RUI: Developing Acetylene-Activated SNAr Reactions

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With an RUI Award from the Chemical Structure, Dynamics and Mechanisms Program, Professor Jeffrey L. Katz of Colby College will research the merging of the synthetically powerful carbon-carbon triple bond, with a classic organic transformation, the nucleophilic aromatic substitution (SNAr) reaction. The Katz group has found ethynyl groups to be sufficient for activating fluorobenzenes toward nucleophilic substitution. Such acetylene-activated SNAr reactions will be pursued in three areas. First, through kinetics measurements and experiments of reaction scope, students in the Katz laboratory will study the electronic nature of acetylene functional groups with respect to aromatic substitution processes. Second, acetylene-activated SNAr chemistry will be exploited for the rapid synthesis of complex heterocycles, and heterocyclic arylethynyl-substituted luminophores. Finally, acetylene-substituted SNAr reactions will be applied to the synthesis of oxacalix[4]arene macrocycles, and the formed oxacalix[4]arenes bearing acetylene groups will be studied as a new class of bifunctional molecular receptors.This RUI award will also support students working with Professor Katz as part of a research-based mentoring program for underrepresented minority students in chemistry at Colby College. Professor Katz is the creator and Director of the Colby Research Scholars (CRS) Program, an academic-year program for minority students to pursue independent research projects with faculty in the sciences as early as their freshman year. Professor Katz also serves as co-Director of the Colby Achievement Program in the Sciences (CAPS), a summer bridge program for entering first-year students from underrepresented backgrounds. In conjunction, these programs seek to recruit and retain minority students into chemistry and other scientific disciplines. Students participating in the CRS and CAPS programs in the Katz laboratory will have active roles in the proposed research, participate in research group meetings, attend and present posters at local and national meetings, and interact academically and socially with other student-scientists.