Transfer Hydrogenative Hydroaminoalkylation and Imine Addition

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In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Michael J. Krische of the Department of Chemistry and Biochemistry at the University of Texas at Austin will explore new strategies for the formation of C-C bonds via hydroaminoalkylation. In such processes, hydrogen exchange between amines and pi-unsaturated reactants generates transient imine-organometal pairs that combine to form products of imine addition in the absence of stoichiometric byproducts. Unlike classical imine additions, direct amine-unsaturated C-C couplings (a) bypass discrete preparation of stoichiometric main-group organometallics and, consequently, circumvent generation of molar quantities of metallic waste, and (b) avoid discrete imine formation to enhance step-economy. These studies could offer more efficient, byproduct-free routes to important commodity chemicals (plastics, foams, pharmaceutical and agrochemicals) through the direct C-C coupling of basic chemical feedstocks. Byproduct-free catalytic methods for chemical manufacturing eliminate chemical waste at the source and, hence, are environmentally benign. In addition, this project will provide excellent training of students, from pre-undergraduate to post-doctoral, including those from groups historically underrepresented in the sciences.