Silver-catalyzed stereoselective C-4 arylthiodifluoromethylation of coumarin-3-carboxylic acids via a double decarboxylative strategy?
Organic Chemistry Frontiers Pub Date: 2021-12-14 DOI: 10.1039/D1QO01609A
Abstract
A facile silver-catalyzed dual decarboxylation of arylthio-difluoroacetic acid with coumarin-3-carboxylic acids/chromone-3-carboxylic acids was developed. This method provided a unique way to synthesize a series of C-4 arylthiodifluoromethylated 3,4-dihydrcoumarins/C-2 arylthiodifluoro-methylated chromanone derivatives in moderate to good yields under mild conditions. Mechanistic studies confirmed that the methodology proceeds via a bimolecular decarboxylative radical pathway. In addition, experimental studies showed that the C-3 carboxyl group of coumarin-3-carboxylic acids/chromone-3-carboxylic acids and the CF2 group of arylthiodifluoroacetic acids play a crucial role in this transformation.
Recommended Literature
- [1] Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination? Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. SharadaChem. Commun., 2022,58, 1406-1409 10.1039/D1CC06097J
- [2] Excitation energies from ground-state density-functionals by means of generator coordinates A. B. F. da Silva,K. CapellePhys. Chem. Chem. Phys., 2009,11, 4564-4569 10.1039/B902529D
- [3] Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China? Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing LiFood Funct., 2018,9, 4234-4245 10.1039/C8FO00787J
- [4] Dissolution of cork biopolymers in biocompatible ionic liquids Helga Garcia,Rui Ferreira,Marija Petkovic,Jamie L. Ferguson,Maria C. Leit?o,H. Q. Nimal Gunaratne,Luís Paulo N. RebeloGreen Chem., 2010,12, 367-369 10.1039/B922553F
- [5] Emerging investigator series: first-principles and thermodynamics comparison of compositionally-tuned delafossites: cation release from the (001) surface of complex metal oxides? Joseph W. Bennett,Diamond T. Jones,Blake G. Hudson,Joshua Melendez-Rivera,Robert J. Hamers,Sara E. MasonEnviron. Sci.: Nano, 2020,7, 1642-1651 10.1039/C9EN01304K
- [6] Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings Analyst, 1996,121, 785-788 10.1039/AN9962100785
- [7] 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
- [8] Fe/S-Catalyzed synthesis of 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles via redox condensation of o-nitrophenols with acetophenones and methylquinolines? Thi Thu Tram Nguyen,Thanh Binh NguyenOrg. Biomol. Chem., 2021,19, 6015-6020 10.1039/D1OB00976A
- [9] Enabling non-flammable Li-metal batteries via electrolyte functionalization and interface engineering? Jing Yu,Yu-Qi Lyu,Jiapeng Liu,Mohammed B. Effat,Junxiong WuJ. Mater. Chem. A, 2019,7, 17995-18002 10.1039/C9TA03784E
- [10] Excellent energy storage performance in NaNbO3-based relaxor antiferroeic ceramics under a low electric field XuxinCheng,XiaomingChen,PengyuanFan 10.1007/s10832-022-00283-w
Journal Name：Organic Chemistry Frontiers
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.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)