Synthesis and catalysed hydroboration of styryl sulfonamides

Abstract

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.Key words: boronate esters, catalysed hydroborations, sulfanilamides, vinylaniline.