Catalytic Group Transfer with Late Metal Nitrenes

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Professor Timothy Warren of Georgetown University is supported by the Inorganic, Bioinorganic and Organometallic Chemistry program to develop catalysts for promoting nitrene insertion into C-H bonds and nitrene addition across olefins. This proposal utilizes bulky beta-diketiminato copper and nickel complexes as catalysts with organoazides as the nitrene source. Current methods limit the nature of the nitrene substituent to strongly electron withdrawing groups, and moving to other nitrene sources will expand the range of applications available to this powerful tool. In addition to insertion of nitrenes into C-H bonds, efforts to add nitrene fragments to olefins, carbon monoxide, and isocyanide are being pursued. Discrete metal-nitrene complexes that can be isolated and characterized play a central role in this chemistry.Both the conversion of hydrocarbons into amines and the conversion of olefins into aziridines are synthetically challenging, high value-added transformations. The broader impacts of this project include exposing students to sophisticated experimental techniques suitable for probing reaction mechanisms in catalytic organometallic transformations.