Developments and Applications of Methods for Palladium- and Copper-catalyzed Carbon-nitrogen Bond Formation

Download or read book Developments and Applications of Methods for Palladium- and Copper-catalyzed Carbon-nitrogen Bond Formation written by Jeffrey Chih-Yeh Yang and published by . This book was released on 2018 with total page 467 pages. Available in PDF, EPUB and Kindle. Book excerpt: The studies presented in this dissertation are aimed at the development and application of methodologies that enable carbon-nitrogen (C-N) bond formation catalyzed by late transition metals such as palladium and copper. The first part of this thesis focuses on the use of palladium catalysis for the construction of a carbon(sp2)-nitrogen bond in the context of a biphasic continuous-flow system (Chapter 1). The second part of this thesis describes the recent developments of copper-hydride (CuH) catalyzed asymmetric hydroamination for the formation of a-chiral carbon(sp3)-nitrogen bonds from olefins. This work includes the application of CuH catalysis to the synthesis of chiral N-alkyl aziridines (Chapter 2), and the discovery and development of novel electrophilic amines to enable CuH-catalyzed asymmetric hydroamination to directly access primary amines (Chapter 3). Part I. Chapter 1. Use of a "Catalytic" Cosolvent, N,N-Dimethyl Octanamide, Allows the Flow Synthesis of Imatinib with no Solvent Switch A general, efficient method for C-N cross-coupling has been developed using N,N-dimethyloctanamide as a cosolvent for biphasic continuous-flow applications. In addition to utilizing a proper co-solvent, the described method harnesses the superior mixing abilities of a stainless-steel powder packed tube reactor to efficiently couple a wide range of aryl/heteroaryl halides and aryl/heteroaryl/alkyl amines in a short period of time (