2-naphthyl pendant aryl groups in quest of copper(I)-arene complexes

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2-naphthyl pendant aryl groups in quest of copper(I)-arene complexes Synthesis of copper(I) complexes with NS2-cyclodecane ligands bearing phenyl and 2-naphthyl pendant aryl groups in quest of copper(I)-arene complexes Chantal Balesdent; Cedric Owens; Michelle Kim; and Rebecca R. Conry* Department of Chemistry, Colby College, Waterville, ME, USA Introduction Copper(I)-arene complexes are relatively rare and therefore their chemistry is not well explored. However, they have been found to be competent aziridination precatalysts.1 We are currently expanding our previous work in which we found Cu-naphthyl binding to a coordinated 1-naphthyl-appended NS2-cyclodecane ligand (1).2, 4 To do so, we are synthesizing analogous ligands with different pendant aryl groups, including the phenyl-appended (phL) and 2-naphthyl-appended (2-napL) NS2-cyclodecane ligands. Synthesis of Ligands The formation of the NS2-cyclodecane macrocyclic ring 2 was accomplished in three steps:3 The first target ligand phL was formed in one step from 2 and 2-bromoethylbenzene: The second target ligand 2-napL was made in three steps from 2 and 2-naphthalenylacetyl chloride, 3. The first step is the formation of 3 (not shown):4 Next, benzene copper triflate will be used as a Cu(I) source to form Cu(I) complexes of these ligands, as shown for phL below:4 Results Ligands phL and 2-napL have been synthesized and characterized. Future Directions The Cu(I) complexes of phL and 2-napL will be fully characterized and any Cu(I)-arene interactions identified via NMR spectroscopy and X-ray crystallography as possible. 1 References 1. Conry, R. R.; Tipton, A. A.; Striejewske, W. S.; Erkizia, E.; Malwitz, M. A.; Caffaratti, A.; Natkin, J. A. Organometallics 2004, 23, 5210 2. Conry, R. R.; Striejewske, W. S. Organometallics 1998, 17, 3146 3. Chandrasekhar, S.; McAuley, A. Inorg. Chem. 1992, 31, 2234 4. unpublished synthesis based on: Conry, R. R.; Striejewske, W. S.; Tipton, A. A. Inorg. Chem. 1999, 38, 2833 Acknowledgements Colby College and ACS-PRF for funding Paul Lee and A. Alex Tipton for previous results