Copper-Catalyzed Reactions of Organoboron Compounds

Abstract

The discovery, development, scope, and mechanistic studies of three new copper-catalyzed transformations of organoboron compounds are described herein. Specifically, Chapter 1 details the development and scope of the first general method for SN2'-selective substitution of primary allylic chlorides using aryl boronic esters as nucleophiles. The formal anti-Markovnikov hydroamination of 9-alkyl-9-BBN derivatives, which are conveniently prepared from the hydroboration of terminal alkenes, to give tertiary alkyl amines is discussed in Chapter 2. Chapter 3 describes the development, scope, and mechanistic studies of the copper-catalyzed electrophilic amination of aryl boronic esters and its application to the synthesis of hindered N,N-dialkyl anilines.