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Synthesis 2018; 50(12): 2385-2393
DOI: 10.1055/s-0037-1609480
DOI: 10.1055/s-0037-1609480
paper
Synthesis of Isoxazolines and Isoxazoles via Metal-Free Desulfitative Cyclization
We gratefully acknowledge the financial support from the National Science Foundation of China (No. 21072131) and Sichuan University–Lu Zhou Strategic Cooperation Projects (No. 2013 CDLZ-S18).Further Information
Publication History
Received: 03 February 2018
Accepted after revision: 09 March 2018
Publication Date:
14 May 2018 (online)
Abstract
A novel, one-pot reaction for the synthesis of isoxazolines and isoxazoles is developed via a cascade process under metal-free conditions. The approach involves the formation of intramolecular C–N and C–O bonds and intermolecular C–C bonds from aromatic alkenes or alkynes and N-hydroxysulfonamides using hypervalent iodine(VII) and iodine as the oxidant. Activation of C–H and C–C bonds/construction of C–O bonds/elimination of SO2/C–N bond formation is achieved in sequence in the reaction system.
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