We have prepared the aryl sulfonamides 4,4′ -R-C 6 H 4 SO 2 NHC 6 H 4 CH=CH 2 (R = CH 3 , 1a; NO 2 , 1b) by addition of 2 equiv. of 4-vinylaniline to the corresponding sulfonyl chlorides. The disulfonamides 4,4,4′ -(R-C 6 H 4 SO 2 ) 2 -NC 6 H 4 CH=CH 2 (R = CH 3 , 2a; NO 2 , 2b) were also prepared using 4-vinylaniline and 2 equiv. of the sulfonyl chlorides in the presence of DMAP. Although hydroborations of sulfanilamide derivatives 1 suffered from competing hydrogenation reactions, judicious choice of the transition metal catalyst gave selective formation of either the primary or secondary boronate esters in hydroborations of 2a.Résumé : On a préparé les aryl sulfonamides, 4,4′ -R-C 6 H 4 SO 2 NHC 6 H 4 CH=CH 2 (R = CH 3 , 1a; NO 2 , 1b) par l'addition de deux équivalents de 4-vinylaniline aux chlorures de sulfonyle correspondants. On a aussi préparé les disulfonamides 4,4,4′ -(R-C 6 H 4 SO 2 ) 2 NC 6 H 4 CH=CH 2 (R = CH 3 , 2a; NO 2 , 2b) à partir de la 4-vinylaniline et de deux équivalents de chlorures de sulfonyle, en présence de DMAP. Quoique les réactions d'hydroboration des dérivés sulfanilamides 1 soient en compétition avec les réactions d'hydrogénation, un choix judicieux d'un catalyseur à base d'un métal de transition permet d'obtenir la formation sélective des boronates soit primaires ou secondaires lors des hydroborations du composé 2a.Mots clés : esters de l'acide boronique, hydroborations catalysées, sulfanilamides, vinylaniline.[Traduit par la Rédaction] Wynberg et al.
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