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JOURNAL ARTICLE
RESEARCH SUPPORT, NON-U.S. GOV'T
Regiocontrolled Synthesis of α-Sulfonylmethyl o-Nitrostyrenes via ZnI 2 -Mediated Sulfonylation and AgNO 2 /Pd(PPh 3 ) 4 -Promoted o-Nitration.
Journal of Organic Chemistry 2017 October 7
We report herein the AgNO2 /Pd(PPh3 )4 -promoted regiocontrolled o-nitration of α-sulfonylmethylstyrenes in MeNO2 with good yields. The o-nitration process provides a series of sulfonyl o-nitrostyrenes. Substituted α-sulfonylmethylstyrenes were synthesized from ZnI2 -mediated sulfonylation of substituted α-methylstyrenes and sodium sulfinates (RSO2 Na) in MeCN with good to excellent yields. The structures of the key products were confirmed by X-ray crystallography. A plausible mechanism has been proposed herein.
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