@article{delp_goj_pouy_munro-leighton_lee_gunnoe_cundari_petersen_2011, title={Well-Defined Copper(I) Amido Complex and Aryl Iodides Reacting to Form Aryl Amines}, volume={30}, ISSN={["1520-6041"]}, DOI={10.1021/om101084e}, abstractNote={The CuI complex (IPr)Cu(NHPh) {IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene} reacts with aryl iodides to form diaryl amine products and (IPr)Cu(I), which was confirmed by independent synthesis and characterization. For the reaction with iodobenzene, the products are diphenylamine and aniline. Protection of the hydrogen para to the iodo functionality with ortho-methyl groups results in quantitative conversion to diaryl amine. Combined computational and experimental studies suggest that C−N bond formation most likely occurs via an oxidative addition/reductive elimination sequence.}, number={1}, journal={ORGANOMETALLICS}, author={Delp, Samuel A. and Goj, Laurel A. and Pouy, Mark J. and Munro-Leighton, Colleen and Lee, John P. and Gunnoe, T. Brent and Cundari, Thomas R. and Petersen, Jeffrey L.}, year={2011}, month={Jan}, pages={55–57} } @article{delp_munro-leighton_goj_ramirez_gunnoe_petersen_boyle_2007, title={Addition of s-h bonds across electron-deficient olefins catalyzed by well-defined copper(I) thiolate complexes}, volume={46}, ISSN={["1520-510X"]}, DOI={10.1021/ic070268s}, abstractNote={A series of monomeric (NHC)Cu(SR) (R = Ph or CH2Ph; NHC = N-heterocyclic carbene) complexes have been synthesized and fully characterized including single-crystal X-ray diffraction studies. These complexes catalyze the addition of S-H bonds across electron-deficient olefins to regioselectively produce "anti-Markovnikov" products.}, number={7}, journal={INORGANIC CHEMISTRY}, author={Delp, Samuel A. and Munro-Leighton, Colleen and Goj, Laurel A. and Ramirez, Magaly A. and Gunnoe, T. Brent and Petersen, Jeffrey L. and Boyle, Paul D.}, year={2007}, month={Apr}, pages={2365–2367} } @article{goj_blue_delp_gunnoe_cundari_pierpont_petersen_boyle_2006, title={Chemistry surrounding monomeric copper(I) methyl, phenyl, anilido, ethoxide, and phenoxide complexes supported by N-heterocyclic carbene ligands: Reactivity consistent with both early and late transition metal systems}, volume={45}, DOI={10.1021/ic0611995}, abstractNote={Monomeric copper(I) alkyl complexes that possess the N-heterocyclic carbene (NHC) ligands IPr, SIPr, and IMes [IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, SIPr = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene, IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene] react with amines or alcohols to release alkane and form the corresponding monomeric copper(I) amido, alkoxide, or aryloxide complexes. Thermal decomposition reactions of (NHC)Cu(I) methyl complexes at temperatures between 100 and 130 degrees C produce methane, ethane, and ethylene. The reactions of (NHC)Cu(NHPh) complexes with bromoethane reveal increasing nucleophilic reactivity at the anilido ligand in the order (SIPr)Cu(NHPh) < (IPr)Cu(NHPh) < (IMes)Cu(NHPh) < (dtbpe)Cu(NHPh) [dtbpe = 1,2-bis(di-tert-butylphosphino)ethane]. DFT calculations suggest that the HOMO for the series of Cu anilido complexes is localized primarily on the amido nitrogen with some ppi(anilido)-dpi(Cu) pi-character. [(IPr)Cu(mu-H)]2 and (IPr)Cu(Ph) react with aniline to quantitatively produce (IPr)Cu(NHPh)/dihydrogen and (IPr)Cu(NHPh)/benzene, respectively. Analysis of the DFT calculations reveals that the conversion of [(IPr)Cu(mu-H)]2 and aniline to (IPr)Cu(NHPh) and dihydrogen is favorable with DeltaH approximately -7 kcal/mol and DeltaG approximately -9 kcal/mol.}, number={22}, journal={Inorganic Chemistry}, author={Goj, L. A. and Blue, E. D. and Delp, S. A. and Gunnoe, T. B. and Cundari, T. R. and Pierpont, A. W. and Petersen, J. L. and Boyle, P. D.}, year={2006}, pages={9032–9045} } @article{goj_lail_pittard_riley_gunnoe_petersen_2006, title={Reactions of TpRu(CO)(NCMe)(Ph) with electron-rich olefins: examples of stoichiometric C-S, C-O and C-H bond cleavage}, number={9}, journal={Chemical Communications (Cambridge, England)}, author={Goj, L. A. and Lail, M. and Pittard, K. A. and Riley, K. C. and Gunnoe, T. B. and Petersen, J. L.}, year={2006}, pages={982–984} } @article{goj_blue_delp_gunnoe_cundari_petersen_2006, title={Single-electron oxidation of monomeric copper(I) alkyl complexes: Evidence for reductive elimination through bimolecular formation of Alkanes}, volume={25}, ISSN={["1520-6041"]}, DOI={10.1021/om060409i}, abstractNote={Monomeric Cu(I) alkyl complexes (NHC)Cu(R) (NHC = N-heterocyclic carbene; R = Me or Et) and (dtbpe)Cu(Me) (dtbpe = 1,2-bis(di-tert-butylphosphino)ethane) have been prepared, isolated, and characterized. Single-electron oxidation of the Cu(I) alkyl complexes upon reaction with AgOTf to form putative Cu(II) intermediates of the type [(L)Cu(R)]+ (L = NHC or dtbpe, R = Me or Et) results in the rapid production of (L)Cu(X) (X = OTf) and R2. Experimental studies suggest that the reductive elimination of R2 from Cu(II) occurs through a nonradical bimolecular mechanism. Computational studies of the Cu−Cmethyl yield bond dissociation enthalpies of [(SIPr)Cu−CH3]n+ (80 kcal/mol for n = 0 {Cu(I)} and 38 kcal/mol for n = 1 {Cu(II)}).}, number={17}, journal={ORGANOMETALLICS}, author={Goj, Laurel A. and Blue, Elizabeth D. and Delp, Samuel A. and Gunnoe, T. Brent and Cundari, Thomas R. and Petersen, Jeffrey L.}, year={2006}, month={Aug}, pages={4097–4104} } @article{goj_blue_munro-leighton_gunnoe_petersen_2005, title={Cleavage of X-H bonds (X = N, O, or C) by copper(I) alkyl complexes to form monomeric two-coordinate copper(I) systems}, volume={44}, ISSN={["1520-510X"]}, DOI={10.1021/ic0517624}, abstractNote={The monomeric copper(I) alkyl complexes (IPr)Cu(R) [R = Me or Et; IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene] react with substrates that possess N-H, O-H, and acidic C-H bonds to form monomeric systems of the type (IPr)Cu(X) (X = anilido, phenoxide, ethoxide, phenylacetylide, or N-pyrrolyl) and methane or ethane. Solid-state X-ray crystal structures of the anilido, ethoxide, and phenoxide complexes confirm that they are monomeric systems. Experimental studies on the reaction of (IPr)Cu(Me) and aniline to produce (IPr)Cu(NHPh) suggest that a likely reaction pathway is coordination of aniline to Cu(I) followed by proton transfer to produce methane and the copper(I) anilido complex.}, number={24}, journal={INORGANIC CHEMISTRY}, author={Goj, LA and Blue, ED and Munro-Leighton, C and Gunnoe, TB and Petersen, JL}, year={2005}, month={Nov}, pages={8647–8649} } @article{goj_gunnoe_2005, title={Developments in catalytic aromatic C-H transformations: Promising tools for organic synthesis}, volume={9}, ISSN={["1875-5348"]}, DOI={10.2174/1385272053765051}, abstractNote={Catalytic carbon-carbon bond formation using transition metal complexes typically incorporates the use of an aryl halide or triflate compound (electrophile) in combination with an organometallic reagent (nucleophile). Versatile synthetic methods that allow C-C bond formation of aromatic compounds that proceed through transformation of C-H bonds would be of substantial value. Potential routes for C-C bond formation with aromatic substrates include the hydroarylation of unsaturated compounds (e.g., olefins or alkynes) and oxidative coupling of aromatic compounds and olefins or alkynes. Such reactions can proceed through metal-mediated transformation of C-H bonds. The range of reported catalysts and catalytic cycles for these classes of reactions have been reviewed herein. Keywords: transformations, carbon-hydrogen, carbonylation reactions, oxidative coupling, anti-markovnikov product, toluene, phenylation, palladium-catalyzed oxidative coupling, anilides}, number={7}, journal={CURRENT ORGANIC CHEMISTRY}, author={Goj, LA and Gunnoe, TB}, year={2005}, month={May}, pages={671–685} }