2. C-X Bond Forming Cross-Couplings

   2a. Methods

Fernandez-Rodriguez, M.A.; Hartwig, J.F. “One-Pot Synthesis of Unsymmetrical Diaryl Thioethers by Palladium-Catalyzed Coupling of Two Aryl Bromides and a Thiol Surrogate” Chem.—Eur. J. 2010, 16, 2355-2359. [doi]

Vo, G. D.; Hartwig, J. F. Palladium-Catalyzed Coupling of Ammonia with Aryl Chlorides, Bromides, Iodides, and Sulfonates: A General Method for the Preparation of Primary Arylamines. J. Am. Chem. Soc. 2009, 131, 11049-11061. [doi]

Fernández-Rodríguez, M.A.; Hartwig, J.F. A General, Efficient, and Functional-Group-Tolerant Catalyst System for the Palladium-Catalyzed Thioetherification of Aryl Bromides and Iodides J. Org. Chem. 2009, 74, 1663-1672. [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]

Ogata, T.; Hartwig, J.F. Palladium-Catalyzed Amination of Aryl and Heteroaryl Tosylates at Room Temperature J. Am. Chem. Soc. (Communication) 2008, 130, 13848-13849. [doi]

Shen, Q., Ogata, T., and J. F. Hartwig, Highly Reactive, General and Long-Lived Catalysts for Palladium-Catalyzed Amination of Heteroaryl and Aryl Chlorides, Bromides and Iodides: Scope and Structure-Activity Relationships. J. Am. Chem. Soc. 2008 130, 6586-6596. [doi]

Shen, Q. and J. F. Hartwig, Lewis Acid Acceleration of C-N Bond-Forming Reductive Elimination from Heteroarylpalladium Complexes and Catalytic Amidation of Heteroaryl Bromides. J. Amer. Chem. Soc, 2007. 129 7734-7735. [doi]

Fernandez-Rodríguez, M. A., Shen, Q., and J. F. Hartwig, Highly Efficient and Functional-Group-Tolerant Catalysts for the Palladium-Catalyzed Coupling of Aryl Chlorides with Thiols. Chem.--Eur. J. 2006 12, 7782-7796. [doi]

Shen, Q., and J. F. Hartwig, Palladium-Catalyzed Coupling of Ammonia and Lithium Amide with Aryl Halides. J. Am. Chem. Soc. 2006 128, 10028-10029. [doi]

Fernández-Rodríguez, M. A., Shen, Q., and J. F. Hartwig, A General and Long-Lived Catalyst for the Palladium-Catalyzed Coupling of Aryl Halides with Thiols. J. Am. Chem. Soc. 2006 128, 2180-2181. [doi]

Barrios-Landeros, F. and J. F. Hartwig, Distinct Mechanisms for the Oxidative Addition of Chloro-, Bromo-, and Iodoarenes to a Bisphosphine Palladium(0) Complex with Hindered Ligands. J. Am. Chem. Soc. 2005 127, 6944-6945. [doi]

Hooper, M. W., Utsunomiya, M., and J. F. Hartwig, Scope and mechanism of palladium-catalyzed amination of five-membered heterocyclic halides. Journal of Organic Chemistry 2003 68, 2861-2873. [doi]

Hooper, M. W. and J. F. Hartwig, Understanding the Coupling of Heteroaromatic Substrates: Synthesis, Structures, and Reductive Eliminations of Heteroarylpalladium Amido Complexes. Organometallics 2003 22, 3394-3403. [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]

Stauffer, S. R. and J. F. Hartwig, Fluorescence Resonance Energy Transfer (FRET) as a High-Throughput Assay for Coupling Reactions. Arylation of Amines as a Case Study. Journal of the American Chemical Sociey 2003 125, 6977-6985. [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]

Kuwano, R., Utsunomiya, M., and J. F. Hartwig, Aqueous hydroxide as a base for palladium-catalyzed amination of aryl chlorides and bromides. Journal of Organic Chemistry 2002 67, 6479-6486. [doi]

Ranasinghe, M. I., Varnavski, O. P., Pawlas, J., Hauck, S. I., Louie, J., Hartwig, J. F., and T. Goodson III, Femtosecond excitation energy transport in triarylamine dendrimers. Journal of the American Chemical Societ, 2002 124, 6520-6521. [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]

Lee, D.-Y. and J. F. Hartwig, Zinc Trimethylsilylamide as a Mild Ammonia Equivalent and Base for the Amination of Aryl Halides and Triflates. Org. Lett. 2005 7, 1169-1172. [doi]

Shen, Q., Shekhar, S., Stambuli, J. P., and J. F. Hartwig, Highly Reactive, General, and Long-Lived Catalysts for Coupling Heteroaryl and Aryl Chlorides with Primary Nitrogen Nucleophiles. Angewandte Chemie International Edition 2005 44, 1371-1375. [abstract]

Zhao, J., Goldman, A. S., and J. F. Hartwig, Oxidative Addition of Ammonia to Form a Stable Monomeric Amido Hydride Complex. Science 2005 307, 1080-1082. [link]

Bae, C., Hartwig, J. F., Boaen Harris, N. K., Long, R. O., Anderson, K. S., and M. A. Hillmyer, Catalytic Hydroxylation of Polypropylenes. J. Am. Chem. Soc. 2005 127, 767-776. [doi]

Shekhar, S. and J. F. Hartwig, Distinct Electronic Effects on Reductive Eliminations of Symmetrical and Unsymmetrical Bis-Aryl Platinum Complexes. Journal of the American Chemical Society 2004 126, 13016-13027. [doi]

Krug, C. and J. F. Hartwig, Reactions of an Arylrhodium Complex with Aldehydes, Imines, Ketones, and Alkynones. New Classes of Insertion Reactions. Organometallics 2004 23, 4594-4607. [doi]

Roy, A. H. and J. F. Hartwig, Reductive Elimination of Aryl Halides upon Addition of Hindered Alkylphosphines to Dimeric Arylpalladium(II) Halide Complexes. Organometallics, 2004. 23(7): p. 1533-1541.
[doi]

Yamashita, M. and J. F. Hartwig, Synthesis, Structure, and Reductive Elimination Chemistry of Three-Coordinate Arylpalladium Amido Complexes. Journal of the American Chemical Society, 2004. 126(17): p 5344-5345.
[doi]

Chae, H. K., Eddaoudi, M., Kim, J., Hauck, S. I., Hartwig, J. F., O'Keeffe, M., and O. M. Yaghi, Tertiary building units: Synthesis, structure, and porosity of a metal-organic dendrimer framework (MODF-1). Journal of the American Chemical Society, 2001. 123(46): p. 11482-11483.
[doi]

Lee, S., M. Jorgensen, and J. F. Hartwig, Palladium-catalyzed synthesis of arylamines from aryl halides and lithium bis(trimethylsilyl)amide as an ammonia equivalent. Organic Letters, 2001. 3(17): p. 2729-2732.
[doi]

Stauffer, S. R., Lee, S., Stambuli, J. P., Hauck, S. I., and J. F. Hartwig, High turnover number and rapid, room-temperature amination of chloroarenes using saturated carbene ligands. Organic Letters, 2000. 2(10): p. 1423-1426.
[doi]

Goodson, F. E., Hauck, S. I., and J. F. Hartwig, Palladium-catalyzed synthesis of pure, regiodefined polymeric triarylamines. Journal of the American Chemical Society, 1999. 121(33): p. 7527-7539.
[doi]

Hartwig, J. F., Kawatsura, M., Hauck, S. I., Shaughnessy, K. H., and L. M. Alcazar-Roman Room-temperature palladium-catalyzed amination of aryl bromides and chlorides and extended scope of aromatic C-N bond formation with a commercial ligand. Journal of Organic Chemistry, 1999. 64(15): p. 5575-5580.
[doi]

Hauck, S. I., Lakshmi, K. V. and J. F. Hartwig, Tetraazacyclophanes by palladium-catalyzed aromatic amination. Geometrically defined, stable, high-spin diradicals. Organic Letters, 1999. 1(13): p. 2057-2060.
[doi]

Mann, G., Incarvito, C. D., Rheingold, A. L., and J. F. Hartwig, Palladium-catalyzed C-O coupling involving unactivated aryl halides. Sterically induced reductive elimination to form the C-O bond in diaryl ethers. Journal of the American Chemical Society, 1999. 121(13): p. 3224-3225.
[doi]

Goodson, F. E. and J. F. Hartwig, Regiodefined poly(N-arylaniline)s and donor-acceptor copolymers via palladium-mediated amination chemistry. Macromolecules, 1998. 31(5): p. 1700-1703.
[doi]

Hamann, B. C. and J. F. Hartwig, Sterically hindered chelating alkyl phosphines provide large rate accelerations in palladium-catalyzed amination of aryl iodides, bromides, and chlorides, and the first amination of aryl tosylates. Journal of the American Chemical Society, 1998. 120(48): p. 12706-12706.
[doi]

Hartwig, J. F., Synthesis, structure, and reactivity of a palladium hydrazonato complex: A new type of reductive elimination reaction to form C-N bonds and catalytic arylation of benzophenone hydrazone. Angewandte Chemie-International Edition, 1998. 37(15): p. 2090-2093.
[abstract][pdf]

Louie, J. and J. F. Hartwig, The largest discrete oligo(m-aniline). An exponential growth strategy using palladium-catalyzed amination of aryl sulfonates. Macromolecules, 1998. 31(19): p. 6737-6739.
[doi]

Mann, G., Hartwig, J. F., Driver, M. S., and C. Fernandez-Rivas, Palladium-catalyzed C-N(sp2) bond formation: N-arylation of aromatic and unsaturated nitrogen and the reductive elimination chemistry of palladium azolyl and methyleneamido complexes. Journal of the American Chemical Society, 1998. 120(4): p. 827-828.
[doi]

Baranano, D., Mann, G., and J. F. Hartwig, Nickel and palladium-catalyzed cross-couplings that form carbon-heteroatom and carbon-element bonds. Current Organic Chemistry, 1997. 1(3): p. 287-305.

Louie, J., Hartwig, J. F., and A. J. Fry, Discrete high molecular weight triarylamine dendrimers prepared by palladium-catalyzed amination. Journal of the American Chemical Society, 1997. 119(48): p. 11695-11696.
[doi]

Louie, J., Driver, M. S., Hamann, B. C., and J. F. Hartwig, Palladium-catalyzed amination of aryl triflates and importance of triflate addition rate. Journal of Organic Chemistry, 1997. 62(5): p. 1268-1273.
[doi]

Mann, G. and J. F. Hartwig, Nickel- vs palladium-catalyzed synthesis of protected phenols from aryl halides. Journal of Organic Chemistry, 1997. 62(16): p. 5413-5418.
[doi]

Mann, G. and J. F. Hartwig, Palladium-catalyzed formation of diaryl ethers from aryl bromides. Electron poor phosphines enhance reaction yields. Tetrahedron Letters, 1997. 38(46): p. 8005-8008.
[abstract][pdf]

Driver, M. S. and J. F. Hartwig, A second-generation catalyst for aryl halide amination: Mixed secondary amines from aryl halides and primary amines catalyzed by (DPPF)PdCl2. Journal of the American Chemical Society, 1996. 118(30): p. 7217-7218.
[doi]

Louie, J. and J. F. Hartwig, Palladium-Catalyzed Synthesis of Arylamines from Aryl Halides - Mechanistic Studies Lead to Coupling in the Absence of Tin Reagents. Tetrahedron Letters, 1995. 36(21): p. 3609-3612.
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