The focus of this research is the development of new methodology for the synthesis of aromatic and heteroaromatic amines from the corresponding aryl and heteroaryl halides, triflates and related compounds using transition metal catalysts. A wide variety of different catalysts types, including both homogeneous and heterogeneous ones, will be studied. While the initial system will utilize stoichiometric aminostannane reagents, a major emphasis will be the development of more environmentally benign reagents, or to utilize only catalytic quantities of the aminostannanes. The application of this approach to several areas of organic synthesis will include: the synthesis of polysubstituted indole derivatives, the use in conjunction with Heck-type arylation processes, and the preparation of enantiomerically pure N-aryl amino acids and other N-aryl amines. Also mechanistic studies will be conducted to investigate the process of reductive-elimination to form aromatic carbon-nitrogen bonds. With this award, the Synthetic Organic Program is supporting the research of Dr. Stephen L. Buchwald of the Department of Chemistry at the Massachusetts Institute of Technology. Professor Buchwald will focus his work on the development of new synthetic methodology for the synthesis of aromatic and heteroaromatic amines using transition metal catalysis. This approach offers an attractive alternative to currently used methods and will be of significant utility both in academic and industrial laboratories where these amines are used as intermediates in the preparation of a vast number of compounds of biological and industrial importance.
