The first examples of rhodium-catalyzed 1,4-conjugate addition reactions of arylboronic acids with ethenesulfonamides

• Published in: Tetrahedron letters Vol. 52; no. 45; pp. 5934 - 5939
• Main Authors: Zilaout, Hicham, van den Hoogenband, Adri, de Vries, Jelle, Lange, Jos H.M., Terpstra, Jan Willem
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 09.11.2011; Elsevier
• Subjects: 14-Conjugate addition; 2-Arylethanesulfonamide; B derivatives; Boronic acid; Catalysis; Catalysts: preparations and properties; Chemistry; Chemistry, Organic; Ethenesulfonamide; Exact sciences and technology; General and physical chemistry; Noncondensed benzenic compounds; Organic chemistry; Organometalloidal and organometallic compounds; Physical Sciences; Preparations and properties; Rhodium; Science & Technology; Tetrahedrons; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; 14-Conjugate addition; Boronic acid; Rhodium; 2-Arylethanesulfonamide; Ethenesulfonamide; ASYMMETRIC 1,4-ADDITION; ARYLATION; SULFONES; ORGANOBORONIC ACIDS; CHLORIDES; ENONES; ARYL; CONJUGATE ADDITION; WATER; Catalytic reaction; Sulfonamide; Transition metal; Amine; Addition reaction; Boron Organic compounds; Platinoid; Boronic acids; Catalyst
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2011.08.108

A one-step procedure is described for the synthesis of 2-arylethanesulfonamides by an unprecedented Rh-catalyzed 1,4-conjugate addition of arylboronic acids with ethenesulfonamides. An unprecedented rhodium-catalyzed 1,4-conjugate addition of arylboronic acids with ethenesulfonamides resulting in the corresponding 2-arylethanesulfonamides is described. The amino substituent, the applied arylboronic acid, the type of Rh-catalyst, and the experimental conditions all affected the reaction outcome.