drug-induced protein-protein interactions in cells.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Hiroto Uno, Koki Kawai, Taichi Araki, Motoo Shiro, Norio Shibata
Summary: Gem-difluoromethylene moieties are attractive in medicinal chemistry due to their ability to mimic other more ubiquitous functional groups. A novel asymmetric method for their construction was developed, allowing easy access to chiral 1,3-dioxanes that contain a tetrasubstituted difluoroalkyl stereogenic center. The gem-difluoro substitution pattern promotes the reaction, and various substrates were suitable for this method.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Kentaro Iwaki, Kazuhiro Tanagawa, Soichiro Mori, Koki Maruno, Yuji Sumii, Osamu Nagata, Norio Shibata
Summary: In this study, we reported a metal-free hydration reaction of pyridine-SF4-alkynes under acidic conditions, which synthesized pyridine-SF4-methyl ketones with yields ranging from 59% to 93%. We further demonstrated the synthetic applications of these compounds, including chlorination, NaBH4 reduction, Baeyer-Villiger oxidation, and the generation of enol triflates. These compounds show promise as useful building blocks in the synthesis of a wide range of SF4-containing drug candidates.
Article
Chemistry, Organic
Jun Zhou, Bingyao Jiang, Zhengyu Zhao, Norio Shibata
Summary: A potassium base-mediated defluoroetherification method for aryl and heteroaryl fluorides is reported, which efficiently and safely provides a wide variety of aryl ethers without the use of metal catalysts, specific ligands, and harsh conditions. This method can also be applied to the late-stage etherification of structurally complex fluorides and bioactive alcohols.
Article
Chemistry, Organic
Elizabeth L. Goldstein, Hirokazu Takada, Yuji Sumii, Katsuaki Baba, Brian M. Stoltz
Summary: The synthesis of enantioenriched 2,2-disubstituted pyrrolidines is achieved through asymmetric allylic alkylation and thermal Spino ring contraction reactions. The resulting compounds have potential in the development of new pharmaceutical agents.
Article
Chemistry, Organic
Yuji Sumii, Hiroto Iwasaki, Yamato Fujihira, Elsayed M. Mahmoud, Hiroaki Adachi, Takumi Kagawa, Dominique Cahard, Norio Shibata
Summary: A protocol for the stereodivergent pentafluoroethylation of N-sulfinylimines has been developed using HFC-125 with KHMDS/triglyme. The presence or absence of triglyme enables the selective synthesis of both diastereomers of the pentafluoroethylated amines. This additive-controlled protocol offers a straightforward and cost-effective alternative to the previously reported base-controlled stereodivergent trifluoromethylation using potassium hexamethyldisilazide (KHMDS) versus P4-tBu.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Masahiro Sugiura, Kazuki Ishikawa, Kota Katayama, Yuji Sumii, Rei Abe-Yoshizumi, Satoshi P. Tsunoda, Yuji Furutani, Norio Shibata, Leonid S. Brown, Hideki Kandori
Summary: This study reports a novel photochemical reaction mediated by a microbial rhodopsin, leading to the selective transition from the all-trans to 7-cis form.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Norio Shibata, Dominique Cahard
Summary: From 2000, our two research groups independently and simultaneously designed and developed a novel family of electrophilic fluorinating reagents based on the use of Cinchona alkaloids. The chiral N-fluoro ammonium salts demonstrated the highest efficiency compared to prior art in enantioselective electrophilic fluorination for a wide range of substrates. In this account, we tell our respective stories, how the same idea germinated in our laboratories, the characterization of the chiral reagents, the use in stoichiometric quantity then the development of a catalytic version, the application to the synthesis of chiral fluorinated molecules of pharmaceutical interest, and finally the exploitation of our reagents by other teams and for other applications.
Review
Chemistry, Multidisciplinary
Yuji Sumii, Norio Shibata
Summary: The trifluoromethyl group is a crucial component in drugs and polymers, making the development of trifluoromethylation reactions a significant area of research in organic chemistry. Various methods, including nucleophilic and electrophilic approaches, transition-metal catalysis, photocatalysis, and electrolytic reactions have been developed over the years. Microflow versions of these reactions have shown great potential for industrial applications due to their scalability, safety, and time efficiency. This review discusses the current state of microflow trifluoromethylation, focusing on different trifluoromethylation reagents and techniques such as continuous flow, flow photochemical, microfluidic electrochemical reactions, and large-scale microflow reactions.
Letter
Chemistry, Organic
Elsayed M. Mahmoud, Soichiro Mori, Yuji Sumii, Norio Shibata
Summary: The synthesis of acyl fluorides from carboxylic acids is achieved using Selectfluor mediated by elemental sulfur. A wide range of acyl fluorides can be accessed while avoiding the formation of acid anhydrides. F-19 NMR spectra indicate that the reactive species in this deoxyfluorination reaction are the in situ generated S-8-fluoro-sulfonium cation A and neutral S-8-difluoride A'.
Article
Multidisciplinary Sciences
Jun Zhou, Zhengyu Zhao, Norio Shibata
Summary: Defluorinative cross-coupling between amines and organic fluorides is achieved via a silylboronate-mediated strategy. This method enables the room-temperature cross-coupling of C-F and N-H bonds, avoiding the high energy barriers associated with thermally induced S(N)2 or S(N)1 amination. The selective activation of the C-F bond of organic fluorides by silylboronate is a significant advantage of this transformation.
NATURE COMMUNICATIONS
(2023)
Editorial Material
Chemistry, Multidisciplinary
Norio Shibata, Dinesh Talwar
Summary: The unique properties and applications of fluorine-containing molecules have had significant impact across different scientific fields, from small to large molecules. This special issue provides a comprehensive overview of the state-of-the-art in fluorine chemistry.
Article
Chemistry, Multidisciplinary
Jun Zhou, Zhengyu Zhao, Bingyao Jiang, Katsuhiro Yamamoto, Yuji Sumii, Norio Shibata
Summary: In this study, an efficient silylboronate-mediated cross-coupling reaction of aryl fluorides with arylalkanes was developed under transition-metal-free, room-temperature conditions. The method showed good adaptability to aryl fluorides with a C(sp(2))-F bond and can be extended to other coupling partners with a C(sp(3))-H bond. It provides a practical and convenient approach to obtain di- and triarylalkanes with tertiary or quaternary carbon centers.
