Preparation of Organoboronates through Nickel-Catalyzed Conjunctive Coupling Reactions and Their Applications

Abstract

This thesis will describe the development of two transition metal catalyzed syntheses of organoboronic compounds. The first section describes relevant concepts and precedents for the conjunctive coupling reaction. In the second section of this thesis, nickel catalyzed conjunctive coupling reaction of carboxylic acid derivatives with 9-BBN derived ate complexes will be discussed, where beta-trialkylboryl ketones are obtained as the product. In the third section, the development of alkyl group migration in nickel-catalyzed conjunctive coupling with C(sp3) electrophiles will be discussed. Enantioenriched secondary boronic esters can be prepared from this reaction, and two alkaloid syntheses are disclosed as the application of the method.