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Harnessing the TEMPO-Catalyzed Aerobic Oxidation for Machetti-De Sarlo Reaction toward Sustainable Synthesis of Isoxazole Libraries

Murugan Vadivelu, Sugirdha Sampath, Kesavan Muthu, Kesavan Karthikeyan* and Chandrasekar Praveen*

*Crescent Institute of Science and Technology, Vandalur, Chennai 600048, Tamil Nadu; CSIR, Alagappapuram, Karaikudi 630003, Tamil Nadu, India, Email: karthiclrigmail.com; chandrasekar.praveengmail.com

M. Vadivelu, S. Sampath, K. Muthu, K. Karthikeyan, C. Praveen, J. Org. Chem., 2019, 84, 13636-13645.

DOI: 10.1021/acs.joc.9b01896 (free Supporting Information)



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Abstract

The use of 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) as catalyst enables a Machetti-De Sarlo reaction of nitroalkenes with alkynes/alkenes under sustainable conditions to afford a library of isoxazole/isoxaline products.


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proposed mechanism



Key Words

isoxazoles, TEMPO, oxygen, organocatalysis, green chemistry


ID: J42-Y2019