A facile and highly efficient visible-light photoredox-catalyzed protocol for aryldifluoromethylation of acrylamides was developed using -(difluoromethyl)sulfonium salt as the difluoromethyl source. With this method, pharmaceutically interesting CFH-containing oxindoles were readily accessed from -arylacrylamides, and this method featured mild reaction conditions, a broad scope of substrates, good tolerance of functional groups, and good to excellent yields. Control experiments revealed that this protocol proceeded through a difluoromethylation/cyclization cascade process.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/d3ob00488k | DOI Listing |
Org Lett
January 2025
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
4'-Selective alkylation of nucleosides has been recognized as one of the ideal and straightforward approaches to chemically modified nucleosides, but such a transformation has been scarce and less explored. In this Letter, we combine a visible-light-mediated photoredox catalysis and hydrogen atom transfer (HAT) auxiliary to achieve β-C(sp)-H alkylation of alcohol on tetrahydrofurfuryl alcohol scaffolds and exploit it for 4'-selective alkylation of nucleosides. The reaction involves an intramolecular 1,5-HAT process and stereocontrolled Giese addition of the resultant radicals.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
University of Science and Technology of China, Department of Polymer Science and Engineering, 96 Jinzhai Road, 230026, , 230026, Hefei, CHINA.
Understanding the interplay between gasotransmitters is essential for unlocking their therapeutic potential. However, achieving spatiotemporally controlled co-delivery to target cells remains a significant challenge. Herein, we propose an innovative strategy for the intracellular co-delivery of carbon monoxide (CO) and nitric oxide (NO) gasotransmitters under clinically relevant wavelengths.
View Article and Find Full Text PDFOrg Lett
January 2025
Organic Chemistry Department, Faculty of Science, Autonomous University of Madrid, 28049 Madrid, Spain.
The functionalization of the C-N bond of amines is a straightforward strategy for the construction of complex scaffolds or for the late-stage functionalization of pharmaceuticals. Herein, we describe a photoredox-catalyzed strategy for the deaminative alkylation of primary amine-derived isonitriles that provides unnatural amino acid derivatives under mild conditions. The use of silacarboxylic acids as silyl radical precursors enables the generation of carbon-centered radicals that allow the construction of Csp-Csp bonds via a Giese-type addition, avoiding the undesired hydrodeamination product.
View Article and Find Full Text PDFChemistry
January 2025
Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, 400715, Chongqing, China.
A visible-light-mediated strategy is reported for the direct synthesis of polychlorinated vicinal diaryl alkanes from aryl alkenes and chloroform. In this approach, two haloalkyl radicals generated from chloroform via halogen atom transfer (XAT) and direct single electron transfer (SET) within the same photoredox catalysis cycle enable the 1,4-dichloromethyldimerization of alkenes. Besides chloroform, this strategy is applicable to carbon tetrachloride, bromotrichloromethane, and α-bromo carboxylic esters, yielding corresponding 1,4-disubstituted vicinal diaryl alkanes.
View Article and Find Full Text PDFOrg Lett
January 2025
College of New Energy, State Key Laboratory of Heavy Oil Processing, China University of Petroleum (East China), 266580 Qingdao, P. R. China.
To provide fluorinated allylamines, a visible-light photocatalytic C-F/C-H coupling of easily accessible -difluoroalkenes and secondary -alkylanilines was described. The protocol proceeded under mild conditions, with excellent functional group compatibility and a broad scope including complex natural product derivatives, thus providing a green method for the preparation of high-value functionalized monofluoroalkenes. Mechanistic studies elucidated a photoredox catalyzed radical-radical coupling pathway.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!