Part I: Catalytic asymmetric arylation of esters for profen synthesis. Part II: Fast Suzuki coupling of heteroaryl chlorides

Abstract

Transition metal-catalyzed cross-coupling reaction has become a useful methodology for the formation of C-C bond. This thesis describes two new improved methods of the C-C bond formation catalyzed by palladium catalyst. Part one reports a general method of palladium-catalyzed coupling of ester to produce tertiary carbon centers with high yield and exellent ee. It offers a general method for the synthesis of profen drugs. The use of a new biarylphosphine improved stereoselectivity as compared to the previously reported catalyst. Part two describes a new catalytic system for Suzuki-Miyaura coupling of heteroaryl chlorides and heteroayl boronic acids. Most of the major families of heteroaryl chlorides can reached full conversion within minutes to hours at room temperature. The relative reactivity of coupling partners is also studied in this part.