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Hypervalent Iodine Mediated Sulfonamide Synthesis
Author(s) -
Poeira Diogo L.,
Macara João,
Faustino Hélio,
Coelho Jaime A. S.,
Gois Pedro M. P.,
Marques M. Manuel B.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900259
Subject(s) - hypervalent molecule , umpolung , chemistry , iodine , reagent , sulfonamide , sulfonyl , reactivity (psychology) , yield (engineering) , combinatorial chemistry , organic chemistry , functional group , catalysis , alkyl , nucleophile , medicine , alternative medicine , materials science , polymer , pathology , metallurgy
A new metal‐free sulfonylation reaction is described. The method takes advantage of the Umpolung reactivity and group‐transfer properties of iodine(III) compounds, combining hypervalent iodine reagents and sulfinate salts to deliver a clean and mild transfer of sulfonyl groups to amines and anilines. A total of 25 sulfonamides was synthesised in up to 99 % yield, even on gram‐scale. The reaction mechanism was investigated by ESI‐MS and DFT calculations.