Late-Stage Functionalization of 1,2-Dihydro-1,2-Azaborines
Brown, Alec Nathaniel. “Late-Stage Functionalization of 1,2-Dihydro-1,2-Azaborines”. PhD, Boston College, 2015. http://hdl.handle.net/2345/bc-ir:104564.
Described herein are two distinct research projects focused on the development of metal-catalyzed late-stage functionalization strategies for 1,2-dihydro-1,2-azaborines separated into three chapters. The first chapter discusses the development, synthesis, and recent contributions to the field of azaborine chemistry. The second chapter details the development of rhodium catalyzed B-H bond activation for the synthesis of a new class of BN-stilbenes as well as the discovery of a novel B-H to B-Cl transformation that is successful both with B-H azaborines as well as other B-H containing compounds. The third chapter pertains to the development of a B-H and B-Cl tolerant C(3) functionalization strategy through the use of Negishi cross-coupling. Using this methodology, previously unreported isomers of BN-naphthalene and BN-indenyl have been synthesized and characterized.