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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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
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cited_by cdi_FETCH-LOGICAL-a390t-e4e99eb52892b1c111b333936fbe4b6221b9711f96f4ad52609cd0dfbcc63f073
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container_end_page 8913
container_issue 48
container_start_page 8907
container_title Organic letters
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creator Bao, Zhaowei
Zou, Juan
Mou, Chengli
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description 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.
doi_str_mv 10.1021/acs.orglett.2c03770
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title Direct Reaction of Nitroarenes and Thiols via Photodriven Oxygen Atom Transfer for Access to Sulfonamides
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