Oxidative hydrolysis of aliphatic bromoalkenes: scope study and reactivity insights

Abstract

We have developed an operationally simple method for the synthesis of dialkyl α-bromoketones from bromoalkenes by utilizing a hypervalent iodine-catalyzed oxidative hydrolysis reaction. This catalytic process provides both symmetrical and unsymmetrical dialkyl bromoketones with moderate yields across a broad range of bromoalkene substrates. Our studies also reveal the formation of Ritter-type side products by an alternative reaction pathway.

Keywords

• bromoalkenes
• bromoketones
• hypervalent iodine
• oxidative hydrolysis
• ritter-type