Direct Reaction of Nitroarenes and Thiols via Photodriven Oxygen Atom Transfer for Access to Sulfonamides

Sulfonamide is a common motif in medicines and agrochemicals. Typically, this class of functional groups is prepared by reacting amines with sulfonyl chlorides that are presynthesized from nitro compounds and thiols, respectively. Here, we report a novel strategy that directly couples nitro compound...

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Bibliographic Details
Published in:Organic letters 2022-12, Vol.24 (48), p.8907-8913
Main Authors: Bao, Zhaowei, Zou, Juan, Mou, Chengli, Jin, Zhichao, Ren, Shi-Chao, Chi, Yonggui Robin
Format: Article
Language:English
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Summary:Sulfonamide is a common motif in medicines and agrochemicals. Typically, this class of functional groups is prepared by reacting amines with sulfonyl chlorides that are presynthesized from nitro compounds and thiols, respectively. Here, we report a novel strategy that directly couples nitro compounds and thiols to form sulfonamides atom- and redox-economically. Mechanistic studies suggest our reaction proceeds via direct photoexcitation of nitroarenes that eventually transfers the oxygen atoms from the nitro group to the thiol unit.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03770