Development of New Metal_Catalyzed Hydroacylation and Hydroarylation Processes

Massachusetts Institute Of Technology, Cambridge MA

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Abstract

DESCRIPTION (provided by applicant): This proposal focuses on new metal-catalyzed hydroacylation and hydroarylation reactions to form biologically active molecules, such as chiral amines, differentially substituted hydrazines, isoindolones, and indazolones. Previously reported metal-catalyzed hydroacylation processes generally involve the addition of an acyl and hydride group across the face of all carbon ¿-systems. There has been limited work of hydroacylation reactions where the ¿-acceptor contains a heteroatom. The emphasis of this proposal is the investigation of the metal-catalyzed hydroacylation and hydroarylation of ¿-systems that contain one more heteroatoms (ketimines and diazenes). Following the successful achievement of these reactions we will explore a C-H activation strategy to convert the generated chiral amines and hydrazides to the corresponding cyclic isoindolones, and indazolones, respectively. In addition to exploring the hydroacylation of ketimines, we will examine the decarbonylation pathway to achieve the hydroarylation of ketimines. Successful establishment of these methodologies would find wide application in the fields of medicinal chemistry, drug discovery, and pharmaceutical research by allowing for the direct rapid assembly of important nitrogen containing biologically active molecules.