An efficient metal-free oxidative arylsulfonylation of α,β-unsaturated imides with sulfonylhydrazides leading to isoquinoline-1,3(2H,4H)-dione derivatives has been developed. The procedure involves the generation of sulfonyl radicals via cleavage of the S-N bond of sulfonylhydrazides with sulfonylation and C-H functionalization. The protocol uses the economical and environmentally friendly TBAI-TBHP catalytic system, and the corresponding isoquinoline-1,3(2H,4H)-diones with various functional groups were obtained in moderate to good yields.
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http://dx.doi.org/10.1039/c4ob01651c | DOI Listing |
J Org Chem
August 2022
College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000, P. R. China.
Mild, convenient, and effective TBAI-catalyzed S-H and N-H insertion reactions of α-diazoesters with thiophenols and aromatic amines under metal-free conditions have been described, furnishing a straightforward and general platform for the synthesis of various thioethers and 2-amino-2-oxoacetates in moderate to excellent yields. Moreover, this strategy features simple operation, mild conditions, broad substrate scope, and easy scale-up.
View Article and Find Full Text PDFOrg Biomol Chem
March 2019
College of Science, Hunan Agricultural University, Changsha 410128, People's Republic of China.
A simple, practical and metal-free method has been developed for the synthesis of sulfonamides and β-arylsulfonyl enamines via the selective cleavage of C-N and C-H bonds through the iodine-catalyzed oxidation of arenesulfonyl chlorides and sodium sulfinates with tert-amines. The method uses commercially available inexpensive catalysts and oxidants, and has a wide substrate scope and operational simplicity.
View Article and Find Full Text PDFOrg Biomol Chem
September 2018
School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
A novel TBAI-catalyzed tandem thio-Michael addition/oxidative annulation of allenes and thioamides for the construction of polysubstituted 2-arylthiophenes under a sulfur migration transformation protocol has been developed. The transition-metal-free protocol achieves the oxidative cyclization reaction of thioamides containing electron-rich substituents with allenes to construct polysubstituted thiophenes selectively by controlling oxidation conditions.
View Article and Find Full Text PDFChemistry
September 2016
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.
An aqueous catalytic method for double C-S bond formations that involves alcohol derivatives, organic halides, and sodium thiosulfate has been developed. A diverse range of functionalized sulfides, including pharmaceutical and biological derivatives, can be obtained in an efficient and eco-friendly manner under air. The mechanistic studies revealed that this tetrabutylammonium-iodide-catalyzed/water-assisted reaction generated a mercaptan species as the key intermediate.
View Article and Find Full Text PDFOrg Lett
March 2016
Institute of Organic Chemistry, Westfälische Wilhelms-Universität, Corrensstraße 40, 48149 Münster, Germany.
A transition-metal-free one-pot sequence for the synthesis of 3-peroxy-substituted oxindoles from readily prepared 2-cyano-2-diazo-acetamides is reported. The two-step tandem process includes a highly efficient thermal intramolecular C-H-carbene insertion followed by a tetrabutylammonium iodide (TBAI) catalyzed radical C3-peroxy-functionalization. The protocol provides easy access to a new class of 3-cyano-3-peroxy-disubstituted oxindoles.
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