Ketones, as essential functional group skeletons, have garnered significant interest due to their diverse transformations. Herein, we describe a versatile photoredox catalyzed deacylation-aroylation strategy that enables the direct transformation of alkyl ketones to aryl ketones. This process involves photoredox deacylation of dihydroquinazolinones derived from alkyl ketones to generate alkyl radicals, followed by subsequent NHC-catalyzed or NHC-mediated radical aroylation.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.orglett.4c02576 | DOI Listing |
PLoS One
January 2025
Department of Molecular Microbiology and Immunology, University of Missouri, Columbia, Missouri, United States of America.
Human neutrophils are abundant, short-lived leukocytes that turn over at a rate of approximately 1011 cells/day via a constitutive apoptosis program. Certain growth factors, inflammatory mediators and infectious agents can delay apoptosis or induce neutrophils to die by other mechanisms. Nonetheless, a large body of data demonstrates that apoptosis of untreated neutrophils typically ensues within 24 hours of cell isolation and in vitro culture.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry and Biochemistry, University of California-Los Angeles, Los Angeles, California 90095-1569, United States.
The homolytic cleavage of C-C bonds adjacent to specific functional groups has lately emerged as a versatile approach for molecular diversification. Despite the ubiquity and synthetic utility of ketones, radical fragmentation of their α-C-C bonds has proven to be a formidable challenge. Here, we present a broadly applicable deacylative strategy designed to homolytically cleave aliphatic ketones of various complexities, including transformations of cycloalkanones into carboxylic acids tethered to C-centered free radicals that can be engaged in diverse radical-based processes.
View Article and Find Full Text PDFMolecules
December 2024
Department of Chemistry & Biochemistry, California State University, Fresno, CA 93740, USA.
Prostate cancer remains a significant global health concern, prompting ongoing exploration of novel therapeutic agents. Licochalcone A, a natural product in the chalcone family isolated from licorice root, is characterized by its enone structure and demonstrates antiproliferative activity in the micromolar range across various cell lines, including prostate cancer. Building on our prior success in enhancing curcumin's antiproliferative potency by replacing the substituted phenol with a 1-alkyl-1H-imizadol-2-yl moiety, we applied a similar approach to design a new class of licochalcone A-inspired chalcones.
View Article and Find Full Text PDFOrg Lett
December 2024
Center for Metareceptome Research, Graduate School of Pharmaceutical Sciences, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea.
Aerobic nitro-nitrite isomerization of secondary nitroalkanes is postulated to proceed via the intermediacy of the α-nitro alkyl radical, where the corresponding Nef-type products, ketones, and nitrogen monoxide can be obtained as byproducts. To explore the catalytic aerobic carbooximation of alkenes using secondary nitroalkanes, phase-transfer catalysis of KSeCN and TBAI has been developed. The current aerobic carbooximation of alkenes utilizes nitroalkanes as both radical and nitrogen monoxide sources in water without external oxidants and prefunctionalized nitroalkanes.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry, University of Washington, Seattle, Washington 98195, United States.
Hydroalkylation of terminal alkynes is a powerful approach to the synthesis of disubstituted alkenes. However, its application is largely unexplored in the synthesis of α,β-unsaturated carbonyls, which are common among synthetic intermediates and biologically active molecules. The thermodynamically less stable -isomers of activated alkenes have been particularly challenging to access because of their propensity for isomerization and the paucity of reliable -selective hydroalkylation methods.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!