Synthesis and NMR studies with nitrogen-15 labeled ligands used in bifunctional catalysis

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Elijah J. Kragulj, ekragulj@yahoo.com1, Valentín Miranda-Soto, vamiranda77@hotmail.com2, and Douglas Grotjahn, grotjahn@chemistry.sdsu.edu2. (1) Department of Chemistry, San Diego State University, 5500 Campanile Drive, San Diego, CA 92109, (2) Department of Chemistry and Biochemistry, San Diego State University, 5500 Campanile Drive, San Diego, CA 92182
Previous research in the Grotjahn group has shown that pyridyl phosphines dramatically increase the rate of anti-markovnikov alkyne hydration (JACS 2004, 125, 12232, and Chem. Eur. J. 2005, 11, 7147). The increased rate of reaction is thought to be the result of proton transfer or hydrogen bonding involving the heterocyclic ligands. To study these effects in detail, we have developed syntheses of nitrogen-15 labeled pyridine ligands that will allow us to better understand the mechanism of our catalysts through NMR studies of the coupling between the 15N and other nuclei in our test substrate and catalytic intermediate.