Abstract The ubiquitous nature of N-heterocycles in bioactive molecules that improve the quality of life and health of humans continues to inspire the development of new technology to simplify access to these scaffolds and provides a fertile ground to enable the training of scientists to achieve their professional aspirations. Our research program has been tailored to provide opportunities for the University of Illinois at Chicago's diverse student body to inspire, teach, and mentor them in their professional development by addressing gaps in organic synthetic repertoire through the development of new selective C–N bond forming reactions by exploiting the reactivity of electrophilic N-aryl nitrogen species generated in situ from aryl azides, nitroarenes, or non-activated anilines. Within GM138388, we have leveraged our understanding these N-aryl nitrogen reactive intermediates to develop new transformations that create C–NHAr bonds. To accomplish this, in Aim 1 we will develop new Fe(II)- catalyzed reductive cascade reactions that construct sp3-C–NHAr bonds intra- or intermolecularly from nitroarenes using silane reductants; in Aim 2 we will develop new single-electron transfer processes that generate N-aryl reactive intermediates with tunable oxygen transfer abilities for the synthesis of N- hydroxyindoles and oxindoles; and in Aim 3, we will develop oxidative methods for accessing electrophilic N-aryl nitrenoids from anilines and apply to the intra- and intermolecular synthesis of N-heterocycles. In this diversity supplement request for Jair N. Powell, we request funds to support his research training and career development. Jair will develop new earth abundant metal-catalyzed reductive methods to transform nitroalkenes into N- heterocycles by harnessing the reactivity of nitrosoalkenes to participate in nitroso-ene or C–N cross coupling reactions. His project will exploit the reactivity trends developed in Specific Aim 1 of GM138388 to construct five- or six-membered N-heterocycles through pericyclic or C–N cross-coupling reactions. By establishing that electrophilic nitrogen catalytic intermediates can be accessed from nitro-groups irrespective of their type, Jair will showcase the generality of our tools to construct novel and bioactive N-heterocycles. To help Jair achieve his goal of obtaining a Ph.D. position in the US pharmaceutical industry, his research training will be guided by maintaining an Individual Development Plan and buttressed with activities designed to sharpen his skills in verbal and written communication, and scientific collaboration, leadership, and teamwork. Jair will be given opportunities to participate in career development workshops and cultivate a diverse professional network to support his ambitions.