Article
Chemistry, Multidisciplinary
Jonas Wolfs, Roman Nickisch, Lisa Wanner, Michael A. R. Meier
Summary: The study introduces a novel concept combining tandem catalysis and cellulose derivatization, utilizing a single catalyst for three transformations in a DMSO/DBU/CO2 switchable solvent system. Results show that the tandem reaction approach is more beneficial in terms of efficiency and sustainability compared to stepwise synthesis. By analyzing the obtained products, researchers controlled the degree of substitution of O-cellulose thiocarbamates.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Satheesh Borra, Hun Young Kim, Kyungsoo Oh
Summary: A one-pot tandem approach to [1,2,3]triazolo[1,5-a]quinolines was developed from (E)-s-chlorovinyl ketones and 2-azidoaryl carbonyls using a sequence of alpha-vinyl aldol and azide- alkyne cycloaddition reactions. The intramolecular azide-alkyne cycloaddition of allenol intermediates was promoted by NEt3 and nickel catalysts. The [1,2,3]triazolo[1,5-a]quinolines are important precursors to alpha-diazoimines and can provide valuable heterocyclic compounds through denitrogenative transformations.
Article
Chemistry, Organic
Zhegao Ye, Ziran Lei, Xiaodong Ye, Liejin Zhou, Yanan Wang, Zheliang Yuan, Feng Gao, Robert Britton
Summary: A mild and general method for trifluoromethylthiolation of aldehydes using N-trifluoromethylthiosaccharin and sodium decatungstate as the photocatalyst has been reported. Electron-rich aldehydes show better reactivity, while good selectivity is observed for the trifluoromethylthiolation of aldehydic C-H bonds. Preliminary mechanistic studies suggest a free radical process is involved.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Eren Esen, Pauline Haedinger, Michael A. R. Meier
Summary: The study introduced a sustainable synthesis method for fatty acid cellulose esters, showcasing how varying reaction parameters led to the generation of different substitution degrees. The modification process through thiol-ene reaction further allowed for the tuning of structure and properties of the cellulose derivatives. Mechanical testing of films produced from the samples revealed that the DS and thiol type used for modification impacted the materials' performance. Additionally, contact angle measurements indicated an increase in surface hydrophobicity for the thiol-ene-modified samples.
Article
Chemistry, Multidisciplinary
Tingting Feng, Canxiang Liu, Zhen Wu, Xinxin Wu, Chen Zhu
Summary: This report describes a manganese-catalyzed radical [3 + 2] cyclization reaction of cyclopropanols and oxime ethers, providing an efficient approach for the synthesis of structurally diverse 1-pyrrolines.
Article
Chemistry, Multidisciplinary
Vani Singhania, Margery Cortes-Clerget, Jade Dussart-Gautheret, Bhornrawin Akkachairin, Julie Yu, Nnamdi Akporji, Fabrice Gallou, Bruce H. Lipshutz
Summary: In an aqueous micellar medium, commercially available lipase catalyzes esterification with high selectivity in the absence of any co-factors, aided by only 2% designer surfactant TPGS-750-M. An unexpected finding shows that the simple additive PhCF3 can significantly expand the range of usable acid/alcohol combinations. This allows for multiple chemo- and bio-catalyzed 1-pot, multi-step reactions to be performed in water.
Article
Chemistry, Organic
Yukun Chen, Xiaoxiang Xi, Weiming Yuan
Summary: A photoinduced nickel-catalyzed reductive acyl-coupling reaction has been developed, enabling the synthesis of sterically bulky alpha-tertiary ketones. The reaction does not require an exogenous photocatalyst or a metal reductant, and various unstrained tertiary acyl electrophiles can be coupled with alkyl radicals under mild conditions, leading to the formation of all carbon quaternary aliphatic ketones, including alpha-tertiary amino ketones.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Qing-Qiang Su, Ruo-Nan Wang, Yong-Zheng Lv, Ya-Xin Fan, Shan Li, Hong-Li Huang, Ji-Yuan Du
Summary: This study presents a one-pot cycloaddition reaction of ethynyl indoloxazolidones with 1,3-cyclohexanediones enabled by copper catalysis, leading to a series of functionalized furan derivatives in good yields. The method demonstrates mild reaction conditions, high efficiency, and wide substrate scope.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Guanghui Wang, Jian Jia, Gang Liu, Mingwu Yu, Xiaoxiao Chu, Xiguang Liu, Ximei Zhao
Summary: An efficient one-step synthesis of 2-acylquinolines using a copper-catalyzed tandem reaction has been developed, providing a practical tool for synthetic and pharmaceutical chemists. The method avoids multi-step operation and the use of highly toxic cyanides, with various products obtained with perfect regioselectivity in moderate to good yields. The potential synthetic utility of this method is exemplified by a large-scale experiment and synthetic transformation of the products.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Donghui Guo, Qiupeng Peng, Bei Zhang, Jian Wang
Summary: The novel method described in this report allows for the atroposelective generation of axially chiral amino esters using hemiaminals formed in situ, with a wide substrate scope, good functional group tolerance, and rapid assembly of axially chiral amino esters with high enantioselectivities in good to high yields.
Article
Multidisciplinary Sciences
Shi-Chao Ren, Xing Yang, Bivas Mondal, Chengli Mou, Weiyi Tian, Zhichao Jin, Yonggui Robin Chi
Summary: This study reports a decarboxylative radical coupling of carboxylic acids and acyl imidazoles catalyzed by an N-heterocyclic carbene and photocatalyst. The carboxylic acids serve as direct radical precursors, and suitable acyl imidazoles can also be generated in situby a reaction with CDI. The method is extended to three-component coupling by using alkenes as a third coupling partner via a radical relay process. The mild reaction conditions, simplicity, and use of easily available starting materials make this method a powerful strategy for constructing complex ketones and modifying natural products and medicines.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Kai-Rui Feng, Yun-Xuan Tan, Wenbo Ye, Yi-Fan Wang, Zhi-Tao He, Ping Tian, Guo-Qiang Lin
Summary: The study successfully achieved Cu-catalyzed asymmetric carboboration of cyclohexadienone-tethered allenes, resulting in cis-bicyclic frameworks with high enantioselectivities. Further conjugate borylation improved the overall enantioselectivity, and one-pot preparation of highly enantioenriched tricyclo[5.2.2.0(4,9)]undecanes was developed.
Article
Chemistry, Organic
Dina Scarpi, Nunzia Favale, Ernesto G. Occhiato
Summary: A highly efficient method for the one-pot synthesis of ring-fused 5-hydrazino-2-cyclopentenone derivatives is achieved through the catalysis of gold(I). Suitable enynyl acetates are mixed with a dialkylazodicarboxylate in the presence of a gold(I) catalyst to undergo cycloisomerization, hetero-Diels-Alder, and ring-opening reactions, resulting in the target compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Sanju Das, Sushanta Kumar Parida, Tanumoy Mandal, Sudhir Kumar Hota, Lisa Roy, Suman De Sarkar, Sandip Murarka
Summary: An organophotoredox-catalyzed reduction/addition/oxidation cascade of N-protected maleimides and N-(acyloxy)phthalimides has been reported, involving the Giese-type addition of aryloxy-alkyl radicals on N-protected maleimides and a successive oxidation to allow Z-alkenylation of the N-substituted pyrrolidine-2,5-dione motif through a formal translocation of the maleimide double bond.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Zhen Yao, Ji Yang, Zhenli Luo, Jianhan Ye, Jiahong Han, Xin Zhang, Lijin Xu, Peng Wang, Qian Shi
Summary: This study presents a tandem one-pot regioselective synthesis method under visible-light photocatalysis, providing a straightforward approach for the synthesis of C4-difluoroalkylated phthalazin-1(2H)-ones with broad substrate scope and wide functional group tolerance.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Satoshi Umezu, Gabriel dos Passos Gomes, Tatsuro Yoshinaga, Mikei Sakae, Kenji Matsumoto, Takayuki Iwata, Igor Alabugin, Mitsuru Shindo
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Organic
Shigenobu Fujimoto, Kenji Matsumoto, Takayuki Iwata, Mitsuru Shindo
TETRAHEDRON LETTERS
(2017)
Article
Chemistry, Multidisciplinary
Satoshi Fujita, Keisuke Nishikawa, Takayuki Iwata, Taishi Tomiyama, Hiroshi Ikenaga, Kenji Matsumoto, Mitsuru Shindo
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Tatsuro Yoshinaga, Takumi Fujiwara, Takayuki Iwata, Mitsuru Shindo
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Organic
Jun Sun, Toshiya Yoshiiwa, Takayuki Iwata, Mitsuru Shindo
Article
Chemistry, Multidisciplinary
Takayuki Iwata, Mizuki Hyodo, Takuto Fukami, Yoshihito Shiota, Kazunari Yoshizawa, Mitsuru Shindo
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Organic
Kenji Matsumoto, Yasunori Toubaru, Shohei Tachikawa, Ayaka Miki, Kentaro Sakai, Syota Koroki, Tsukasa Hirokane, Mitsuru Shindo, Masahiro Yoshida
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Genetics & Heredity
Samy Carbonnel, Salar Torabi, Maximilian Griesmann, Elias Bleek, Yuhong Tang, Stefan Buchka, Veronica Basso, Mitsuru Shindo, Francois-Didier Boyer, Trevor L. Wang, Michael Udvardi, Mark T. Waters, Caroline Gutjahr
Article
Chemistry, Multidisciplinary
Takayuki Iwata, Satoru Kumagai, Tatsuro Yoshinaga, Masato Hanada, Yoshihito Shiota, Kazunari Yoshizawa, Mitsuru Shindo
Summary: This paper reports a Pd-catalyzed domino reaction of 1,8,13-tribromo-9-methoxytriptycenes and reveals the reaction mechanism. The study shows that a single Pd catalyst can simultaneously participate in multiple distinct reaction processes.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Takayuki Iwata, Ryusei Kawano, Takuto Fukami, Mitsuru Shindo
Summary: The triptycene scaffold can be ring-opened through a retro-Friedel-Crafts-type reaction under acidic conditions, yielding the corresponding anthrone product. 9-Hydroxytriptycenes and unsubstituted triptycene undergo ring-opening reaction in strongly acidic conditions, such as with TfOH. The investigation of the substitution effect reveals that an electron-donating group on the arene moiety allows the reaction to proceed in the presence of a weaker acid, such as TFA. Additionally, the reaction has proven successful for the synthesis of tetracene.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Editorial Material
Chemistry, Multidisciplinary
Takayuki Iwata, Ryusei Kawano, Takuto Fukami, Mitsuru Shindo
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Mitsuru Shindo, Takayuki Iwata
Summary: This paper describes the ynolate-initiated cycloaddition reaction to form a variety of carbocycles and heterocycles. Ynolates have the ability to achieve double addition and can perform formal [n+1]-type annulations, demonstrating their high-energy performance. The synthetic applications of these methods, including natural products synthesis, are discussed as well.
Article
Chemistry, Organic
Takayuki Iwata, Mizuki Hyodo, Takumi Fujiwara, Ryusei Kawano, Leah Kuhn, Igor V. Alabugin, Mitsuru Shindo
Summary: The first regioselective addition reactions to 3-trifluoromethylbenzyne are reported. High regioselectivity was achieved in the triple cycloaddition reaction of ynolates and the Diels-Alder reaction of anthranoxides with the benzyne, resulting in the synthesis of triptycenes with different trifluoromethyl substitution patterns.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Takayuki Iwata, Mizuki Hyodo, Ryusei Kawano, Mitsuru Shindo
Summary: A highly efficient method for synthesizing higher-order iptycenes using an ambident anthracene building block is presented. The method provides systematic synthesis of higher-order iptycenes, including the longest-chain iptycene synthesized so far. X-ray crystallography reveals interesting structures of these iptycenes, with solvent molecules filling the cavities and forming a honeycomb structure.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Shuso Takeda, Masayo Hirao-Suzuki, Mitsuru Shindo, Hironori Aramaki
Summary: This study demonstrates that (-)-xanthatin is able to kill mammospheres of breast cancer CSCs, indicating a potential anti-proliferative mechanism.
CURRENT ISSUES IN MOLECULAR BIOLOGY
(2022)
