Aryl sulfonyl fluoride synthesis via palladium-catalyzed fluorosulfonylation of aryl thianthrenium salts?
Organic & Biomolecular Chemistry Pub Date: 2023-04-20 DOI: 10.1039/D3OB00462G
Abstract
We developed an efficient palladium-catalyzed fluorosulfonylation reaction of aryl thianthrenium salts to smoothly prepare various aryl sulfonyl fluorides using cheap Na2S2O4 as a convenient sulfonyl source in combination with N-fluorobenzenesulfonimide (NFSI) as an ideal fluorine source under mild reduction conditions. A one-pot synthesis of aryl sulfonyl fluorides starting from various arenes was established as well without the need for separating aryl thianthrenium salts. The practicality of this protocol was demonstrated by gram-scale synthesis, derivatization reactions, and excellent yields.
Recommended Literature
- [1] Evolution of calcium phosphate precipitation in hanging drop vapor diffusion by in situRaman microspectroscopy Gloria Belén Ramírez-Rodríguez,José Manuel Delgado-López,Jaime Gómez-MoralesCrystEngComm, 2013,15, 2206-2212 10.1039/C2CE26556G
- [2] Embedding heteroatoms: an effective approach to create porphyrin-based functional materials Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro OsukaDalton Trans., 2017,46, 13322-13341 10.1039/C7DT02815F
- [3] Fc microparticles can modulate the physical extent and magnitude of complement activity? David White,Sean R. StowellBiomater. Sci., 2017,5, 463-474 10.1039/C6BM00608F
- [4] Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR? Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing XiaNanoscale, 2020,12, 20456-20466 10.1039/D0NR04995F
- [5] Excited state dynamics of symmetric and asymmetric Cr3(dpa)4Cl2 measured using femtosecond transient absorption spectroscopy? Chao-Han Cheng,Wen-Zhen Wang,Shie-Ming Peng,I-Chia ChenPhys. Chem. Chem. Phys., 2017,19, 25471-25477 10.1039/C7CP03968A
- [6] Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France) Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique DesoeuvreEnviron. Sci.: Processes Impacts, 2013,15, 1536-1544 10.1039/C3EM00215B
- [7] Excimer–monomer switch: a reaction-based approach for selective detection of fluoride? Qiao Song,Angela Bamesberger,Lingyun Yang,Haley Houtwed,Haishi CaoAnalyst, 2014,139, 3588-3592 10.1039/C4AN00522H
- [8] Empowering microfluidics by micro-3D printing and solution-based mineral coating? Hongxia Li,Aikifa Raza,Qiaoyu Ge,Jin-You Lu,TieJun ZhangSoft Matter, 2020,16, 6841-6849 10.1039/D0SM00958J
- [9] Evolution of shape, size, and areal density of a single plane of Si nanocrystals embedded in SiO2 matrix studied by atom probe tomography Bin Han,Yasuo Shimizu,Gabriele Seguini,Celia Castro,Gérard Ben Assayag,Koji Inoue,Yasuyoshi Nagai,Sylvie Schamm-Chardon,Michele PeregoRSC Adv., 2016,6, 3617-3622 10.1039/C5RA26710B
- [10] Excellent electrochemical performance of LiFe0.4Mn0.6PO4 microspheres produced using a double carbon coating process? Yong Ping Huang,Tao Tao,Zheng Chen,Wei Han,Ying Wu,Chunjiang Kuang,Shaoxiong Zhou,Ying ChenJ. Mater. Chem. A, 2014,2, 18831-18837 10.1039/C4TA03994G
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)