DOI: 10.1039/C4RA13454K
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Journal Name
RSC Advances
COMMUNICATION
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Based on the above experimental results and the relevant reported
works, 10 a proposed reaction mechanism is outlined in scheme 2.
Firstly, I-/I2 redox cycle promotes TBHP to furnish tert-butoxyl and
tert-butylperoxyl radicals. Sulfinate 1 is oxidized by these oxidative
species into an oxygen-centered radical A that can resonate with the
sulfonyl radical B. Then, amine 2 attacks sulfonyl radical to generate
radical anion C with the loss of a proton. Intermediate C is able to be
oxidized by molecular iodine to produce the final sulfonamide
product 3.
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Scheme 2. Proposed mechanism for TBAI-catalyzed oxidative
coupling of amines with sodium sulfinates
Conclusions
In conclusion, we have developed a practical procedure for the
preparation of sulfonamides through TBAI-catalyzed coupling
of amines with sodium sulfinates under mild conditions. This
methodology tolerates various functional groups including
hydroxyl.
We thank Guangdong Medical College (No. XB1973) for
financial support.
Notes and references
a
School of Pharmacy, Guangdong Medical College, Dongguan 523808,
China.
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/c000000x/
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