Date of Award
LuAnne M. McNulty
Cis-Alkenes provide the basic structure and reactivity for a variety of compounds, from the common chemicals found in any organic laboratory to advanced drugs used to treat cancer or suppress the immune system (Littke & Fu, 2002). Synthetically, alkenes are also of use in that they serve as a site for further chemistry. Historically, Z-alkenes have been more difficult to synthesize than their E-counterparts (McNulty et al., 2010; Siau, Zhang, & Zhao, 2012). Furthermore, in many reactions, a mixture of E- and Z- conformations of the alkene is produced. Such differences may seem trivial upon first inspection, but because there can be no rotation around the alkene bond, a change in conformation can drastically change the functionality of the molecule. There have been many efforts to force the synthesis of the Z-alkene, revealing that various coupling reactions are adept at forcing a desired conformation (Siau et al., 2012). The Suzuki-Miyaura coupling is one such reaction. The Suzuki-Miyaura coupling is also desirable for the non-toxicity of the reaction conditions and ease of synthesizing the starting materials (Siau et al., 2012). To date, the efficacy of Suzuki-Miyaura couplings with alkyl halides has been demonstrated with reported good yields (Littke, Dai, & Fu, 2000; Siau et aI., 2012). The feasibility of forcing the z-conformation by using a cyclic alkene as the substrate for the reaction was investigated. To test this possibility, a cyclic boronic half-acid (CBHA) was reacted with various alkyl halides under differing conditions. HNMR was used for analysis. The reaction, though offering only the Z-conformation of the desired product, produced a mixture of other products. Finally, the mechanism of the reaction was explored.
French, Daniel Lee, "Suzuki-Miyaura Reactions Are Used to Synthesize Z-Alkenes from Cyclic Boronic Half-Acids" (2014). Undergraduate Honors Thesis Collection. 205.