Chemoselective and Regioselective Oxidative

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Chemoselective and Regioselective Oxidative Couplings of Aromatic Heterocycles Brenton DeBoef, Department of Chemistry, University of Rhode Island, Kingston, RI 02881 Summary Classification of Non-Directed Oxidative Coupling Reactions Class I (low pH) Class III (buffered) Class IV (high pH) Oxidative coupling is a powerful method by which two unfunctionalized substrates can be directly coupled to form a new C-C bond. We have hypothesized that the variety of reaction conditions that exist for the oxidative formation of biaryl C-C bonds from unfunctionalized arenes may be classified according to their relative pH. A systematic study involving benzofuran substrates has validated this hypothesis. The resulting rubric can be applied to predict the best conditions for the oxidative coupling of a given substrate. The data suggests that high pH reactions proceed via a proton abstraction mechanism, while those at low pH proceed via electrophilic palladation. Class I II III IV Oxidant H4PMo11VO40 + O2 K2CO3 + air AgOAc or Cu(OAc)2 Solvent AcOH or PivOH PivOH Dioxane % Yield (2 : 3) 81% (>99:1) n/a 74% (1:1) 84% (1:6) Reaction Time 25 min. 3 hrs. 12 hrs. Oxidative Coupling as an Efficient Method for Synthesizing Biaryls Class I : DeBoef, et.al. Org. Lett., 2007, 9, 3137–3139. Class II: Fagnou et al. J. Org. Chem., 2008, 73 , 5022–5028. (Incompatible with intermolecular reaction) Class III: DeBoef, et.al. Org. Lett., 2007, 9, 3137–3139. Fagnou et al. Science 2007, 316, 1172-1175. Fagnou et al. J. Am. Chem. Soc. 2007, 129, 12072–12073. Class IV: DeBoef, et al. Tetrahedron Lett., 2008, 49, 4050-4053. Mechanistic Insight Need for Milder Conditions Acknowledgements This work was supported by the National Science Foundation (CAREER 0847222), the Petroleum Research Fund (47019-G1) and a Pilot/Feasibility Grant from the Rhode Island INBRE Program (NIH-NCRR P20RR016457).