A novel multicomponent sulfonylation of alkenes is described for the assembly of various β-substituted arylsulfones using cheap and easily available KSO as a sulfur dioxide source. Of note, the procedure does not need any extra oxidants and metal catalysts and exhibits a relatively wide substrate scope and good functional group compatibility. Mechanistically, an initial arylsulfonyl radical is formed involving the insertion of sulfur dioxide with aryl diazonium salt, followed by alkoxyarylsulfonylation or hydroxysulfonylation of alkenes.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.joc.2c03036 | DOI Listing |
Chem Asian J
January 2025
Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Gui-zhou Province, Green Pharmaceuticals Engineering Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, 563006, P. R. China.
N-acyl/sulfonyl-α-phosphonated 1,2,3,4-tetrahydroiso-quinolines (THIQs) are significant structural motifs in organic synthesis and drug discovery. However, the one-pot approach enabling direct difunctionalization of THIQs remains challenging. Herein we report a photomediated one-pot multicomponent cascade reaction to access N-acyl/sulfonyl-α-phosphonated THIQs via twice acyl/sulfonyl iminium.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Chemistry, Indian Institute of Science Education and Research (IISER) Tirupati, Tirupati 517619, India.
Diastereoselective synthesis of -3,4-difunctionalized tetrahydroquinoline and chromane derivatives via the oxo-sulfonylation of 1,7-enynes is demonstrated. The reaction involves a three-component oxidative radical polar crossover (ORPC) approach wherein a vinyl carbocation intermediate undergoes nucleophilic substitution to afford the corresponding keto functional group. Deprotection of the N-Ts group, gram-scale synthesis, and other synthetic applications were illustrated.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
School of Chemical Engineering, Dalian University of Technology, Dalian, 116024, China.
In this work, a multicomponent polymerization (MCP) approach involving bipyrroles, sulfonyl azides, and diynes was developed to afford a library of poly(bipyrrole-sulfonylimide)s (PPSIs) in high yields and molecular weights, which were further modified to form unique sulfur dioxide (SO) generators. Bipyrroles served as carbon-based nucleophiles to undergo Cu-catalyzed C-C coupling during the MCP. Upon post-MCP modification by transforming the bipyrrole unit to boron dipyrromethene (BODIPY) and the sulfonylimide moiety to sulfonamide, poly(BODIPY-sulfonamide)s (PBSAs) were obtained as potent anticancer therapeutic agents.
View Article and Find Full Text PDFOrg Lett
November 2024
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, P. R. China.
A generality-oriented and adaptive α-sulfonylation of alkynes via photoinduced multicomponent radical cross-coupling of terminal alkynes with sulfinates and a variety of alcohols, thiophenols, or selenophenols has been explored. This protocol features mild conditions, good functional group tolerability, broad substrate scope, excellent chemo-, site-, and stereoselectivity, and applicability to late-stage functionalization. It provides a modular platform for the synthesis of value-added structurally diverse α-sulfonyl-containing multisubstituted alkenes from simple precursors.
View Article and Find Full Text PDFOrg Lett
August 2024
Department of Chemistry, Rice University, Houston, Texas 77005, United States.
We report a minimalist gaseous sulfonyl-chloride-derived reagent for multicomponent bioconjugation with amine, phenol, or aniline reagents to afford urea or carbamate products. With the utilization of a gas-phase reagent for a reaction mediated by metal ions, a variety of biologically relevant molecules, such as saccharide, poly(ethylene glycol), fluorophore, and affinity tag, can be efficiently cross-linked to the N terminus or lysine side-chain amines on natural polypeptides or proteins.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!