1. C-C Bond Forming Cross-Couplings

   1a. Methods

Ge, S.; Hartwig, J.F. “Nickel-catalyzed Asymmetric α-Arylation and Heteroarylation of Ketones with Chloroarenes: Effect of Halide on Selectivity, Oxidation State and Room Temperature Reactions” J. Am. Chem. Soc. 2011, 133, 16330-16333. [doi] NIHMSID # 328258

Morimoto, H.; Tsubogo, T.; Litvinas, N.D.; Hartwig, J.F. “A Broadly Applicable Copper Reagent for Trifluoromethylations and Perfluoroalkylations of Aryl Iodides and Bromides” Angew. Chem. Int. Ed. 2011, 50, 3793–3798.

Huang, D.S.; DeLuca, R. J.; Hartwig, J.F. “α-Arylation of Esters Catalyzed by the Pd(I) Dimer [P(t-Bu)3]Pd(m-Br)]2” Org. Synth. 2011 88, 4-13. [PDF]

Liao, X.; Stanley, L.M.; Hartwig, J.F. “Enantioselective Total Syntheses of (−)-Taiwaniaquinone H and (−)-Taiwaniaquinol B by Iridium-Catalyzed Borylation and Palladium-Catalyzed Asymmetric α-Arylation” J. Am. Chem. Soc. 2011 ASAP. [doi]

Huang, D.S.; Hartwig, J.F. “Palladium-Catalyzed γ-Arylation of α,β-Unsaturated Esters from Silyl Ketene Acetals” Angew. Chem. Int. Ed. 2010 49, 5757-5761 (designated as a “Hot Paper”). [doi]

Vo, G.D., and J. F. Hartwig, Palladium-Catalyzed a-Arylation of Aldehydes with Bromo- and Chloroarenes Catalyzed by [Pd(allyl)Cl]2 and DPPF or Q-phos. Angew. Chem. Int. Ed. 2008, 47, 2127-2130. [doi]

Liao, X., Weng, Z., and J. F. Hartwig, Enantioselective-Arylation of Ketones with Aryl Triflates Catalyzed by Difluorphos Complexes of Palladium and Nickel. J. Am. Chem. Soc. 2008, 130,195-200. [doi]

Hama, T., and J. F. Hartwig, Palladium-Catalyzed α-Arylation of Esters with Chloroarenes. Org. Lett. 2008 10, 1549-1552. [doi]

Hama, T., and J. F. Hartwig, α-Arylation of Esters Catalyzed by the Pd(I) Dimer {[P(t-Bu)3]PdBr}2. Org. Lett. 2008, 10, 1545-1548. [doi]

Takemiya, A., and J. F. Hartwig, Palladium-Catalyzed Synthesis of Aryl Ketones by Coupling of Aryl Bromides with an Acyl Anion Equivalent. J. Am. Chem. Soc., 2006, 128, 14800-14801.
[doi]

Su, W.; Raders, S.; Verkade, J.G.; Liao, X; Hartwig, J.F., Palladium-Catalyzed α-Arylation of Trimethylsilyl Enol Ethers with Aryl Bromides and Chlorides. A Synergistic Effect of Two Metal Fluorides as Additives. Angew. Chem., 2006,. 45, 5852-5855. [doi]

Hama, T., Culkin, D. A., and J. F. Hartwig, Palladium-Catalyzed Intermolecular α-Arylation of Zinc Amide Enolates under Mild Conditions. J. Am. Chem. Soc., 2006,128, 4976-4985. [doi]

Limmert, M. E., Roy, A. H., and J. F. Hartwig, Kumada Coupling of Aryl and Vinyl Tosylates under Mild Conditions. J. Org. Chem., 2005,127, 9364-9370. [doi]

Wu, L. and J. F. Hartwig, Mild Palladium-Catalyzed Selective Monoarylation of Nitriles. J. Am. Chem. Soc., 2005, 127, 15824-15832. [doi]

Leitner, A., Larsen, J., Steffens, C. and J. F. Hartwig, Palladium-Catalyzed Addition of Mono- and Dicarbonyl Compounds to Conjugated Dienes. Journal of Organic Chemistry, 2004, 69, 7552-7557. [doi]

Liu, X. and J. F. Hartwig, Palladium-Catalyzed α-Arylation of Trimethylsilyl Enolates of Esters and Imides. High Functional Group Tolerance and Stereoselective Synthesis of α-Aryl Carboxylic Acid Derivatives. Journal of the American Chemical Society, 2004, 126, 5182-5191. [doi]

Culkin, D. A. and J. F. Hartwig, Palladium-catalyzed α-arylation of carbonyl compounds and nitriles. Accounts of Chemical Research, 2003, 36, 234-245. [doi]

Hama, T., Liu, X., Culkin, D. A., and J. F. Hartwig, Palladium-Catalyzed α-Arylation of Esters and Amides under More Neutral Conditions. Journal of the American Chemical Society, 2003, 125, 11176-11177. [doi]

Roy, A. H. and J. F. Hartwig, Oxidative Addition of Aryl Tosylates to Palladium(0) and Coupling of Unactivated Aryl Tosylates at Room Temperature. Journal of the American Chemical Society, 2003, 125, 8704-8705. [doi]

Beare, N. A. and J. F. Hartwig, Palladium-catalyzed arylation of malonates and cyanoesters using sterically hindered trialkyl- and ferrocenyldialkylphosphine ligands. Journal of Organic Chemistry, 2002, 67, 541-555. [doi]

Culkin, D. A. and J. F. Hartwig, Synthesis, characterization, and reactivity of arylpalladium cyanoalkyl complexes: Selection of catalysts for the alpha-arylation of nitriles. Journal of the American Chemical Society, 2002, 124, 9330-9331. [doi]

Jorgensen, M., Lee, S., Liu, X., Wolkowski, J. P., and J. F. Hartwig, Efficient synthesis of a-aryl esters by room-temperature palladium-catalyzed coupling of aryl halides with ester enolates. Journal of the American Chemical Society, 2002, 124, 12557-12565. [doi]

Kataoka, N., Shelby, Q., Stambuli, J. P., and J. F. Hartwig, Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C-C, C-N, and C-O bond-forming cross-couplings. Journal of Organic Chemistry, 2002, 67, 5553-5566. [doi]

Stambuli, J. P., Kuwano, R., and J. F. Hartwig, Unparalleled rates for the activation of aryl chlorides and bromides: Coupling with amines and boronic acids in minutes at room temperature. Angewandte Chemie-International Edition, 2002, 41, 4746-4748. [abstract][pdf]

Wolkowski, J. P. and J. F. Hartwig, Generation of Reactivity from Typically Stable Ligands: C-C Bond-Forming Reductive Elimination from Aryl Palladium(II) Complexes of Malonate Anions. Angewandte Chemie-International Edition, 2002, 114, 4465-4467. [abstract][pdf]

Culkin, D. A. and J. F. Hartwig, C-C bond-forming reductive elimination of ketones, esters, and amides from isolated arylpalladium(II) enolates. Journal of the American Chemical Society, 2001, 123, 5816-5817. [doi]

Lee, S. and J. F. Hartwig, Improved catalysts for the palladium-catalyzed synthesis of oxindoles by amide a-arylation. Rate acceleration, use of aryl chloride substrates, and a new carbene ligand for asymmetric transformations. Journal of Organic Chemistry, 2001, 66, 402-3415. [doi]

Lee, S., Beare, N. A., and J. F. Hartwig, Palladium-catalyzed alpha-arylation of esters and protected amino acids. Journal of the American Chemical Society, 2001. 123, 8410-8411. [doi]

Stambuli, J. P., Stauffer, S. R., Shaughnessy, K. H., and J. F. Hartwig, Screening of homogeneous catalysts by fluorescence resonance energy transfer. Identification of catalysts for room-temperature Heck reactions. Journal of the American Chemical Society, 2001, 123, 2677-2678. [doi]

Stauffer, S. R., Beare, N .A., Stambuli, J. P., and J. F. Hartwig, Palladium-catalyzed arylation of ethyl cyanoacetate. Fluorescence resonance energy transfer as a tool for reaction discovery. Journal of the American Chemical Society, 2001, 123, 4641-4642. [doi]

Kawatsura, M. and J. F. Hartwig, Simple, highly active palladium catalysts for ketone and malonate arylation: Dissecting the importance of chelation and steric hindrance. Journal of the American Chemical Society, 1999, 121, 1473-1478. [doi]

Shaughnessy, K. H., Kim, P., and J. F. Hartwig, A fluorescence-based assay for high-throughput screening of coupling reactions. Application to Heck chemistry. Journal of the American Chemical Society, 1999, 121, 2123-2132. [doi]

Shaughnessy, K. H., Hamann, B. C., and J. F. Hartwig, Palladium-catalyzed inter- and intramolecular alpha-arylation of amides. Application of intramolecular amide arylation to the synthesis of oxindoles. Journal of Organic Chemistry, 1998, 63, 6546-6553. [doi]

Hamann, B. C. and J. F. Hartwig, Palladium-catalyzed direct alpha-arylation of ketones. Rate acceleration by sterically hindered chelating ligands and reductive elimination from a transition metal enolate complex. Journal of the American Chemical Society, 1997, 119, 12382-12383. [doi]