2. C-X Bond Forming Cross-Couplings
2b. Mechanism
Giri, R.: Hartwig, J.F. “Cu(I) Amido Complexes in the Ullmann Reaction. Reactions of Cu(I)-Amido Complexes with Iodoarenes with and without Autocatalysis by CuI” J. Am. Chem. Soc. 2010 132, 15860-15863. [doi]
Klinkenberg, J.L.; Hartwig, J.F. “Slow Reductive Elimination from Arylpalladium Parent Amido Complexes” J. Am. Chem. Soc. 2010 132, 11830-11833. [doi]
Tye, J.W.; Weng, Z.; Giri, R.; Hartwig J.F. “Copper(I) Phenoxide Complexes in the Etherification of Aryl Halides” Angew. Chem. Int. Ed. 2010, 49, 2185-2189. [html]
Alvaro, E.; Hartwig, J. F. Resting State and Elementary Steps of the Coupling of Aryl Halides with Thiols Catalyzed by Alkylbisphosphine Complexes of Palladium. J. Am. Chem. Soc. 2009, 131, 7858-7868. [doi]
Barrios-Landeros, F.; Carrow, B. P.; Hartwig, J. F.Effect of Ligand Steric Properties and Halide Identity on the Mechanism for Oxidative Addition of Haloarenes to Trialkylphosphine Pd(0) Complexes. J. Am. Chem. Soc. 2009, 131, 8141-8154. [doi]
Hartwig, J.F. Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides Acc. Chem. Res.2008, 41, 1534-1544. [doi]
Shen, Q. and J. F. Hartwig [(CyPF-tBu)PdCl2]: An Air-Stable, One-Component, Highly Efficient Catalyst for Amination of Heteroaryl and Aryl Halides. Org. Lett. 2008, 18, 4109-4112. [doi]
Tye, J. W., Weng, Z., Johns, A. M., Incarvito, C. D., and J. F. Hartwig Copper Complexes of Anionic Nitrogen Ligands in the Amidation and Imidation of Aryl Halides. J. Am. Chem. Soc. 2008 130 (330) p. 9971-9983. [doi]
Stambuli, J.P., Weng, Z., Incarvito, C.D., and J. F. Hartwig, Reductive Elimination of Ether from T-Shaped, Monomeric Arylpalladium Alkoxides. Angew. Chem., Int. Ed. 2007 4 6(40) p. 7674-7677. [doi]
Barrios-Landeros, F., Carrow, B.P., and J. F. Hartwig, Autocatalytic Oxidative Addition of PhBr to Pd(PtBu3)2 via Pd(PtBu3)2(H)(Br). J. Am. Chem. Soc. 2008 130 (18) p. 5842-5843. [doi]
Shekhar, S., and J. F. Hartwig, Effects of Bases and Halides on the Amination of Chloroarenes Catalyzed by Pd[P(tBu3)]2. Organometallics, 2007. 26 (2): p. 340-351.
[doi]Fujita, K.I., Yamashita, M, Puschmann, F., Alvarez-Falcon, M.M., Incarvito, C.D., and J. F. Hartwig, Organometallic Chemistry from Amidate Complexes. Reductive elimination of N-Aryl Amidates from Palladium(II). J. Am. Chem. Soc., 2006. 128 (28): p.9044-9045.
[doi]Shekhar, S., Ryberg, P., Hartwig, J. F., Mathew, J. S., Blackmond, D. G., Strieter, E. R., and S. L. Buchwald, Reevaluation of the Mechanism of the Amination of Aryl Halides Catalyzed by BINAP-Ligated Palladium Complexes. J. Am. Chem. Soc., 2006. 128 (11): p. 3584-3591.
[doi]Shekhar, S., Ryberg, P., and J. F. Hartwig, Oxidative Addition of Phenyl Bromide to Pd(BINAP) vs Pd(BINAP)(amine). Evidence for Addition to Pd(BINAP). Org. Lett., 2006. 8 (5): p. 851-854.
[doi]Mann, G., Shelby, Q., Roy, A. H., and J. F. Hartwig, Electronic and Steric Effects on the Reductive Elimination of Diaryl Ethers from Palladium(II). Organometallics, 2003. 22 (13): p. 2775-2789.
[doi]Roy, A. H. and J. F. Hartwig, Directly Observed Reductive Elimination of Aryl Halides from Monomeric Arylpalladium(II) Halide Complexes. Journal of the American Chemical Society, 2003. 125(46): p. 13944-13945.
[doi]Yamashita, M., Cuevas Vicario, J. V., and J. F. Hartwig, Trans Influence on the Rate of Reductive Elimination. Reductive Elimination of Amines from Isomeric Arylpalladium Amides with Unsymmetrical Coordination Spheres. Journal of the American Chemical Society, 2003. 125 (52): p. 16347-16360.
[doi]Alcazar-Roman, L. M. and J. F. Hartwig, Mechanistic studies on oxidative addition of aryl halides and triflates to Pd(BINAP)2 and structural characterization of the product from aryl triflate addition in the presence of amine. Organometallics, 2002. 21 (3): p. 491-502.
[doi]Stambuli, J. P., Buhl, M., and J. F. Hartwig, Synthesis, characterization, and reactivity of monomeric, arylpalladium halide complexes with a hindered phosphine as the only dative ligand. Journal of the American Chemical Society, 2002. 124 (32): p. 9346-9347.
[doi]Alcazar-Roman, L. M. and J. F. Hartwig, Mechanism of aryl chloride amination: Base-induced oxidative addition. Journal of the American Chemical Society, 2001. 123 (51): p. 12905-12906.
[doi]Roy, A. H. and J. F. Hartwig, Reductive elimination of aryl halides from palladium(II). Journal of the American Chemical Society, 2001. 123 (6): p. 1232-1233.
[doi]Alcazar-Roman, L. M., Hartwig, J. F., Rheingold, A. L., Liable-Sands, L. M., and I. A. Guzei, Mechanistic studies of the palladium-catalyzed amination of aryl halides and the oxidative addition of aryl bromides to Pd(BINAP)2 and Pd(DPPF)2: An unusual case of zero-order kinetic behavior and product inhibition. Journal of the American Chemical Society, 2000 122 (19): p. 4618-4630.
[doi]Hamann, B. C. and J. F. Hartwig, Systematic variation of bidentate ligands used in aryl halide amination. Unexpected effects of steric, electronic, and geometric perturbations. Journal of the American Chemical Society, 1998 120 (15): p. 3694-3703.
[doi]Hartwig, J. F., Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides. Accounts of Chemical Research, 1998 31 (12): p. 852-860.
[doi]Hartwig, J. F., Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: Scope and mechanism. Angewandte Chemie-International Edition, 1998. 37 (15): p. 2047-2067.
[abstract][pdf]Mann, G., Baranano, D., Hartwig, J. F., Rheingold, A. L., and I. A. Guzei, Carbon-sulfur bond-forming reductive elimination involving sp-, sp2-, and sp3-hybridized carbon. Mechanism, steric effects, and electronic effects on sulfide formation. Journal of the American Chemical Society, 1998. 120 (36): p. 9205-9219.
[doi]Hartwig, J. F., Richards, S., Baranano, D., and F. Paul, Influences on the relative rates for C-N bond-forming reductive elimination and beta-hydrogen elimination of amides. A case study on the origins of competing reduction in the palladium-catalyzed amination of aryl halides. Journal of the American Chemical Society, 1996. 118 (15): p. 3626-3633.
[doi]Louie, J. and J. F. Hartwig, A route to Pd-0 from Pd-II metallacycles in amination and cross-coupling chemistry. Angewandte Chemie-International Edition in English, 1996. 35 (20): p. 2359-2361.
Louie, J., F. Paul, and J. F. Hartwig, Catalysis with platinum-group alkylamido complexes, the active palladium amide in catalytic aryl halide aminations as deduced from kinetic data and independent generation. Organometallics, 1996. 15 (12): p. 2794-2805.
[doi]Mann, G. and J. F. Hartwig, Palladium alkoxides: Potential intermediacy in catalytic amination, reductive elimination of ethers, and catalytic etheration. Comments on alcohol elimination from Ir(III). Journal of the American Chemical Society, 1996. 118 (51): p. 13109-13110.
[doi]Baranano, D. and J. F. Hartwig, Carbon-Heteroatom Bond-Forming Reductive Elimination - Mechanism, Importance of Trapping Reagents, and Unusual Electronic Effects During Formation of Aryl Sulfides. Journal of the American Chemical Society, 1995. 117 (10): p. 2937-2938.
[first page][pdf]Driver, M. S. and J. F. Hartwig, A Rare, Low-Valent Alkylamido Complex, a Diphenylamido Complex, and Their Reductive Elimination of Amines by 3-Coordinate Intermediates. Journal of the American Chemical Society, 1995. 117 (16): p. 4708-4709.
[first page][pdf]Hartwig, J. F. and F. Paul, Oxidative Addition of Aryl Bromide after Dissociation of Phosphine from a 2-Coordinate Palladium(0) Complex, Bis(Tri-O-Tolylphosphine)Palladium(0). Journal of the American Chemical Society, 1995. 117 (19): p. 5373-5374.
[first page][pdf]Louie, J. and J. F. Hartwig, Transmetalation Involving Organotin Aryl, Thiolate, and Amide Compounds - an Unusual Type of Dissociative Ligand Substitution-Reaction. Journal of the American Chemical Society, 1995. 117 (46): p. 11598-11599.
[pdf]Paul, F., Patt, J., and J. F. Hartwig, Structural Characterization and Simple Synthesis of (Pd[P(O-Tol)3]2), Dimeric Palladium(II) Complexes Obtained by Oxidative Addition of Aryl Bromides, and Corresponding Monometallic Amine Complexes. Organometallics, 1995. 14(6): p. 3030-3039.
[first page][pdf]Paul, F., Patt, J., and J. F. Hartwig, Palladium-Catalyzed Formation of Carbon-Nitrogen Bonds - Reaction Intermediates and Catalyst Improvements in the Hetero Cross-Coupling of Aryl Halides and Tin Amides. Journal of the American Chemical Society, 1994. 116 (13): p. 5969-5970.
[first page][pdf]