1,2,6-Thiadiazines treated with visible light and O under ambient conditions are converted into difficult-to-access 1,2,5-thiadiazole 1-oxides (35 examples, yields of 39-100%). Experimental and theoretical studies reveal that 1,2,6-thiadiazines act as triplet photosensitizers that produce O and then undergo a chemoselective [3 + 2] cycloaddition to give an endoperoxide that ring contracts with selective carbon atom excision and complete atom economy. The reaction was optimized under both batch and continuous-flow conditions and is also efficient in green solvents.
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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10521009 | PMC |
http://dx.doi.org/10.1021/acs.orglett.3c02673 | DOI Listing |
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