In this study, we have successfully applied a visible-light-promoted desulfurization method to the synthesis of deoxysugars, especially 1-deoxyglycose, 2,4-deoxyglycosides, and 2-deoxyglycosides with exclusive α-configuration. Compared to the reported desulfurization under UV light (500 W mercury lamp), this desulfurization under visible light (20 W blue LED) is easy to operate since it does not require a dedicated photochemical reactor, occurs under very mild conditions, and is able to avoid many of the side reactions that often occur during the UV-induced desulfurization.
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http://dx.doi.org/10.1021/acs.joc.3c00046 | DOI Listing |
Nat Commun
October 2024
Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041, China.
C-Glycosides are essential for the study of biological processes and the development of carbohydrate-based drugs. Despite the tremendous hurdles, glycochemists have often fantasized about the efficient, highly stereoselective synthesis of C-glycosides with the shortest steps under mild conditions. Herein, we report a desulfurative radical protocol to synthesize C-alkyl glycosides and coumarin C-glycosides under visible-light induced conditions without the need of an extra photocatalyst, in which stable and readily available glycosyl thiols that could be readily obtained from native sugars are activated in situ by pentafluoropyridine.
View Article and Find Full Text PDFJ Org Chem
January 2024
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China.
A radical 1,2,4-trifunctional reaction of thiosulfonate to unactivated olefin is achieved by a migration strategy under mild conditions. In this reaction, the more unstable primary free radicals are in situ generated after the migration of heteroaryl groups in the presence of DABCO. This trifunctionalization of unactivated olefins involves two C-S bond formations and one C-C bond formation.
View Article and Find Full Text PDFJ Org Chem
July 2023
Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, P. R. China.
RSC Adv
June 2022
Hunan Key Laboratory of Traditional Chinese Veterinary Medicine, Hunan Agricultural University Changsha Hunan 410128 China
A novel method for the metal-free synthesis of amides from thioamides based on visible-light photoredox catalysis and in an air atmosphere is reported. Natural pigment chlorophyll is used as a photosensitizer to generate singlet molecular oxygen O, which is involved in the aerobic desulfurization of thioamides. The protocol provides amides in good yields at room temperature under mild conditions.
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