| Popis: |
A practical oxidative Heck reaction between organoboronic acids and ethenesulfonyl fluoride (ESF) is developed. Aryl- and heteroaryl-boronic acids react efficiently and stereoselectively with ESF in the presence of a catalytic amount of Pd(OAc)2 and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) or AgNO3 in AcOH to afford the corresponding E-isomer β-arylethenesulfonyl fluoride products. The utility of this reaction is exemplified by an expanded scope of 47 examples including N-, O-, and S-containing heteroaromatics, demonstrated chemoselectivity over aryliodides, and gram-scale operation without the requirement for strict anhydrous or oxygen-free conditions. Furthermore, this procedure discriminates against the formation of arylboronic acid homo-coupling byproducts. In addition, the preparation the first aryl vinylsulfonate polymer, a material with functionalizable Michael acceptor sites, from a starting arylboronic acid is described. |
