Radical Functionalization of B-Alkylcatecholboranes

Significance

Herein, a very elegant and useful method for the functionalization of alkenes by means of the radical reaction of the derived B-alkyl­catecholboranes with vinyl sulfones is described. Phenyl sulfones of various kinds, bearing a conjugated multiple bond, including tosyl cyanide, can be involved in this reaction. Although the method was demonstrated on unfunctionalized polycyclic alkenes, the mild conditions of the reaction offer good functional-group compatibility. The synthetic usefulness of this approach was demonstrated on a number of very interesting transformations of some alkenes.