The first metal-free procedure for the synthesis of arylsulfonyl fluorides is reported. Under organo-photoredox conditions, aryl diazonium salts react with a readily available SO source (DABSO) to afford the desired product through simple nucleophilic fluorination. The reaction tolerates the presence of both electron-rich and -poor aryls and demonstrated a broad functional group tolerance. To shed the light on the reaction mechanism, several experimental techniques were combined, including fluorescence, NMR, and EPR spectroscopy as well as DFT calculations.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.202101056 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Glyoxylic acid monohydrate promoted reductive addition of sodium sulfinates to pillar[4]arene[1]quinone.
Org Biomol Chem
December 2024
School of Pharmaceutical and Chemical Engineering & Institute for Advanced Studies, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, Zhejiang, China.
An efficient synthesis of sulfonate esters through reductive addition of sodium sulfinates to pillar[4]arene[1]quinone has been established (15 examples). Compared to the arylsulfonylation of -quinone with sodium arylsulfinates under other acidic conditions, this work affords the hydroquinone-type 4--sulfonyl derivatives by using glyoxylic acid monohydrate as a promoter. The protocol features mild reaction conditions and high selectivity and is an alternative protocol for the -sulfonylation of pillar[4]arene[1]hydroquinone.
View Article and Find Full Text PDFEngineered Polymeric Carbon Nitride for Photocatalytic Diverse Functionalization of Electronic-Rich Alkenes.
Angew Chem Int Ed Engl
November 2024
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Republic of Singapore.
Engineered polymeric carbon nitride represents a promising class of metal-free semiconductor photocatalysts for organic synthesis. Herein, we utilized engineered polymeric carbon nitride nanosheets, which exhibit an increased specific surface area and band gap due to enhanced quantum confinement from vacancy enrichment. These nanosheets serve as a heterogeneous organic semiconductor photocatalyst to facilitate diverse functionalizations of electron-rich alkenes, including arylsulfonylation, aminodifluoroalkylation, and oxytrifluoromethylation.
View Article and Find Full Text PDFRongalite induced metal-free C(sp)-H functionalization of indoles: direct access to 3-(sulfonylmethyl) indoles.
Org Biomol Chem
November 2024
Department of Chemistry, National Institute of Technology Warangal, Warangal, Telangana-506004, India.
A rongalite-induced C(sp)-H functionalization reaction has been developed for the synthesis of 3-(phenylsulfonylmethyl) indole derivatives from indole and arylsulfonyl hydrazides. This regioselective C-H functionalization provides a wide range of C-3 sulfonylmethyl indoles with upto 90% yields. Here, rongalite functions as a C1 unit source and a single electron donor.
View Article and Find Full Text PDFPhotolytic -Selective Amino Pyridylation of Aryl Isocyanates with -Amino Pyridinium Ylides for the Synthesis of -Arylsulfonyl Ureas.
J Org Chem
October 2024
Department of Chemistry, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Dadri, Chithera, Gautam Buddha Nagar, UP 201314, India.
Herein, we report an expedient synthesis of aryl sulfonyl ureas and from -amino pyridinium ylides and aryl isocyanates. -Aminopyridinium ylides are synthesized via blue light-emitting diode irradiation of pyridine/isoquinoline and appropriate iminoiodinanes. The strategy involved a hitherto unknown carboamination of imine moieties (of aryl isocyanates) via a three-component reaction of pyridine derivatives/isoquinoline , -aryl sulfonyl iminoiodinanes , and numerous aryl isocyanates at room temperature in 2-methyl tetrahydrofuran to afford the target compounds in moderate to excellent yields.
View Article and Find Full Text PDFMetal-Free Synthesis of Polysubstituted Triazoloquinoxalines Using Alkynols as the Key Building Blocks.
ACS Omega
September 2024
Department of Organic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, 779 00 Olomouc, Czech Republic.
-Phenylenediamines, -nitroanilines, and Boc--phenylenediamines were converted to -Ts/Ns--phenylenediamines, followed by Mitsunobu alkylation with prop-2-yn-1-ols. After one-pot azidation, the resulting intermediates underwent Huisgen cycloaddition, which yielded Ts/Ns-dihydrotriazoloquinoxalines. Cleavage of the arylsulfonyl moiety provided (dihydro)triazoloquinoxalines with the possibility of modifying the position.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!