Journal
ORGANIC LETTERS
Volume 19, Issue 17, Pages 4472-4475Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02010
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Funding
- National Natural Science Foundation of China [21672037, 21532001]
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N-Radical initiated aminosulfonylation of unactivated C(sp(3))-H bond through insertion of sulfur dioxide in the presence of visible light is reported. O-Aryl oximes react with DABCO center dot(SO2)(2) smoothly at room temperature under blue LED irradiation without any metals or photoredox catalysts, generating diverse 5,6-dihydro-4H-1,2-thiazine 1,1-dioxides in good yield. Additionally, this approach can be extended to the synthesis of 1H-benzo[d][1,2]thiazine 2,2-dioxides. During the reaction process, an N-radical is initiated by the treatment of O-aryl oximes with DABC center dot(SO2)(2) under visible-light irradiation. It is followed by aminosulfonylation of a nearby C(sp(3)) H bond through 1,5-hydrogen atom transfer with accompanying insertion of sulfur dioxide to provide 1,2-thiazine 1,1-dioxide derivatives.
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