Article
Chemistry, Organic
A'lvaro Gutierrez-Bonet, Wenbin Liu
Summary: Using alpha-fluoroalkyl or fluorobenzyl radicals generated from easily accessible alpha-fluorocarboxylic acids, we achieved the rapid synthesis of fluorine-containing building blocks through Giese-type addition reactions. This method allows for the preparation of mono- and difluorinated Michael addition adducts as well as unnatural fluorinated amino acids under mild reaction conditions.
Article
Chemistry, Organic
Shuang Yang, Shoujie Shi, Yuhang Chen, Zhenhua Ding
Summary: The regiodivergent synthesis of dihydroxazines and fluorinated oxazepanes from allylaminoethanol using a hypervalent fluoroiodane was investigated. The reaction proceeded under mild conditions and yielded moderate to good products, with selectivity controlled by the substituents of the allylaminoethanol.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yunfei Tian, Luping Zheng, Zhiqiang Wang, Zejiang Li, Weijun Fu
Summary: A new strategy for electrochemical oxidative difluoroethylation using sodium difluoroethylsulfinate (DFES-Na) has been reported, which successfully generates difluoroethyl radical for the first time. This method allows the quick synthesis of valuable difluoroethylated azaheterocycles, including oxindoles and isoquinoline-1,3-diones, in moderate to good yields. The electrochemical cyclopropyldifluoromethylation of N-arylacrylamides also shows good results using this strategy. Furthermore, radical capture and cyclic voltammetry (CV) experiments were carried out to confirm the proposed mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yunfei Tian, Luping Zheng, Zhiqiang Wang, Zejiang Li, Weijun Fu
Summary: A new strategy of electrochemical oxidative difluoroethylation using sodium difluoroethylsulfinate (DFES-Na) has been reported for generating difluoroethyl radical. This method provides a quick access to valuable difluoroethylated azaheterocycles including oxindoles and isoquinoline-1,3-diones via radical tandem difluoroethylation/cyclization with moderate to good yields. The electrochemical cyclopropyldifluoromethylation of N-arylacrylamides also showed good results using this strategy. Furthermore, radical capture and cyclic voltammetry (CV) experiments were conducted to determine the proposed mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Koki Maruno, Kiyoteru Niina, Osamu Nagata, Norio Shibata
Summary: In this study, a fully fluorinated motif with high lipophilicity and polarity was introduced, which can connect two independent groups via three continuous atoms. The motif was synthesized through a cycloaddition reaction.
Article
Multidisciplinary Sciences
Ting-Bi Hua, Cheng-Xiong Liu, Wei-Min Hu, Long Wang, Qing-Qing Yang
Summary: An efficient [4+1] annulation method has been developed for the synthesis of biologically interesting isoxazoline derivatives via in situ generation of nitrosoalkenes under mild basic reaction conditions, providing good to excellent yields.
SCIENTIFIC REPORTS
(2021)
Article
Chemistry, Multidisciplinary
Yuno Oe, Ryuhei Yoshida, Airi Tanaka, Akiya Adachi, Yuichiro Ishibashi, Takashi Okazoe, Kohsuke Aikawa, Takuya Hashimoto
Summary: This study reports the development of a novel N-fluorinated imide (NFC) as a synthetic handle for the one-step derivatization to amines, sulfonamides, and sulfamides. It also demonstrates the superior reactivity of NFC in copper-catalyzed imidation of benzene derivatives and imidocyanation of aliphatic alkenes, overcoming the limitations of NFSI-mediated reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Christian Wulkesch, Constantin Czekelius
Summary: The study highlights a mild, operationally simple, and inexpensive photocatalytic perfluoroalkenylation reaction for the direct synthesis of tetrasubstituted, highly electron-deficient enals from aldehydes. The one-step reaction is tolerant to various functional groups and can be applied to a wide range of substrates, with product yields ranging from 52-84%.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Manas Mondal, Debajyoti Saha, Amit Saha
Summary: The synthesis of phenacyl-bis(dithiocarbamates) is achieved through a metal-free trifunctionalization reaction of phenylacetylene systems. This reaction involves oxidative bromination of phenyl acetylene followed by nucleophilic substitution with freshly prepared dithiocarbamate salt. Various gem-bis(dithiocarbamates) are prepared using different secondary amines and phenylacetylene systems with different substituents.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Polymer Science
Alexandrina Nan, Teodora Radu, Xenia Filip, Irina Kacso, Niculina Daniela Hadade, Fran Nekvapil, Maria Miclaus
Summary: Recently, there has been great interest in synthesizing polymers with fluorine atoms. This work presents the synthesis, characterization, and properties of a new fluorinated aromatic polyester, Poly(fluoromandelic acid) (PFMA). The polymer chain of PFMA contains multiple fluorine atoms and exhibits high hydrophobicity and good thermal stability.
Article
Biochemistry & Molecular Biology
Sergey A. Usachev, Diana Nigamatova, Daria K. Mysik, Nikita A. Naumov, Dmitrii L. Obydennov, Vyacheslav Y. Sosnovskikh
Summary: A convenient and general method for the direct synthesis of 2-aryl-6-(trifluoromethyl)-4-pyrones and 2-aryl-5-bromo-6-(trifluoromethyl)-4-pyrones has been developed through a one-pot oxidative cyclization approach. This strategy has broad application potential for the preparation of pyrones and their derivatives. The prepared pyrones can be used for the synthesis of biologically important azaheterocycles containing CF3 group.
Article
Chemistry, Multidisciplinary
Benjamin R. Boswell, Carl M. F. Mansson, Jordan M. Cox, Zexin Jin, Joseph A. H. Romaniuk, Kurt P. Lindquist, Lynette Cegelski, Yan Xia, Steven A. Lopez, Noah Z. Burns
Summary: Fluorinated polyacetylene, a long-sought-after air-stable polymer, has been successfully synthesized through a mechanochemical unzipping strategy. Polymer mechanochemistry is a valuable tool for accessing new materials on a preparative scale, especially those inaccessible by other means. This work demonstrates the potential of polymer mechanochemistry in the scalable synthesis of novel materials.
Article
Chemistry, Organic
Zhe Meng, Xiaoyu Zhang, Min Shi
Summary: A novel fluoroalkylation and cycloisomerization cascade reaction of ene-VDCP with ethyl iododifluoroacetate or perfluoroalkyl iodide under visible-light irradiation is reported in this study, providing the desired fluorinated cyclization products in moderate to good yields and showing good functional group tolerance. Mechanistic investigations suggest the presence of a radical chain process in this reaction.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Xiaoman Li, Jiawei Huang, Liang Xu, Ping Liu, Yu Wei
Summary: In this study, a tetrabutylammonium tribromide-mediated three-component reaction of alkenes, diselenides, and sulfoximines was established, providing a direct and metal-free access to diverse beta-arylseleno sulfoximine derivatives. This regioselective sulfoximido-selenization protocol proceeds efficiently under mild and ambient conditions with generally good yields. The strategy is characterized by step and atom economy, practicability, a broad substrate scope, and gram-scale synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Caocao Sun, Yuqiang Li, Guoyin Yin
Summary: We report a modular catalytic method for the enantioselective synthesis of chiral allylboronates from abundant feedstock chemicals. This method shows advantages in terms of the use of inexpensive catalyst, mild reaction conditions, wide substrate scope, scalability, and practicality. The utility of the method is demonstrated by the rapid synthesis of key intermediates of complex drug molecules. Mechanistic studies reveal the regioselective nature of beta-H elimination and the enantio-determining step involving reversible homolysis and convergance to a lower energy pre-reductive elimination intermediate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Yubao Wang, Michael Begley, Qing Li, Hai-Tsang Huang, Ana Lako, Michael J. Eck, Nathanael S. Gray, Timothy J. Mitchison, Lewis C. Cantley, Jean J. Zhao
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2016)
Article
Biology
Yaara Zwang, Oliver Jonas, Casandra Chen, Mikael L. Rinne, John G. Doench, Federica Piccioni, Li Tan, Hai-Tsang Huang, Jinhua Wang, Young Jin Ham, Joyce O'Connell, Patrick Bhola, Mihir Doshi, Matthew Whitman, Michael Cima, Anthony Letai, David E. Root, Robert S. Langer, Nathanael Gray, William C. Hahn
Article
Biology
Hai-Tsang Huang, Hyuk-Soo Seo, Tinghu Zhang, Yubao Wang, Baishan Jiang, Qing Li, Dennis L. Buckley, Behnam Nabet, Justin M. Roberts, Joshiawa Paulk, Shiva Dastjerdi, Georg E. Winter, Hilary McLauchlan, Jennifer Moran, James E. Bradner, Michael J. Eck, Sirano Dhe-Paganon, Jean J. Zhao, Nathanael S. Gray
Article
Biochemistry & Molecular Biology
Sourav Banerjee, Sara J. Buhrlage, Hai-Tsang Huang, Xianming Deng, Wenjun Zhou, Jinhua Wang, Ryan Traynor, Alan R. Prescott, Dario R. Alessi, Nathanael S. Gray
BIOCHEMICAL JOURNAL
(2014)
Article
Biochemical Research Methods
Patrick D. DeArmond, Graham M. West, Hai-Tsang Huang, Michael C. Fitzgerald
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
(2011)
Article
Multidisciplinary Sciences
Wei-Chien Yuan, Brian Pepe-Mooney, Giorgio G. Galli, Michael T. Dill, Hai-Tsang Huang, Mingfeng Hao, Yumeng Wang, Han Liang, Raffaele A. Calogero, Fernando D. Camargo
NATURE COMMUNICATIONS
(2018)
Article
Biology
M. Catarina Silva, Fleur M. Ferguson, Quan Cai, Katherine A. Donovan, Ghata Nandi, Debasis Patnaik, Tinghu Zhang, Hai-Tsang Huang, Diane E. Lucente, Bradford C. Dickerson, Timothy J. Mitchison, Eric S. Fischer, Nathanael S. Gray, Stephen J. Haggarty
Article
Biochemistry & Molecular Biology
Hai-Tsang Huang, Dennis Dobrovolsky, Joshiawa Paulk, Guang Yang, Ellen L. Weisberg, Zainab M. Doctor, Dennis L. Buckley, Joong-Heui Cho, Eunhwa Ko, Jaebong Jang, Kun Shi, Hwan Geun Choi, James D. Griffin, Ying Li, Steven P. Treon, Eric S. Fischer, James E. Bradner, Li Tan, Nathanael S. Gray
CELL CHEMICAL BIOLOGY
(2018)
