Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides

Accounts of Chemical Research

Volumn 41, Issue 11, 2008, Pages 1534-1544

  Hartwig, John F ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; HALOGEN; LIGAND; PALLADIUM; SULFIDE;

AMINATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; REVIEW;

AMINATION; AMMONIA; CATALYSIS; HALOGENS; LIGANDS; MOLECULAR STRUCTURE; PALLADIUM; SULFIDES;

EID: 57549097790     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar800098p     Document Type: Review

References (66)

1. de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1.
2. For our first paper on this topic, see: Paul, F.; Patt, J.; Hartwig, J. F. Palladium-Catalyzed Formation of Carbon-Nitrogen Bonds. Reaction Intermediates and Catalyst Improvements in the Hetero Cross-Coupling of Arylhalides and Tin Amides. J. Am. Chem. Soc. 1994, 116, 5969-5970.
3. For contemporaneous work, see: Guram, A. S.; Buchwald, S. L. Palladium-Catalyzed Aromatic Aminations with In Situ Generated Aminostannanes. J. Am. Chem. Soc. 1994, 116, 7901-7902.
4. Hamann, B. C.; Hartwig, J. F. Palladium-Catalyzed Direct Arylation of Ketones. Sterically Hindered Phosphines Enhance Reaction Yields. J. Am. Chem. Soc. 1997, 119, 12382-12383.
5. For contemporaneous work on this reaction, see: Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Palladium-Catalyzed Regioselective Mono-and Diarylation Reactions of 2-Phenylphenols and Naphthols with Aryl Halides. Angew. Chem., Int. Ed. Engl. 1997, 36, 1740-1742.
6. Palucki, M.; Buchwald, S. L. Palladium-Catalyzed α-Arylation of Ketones. J. Am. Chem. Soc. 1997, 119, 11108-11109.
7. Shekhar, S.; Shen, Q.; Barrios-Landeros, F.; Hartwig, J. F. Synthesis of Anilines. In The Chemistry of Anilines; Rapoport, Z., Ed.; Wiley Interscience: New York, 2007; pp 455-536.
8. Hartwig, J. F. Palladium-Catalyzed Synthesis of Aryl Ethers and Related Compounds Containing S and Se. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E. I., Ed.; Wiley-Interscience: New York, 2002; Vol. 1, pp 1097-1106.
9. Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. Top. Curr. Chem. 2002, 219, 131-209.
10. Culkin, D. A.; Hartwig, J. F. Palladium-Catalyzed β-Arylation of Carbonyl Compounds and Nitriles. Acc. Chem. Res. 2003, 36, 234-245.
11. Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Synthesis, Characterization, and Crystal Structures of Monomeric and Dimeric Palladium(II) Amide Complexes. Organometallics 1994, 13, 3921-3931.
12. Hartwig, J. F. Electronic Effects on Reductive Elimination to Form Carbon-Carbon and Carbon-heteroatom Bonds from Palladium(II) Complexes. Inorg. Chem. 2007, 46, 1936-1947.
13. Kosugi, M.; Kameyama, M.; Migita, T. Palladium-Catalyzed Aromatic Amination of Aryl Bromides with Diethylamino-tributyltin. Chem. Lett. 1983, 927-928.
14. Guram, A. S.; Rennels, R. A.; Buchwald, S. L. A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
15. Louie, J.; Hartwig, J. F. Palladium-Catalyzed Synthesis of Arylamines from Aryl Halides. Mechanistic Studies Lead to Coupling in the Absence of Tin Reagents. Tetrahedron Lett. 1995, 36, 3609-3612.
16. Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. An Improved Catalyst System for Aromatic Carbon-Nitrogen Bond Formation: The Possible Involvement of Bis (Phosphine) Palladium Complexes as Key Intermediates. J. Am. Chem. Soc. 1996, 118, 7215-7216.
17. 2. J. Am. Chem. Soc. 1996, 118, 7217-7218.
18. Wolfe, J. P.; Buchwald, S. L. Scope and Limitation of the Pd/BINAP-catalyzed Amination of Aryl Bromides. J. Org. Chem. 2000, 65, 1144-1157.
19. Hamann, B. C.; Hartwig, J. F. Sterically Hindered Alkyl Phosphine Ligands Greately Accelerate the Palladium-Catalyzed Amination of Aryl Iodides, Bromides, Chlorides, and Tosylates. J. Am. Chem. Soc. 1998, 120, 7369-7370.
20. Spindler, F.; Wirth-Tijani, A.; Landert, H. Preparation of ferrocenyldiphosphines as ligands for homogeneous catalysis. EP 612758 A1 19940831, 1994.
21. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Rational Development of Practical Catalysts for Aromatic Carbon-Nitrogen Bond Formation. Acc. Chem. Res. 1998, 31, 805-818.
22. Nishiyama, M.; Yamamoto, T.; Koie, Y. Synthesis of N-Arylpiperazines from Aryl Halides and Piperazine under a Palladium Tri-tert-butylphosphine Catalyst. Tetrahedron Lett. 1998, 39, 617-620.
23. Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. Room-Temperature Palladium-Catalyzed Amination of Aryl Bromides and Chlorides and Extended Scope of Aromatic C-N Bond Formation with a Commercial Ligand. J. Org. Chem. 1999, 64, 5575-5580.
24. Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Unparalleled Rates for the Activation of Aryl Chlorides. Coupling with Amines and Boronic Acids in Minutes at Room Temperature. Angew. Chem., Int. Ed. 2002, 41, 4746-4747.
25. Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. F. Unusual in situ Ligand Modification to Generate a Catalyst for Room Temperature Aromatic C-O Bond Formation. J. Am. Chem. Soc. 2000, 122, 10718-10719.
26. Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. Air Stable, Sterically Hindered Ferrocenyl Dialkylphosphines for Palladium-Catalyzed C-C, C-N and C-O Bond-Forming Cross-Couplings. J. Org. Chem. 2002, 67, 5553-5566.
27. Liu, X.; Hartwig, J. F. Palladium-Catalyzed Arylation of Trimethylsilyl Enolates of Esters and Imides. High Functional Group Tolerance and Stereoselective Synthesis of α-Aryl Carboxylic Acid Derivatives. J. Am. Chem. Soc. 2004, 126, 5182-5191.
28. Hama, T.; Culkin, D. A.; Hartwig, J. F. Palladium-Catalyzed Intermolecular α-Arylation of Zinc Amide Enolates under Mild Conditions. J. Am. Chem. Soc. 2006, 128, 4976-4985.
29. 2. Org. Lett. 2008, 10, 1545-1548.
30. Hama, T.; Hartwig, J. F. Palladium-Catalyzed α-Arylation of Esters with Chloroarenes. Org. Lett. 2008, 10, 1549-1552.
31. Su, W.; Raders, S.; Verkade, J. G.; Liao, X.; Hartwig, J. F. Palladium-Catalyzed alpha-Arylation of Trimethylsilyl Enol Ethers with Aryl Bromides and Chlorides. A Synergistic Effect of Two Metal Fluorides as Additives. Angew. Chem., Int. Ed. 2006, 45, 5852-5855.
32. Harkal, S.; Rataboul, F.; Zapf, A.; Fuhrmann, C.; Riermeier, T.; Monsees, A.; Beller, M. "Dialkylphosphinoimidazoles as New Ligands for Palladium-Catalyzed Coupling Reactions of Aryl Chlorides. Adv. Synth. Catal. 2004, 346, 1742-1748.
33. Nolan, S. P. Well-Defined (NHC)Palladium(II) Precatalysts for Cross-Coupling Reactions. Acc. Chem. Res. 2008, 41, 1440-1449.
34. Blaser, H. U.; Schmidt, E. Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions; Wiley-VCH: Weinheim, Germany, 2004.
35. For an exception, see: Magerlein, W.; Indolese, A. F.; Beller, M. Development of New Palladium Catalysts for the Alkoxycarbonylation of Aryl Chlorides. J. Organomet. Chem. 2002, 641, 30-40.
36. Paul, F.; Patt, J.; Hartwig, J. F. Structural Characterization and Simple Synthesis of Bis-o-tolylphopshine Palladium(0). Characterization of the Dimeric Palladium(II) Complexes Obtained by Oxidative Addition of Aryl Bromides and Their Reactivity with Amines. Organometallics 1995, 14, 3030-3039.
37. Wagaw, S.; Buchwald, S. L. The Synthesis of Aminopyridines: A Method Employing Palladium-Catalyzed Carbon-Nitrogen Bond Formation. J. Org. Chem. 1996, 61, 7240-7241.
38. Shen, Q.; Shekhar, S.; Stambuli, J. P.; Hartwig, J. F. Highly Reactive, General, and Long-Lived Catalysts for Coupling Heteroaryl and Aryl Chlorides with Primary Nitrogen Nucleophiles. Angew. Chem., Int. Ed. 2004, 44, 1371-1375.
39. Shen, Q.; Ogata, T.; Hartwig, J. F. 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.
40. Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J. J.; Buchwald, S. L. Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, And Triflates. J. Org. Chem. 2000, 65, 1158-1174.
41. Harris, M. C.; Huang, X.; Buchwald, S. L. Improved Functional Group Compatibility in the Palladium-Catalyzed Synthesis of Aryl Amines. Org. Lett. 2002, 4, 2885-2888.
42. Huang, X. H.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. "Expanding Pd-Catalyzed C-N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions. J. Am. Chem. Soc. 2003, 125, 6653-6655.
43. Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki-Miyaura and Buchwald-Hartwig Reactions. J. Am. Chem. Soc. 2006, 128, 4101-4111.
44. Anderson, K. W.; Tundel, R. E.; Ikawa, T.; Altman, R. A.; Buchwald, S. L. Monodentate Phosphines Provide Highly Active Catalysts for Pd-Catalyzed C-N Bond-Forming Reactions of Heteroaromatic Halides/Amines and (H)N-Heterocycles. Angew. Chem., Int. Ed. 2006, 45, 6523-6527.
45. Wolfe, J. P.; Buchwald, S. L. Palladium-Catalyzed Amination of Aryl Iodides. J. Org. Chem. 1996, 61, 1133-1135.
46. 3N: An effective Ligand in the Palladium-Catalyzed Amination of Aryl Bromides and Iodides. J. Org. Chem. 2003, 68, 452-459.
47. Shen, Q.; Hartwig, J. F. Palladium-Catalyzed Coupling of Ammonia and Lithium Amide. J. Am. Chem. Soc. 2006, 128, 10028-10029.
48. Surry, D. S.; Buchwald, S. L. Selective Palladium-Catalyzed Arylation of Ammonia: Synthesis of Anilines as Well as Symmetrical and Unsymmetrical Di- and Triarylamines. J. Am. Chem. Soc. 2007, 129, 10354-10355.
49. Barañano, D.; Hartwig, J. F. Carbon-Heteroafom Bond Forming Reductive Elimination. Importance of Trapping Reagents and Unusual Electronic Effects in the Formation of Arylsulfides. J. Am. Chem. Soc. 1995, 117, 2937-2938.
50. 3-Hybridized Carbon. Mechanism, Steric Effects, and Electronic Effects on Sulfide Formation. J. Am. Chem. Soc. 1998, 120, 9205-9219.
51. Kosugi, M.; Shimizu, T.; Migita, T. Reactions of Aryl Halides with Thiolate Anions in the Presence of Catalytic Amounts of Tetrakis(triphenylphosphine) Palladium. Chem. Lett. 1978, 13-14.
52. Murata, M.; Buchwald, S. L. A General and Efficient Method for the Palladium-Catalyzed Cross-Coupling of Thiols and Secondary Phosphines. Tetrahedron 2004, 60, 7397-7403.
53. Fernandez-Rodriguez, M. A.; Shen, Q. L.; Hartwig, J. F. A General and Long-Lived Catalyst for the Palladium-Catalyzed Coupling of Aryl Halides with Thiols. J. Am. Chem. Soc. 2006, 128, 2180-2181.
54. Fernandez-Rodriguez, M. A.; Shen, Q. L.; Hartwig, J. F. Highly efficient and Functional-Group-Tolerant Catalysts for the Palladium-Catalyzed Coupling of Aryl Chlorides with Thiols. Chem. - Eur. J. 2006, 12, 7782-7796.
55. 2, by Oxidative Addition of Diaryl Disulfides to Ni(0) Complexes and Ni-Catalyzed Coupling Reactions between Thiophenols and Aryl Halides. Inorg. Chim. Acta 1984, 83, 47-53.
56. 3 as solvent.
57. Kreis, M.; Bräse, S. A General and Efficient Method for the Synthesis of Silyl-Protected Arenethiols from Aryl Halides or Triflates. Adv. Synth. Catal. 2004, 347, 313-319.
58. Hartwig, J. F. Carbon-Heteroatom Bond-Forming Reductive Elimination of Amines, Ethers, and Sulfides. Acc. Chem. Res. 1998, 31, 852-860.
59. Hartwig, J. F. Transition Metal-Catalyzed Synthesis of Arylamines and Arylethers from Aryl Halides or Triflates. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046-2067.
60. Roy, A. H.; Hartwig, J. F. Oxidative Addition of Aryl Tosylates to Palladium(0) and Coupling of Unactivated Aryl Tosylates at Room Temperature. J. Am. Chem. Soc. 2003, 125, 8704-8705.
61. Driver, M. S.; Hartwig, J. F. Carbon-Nitrogen Bond-Forming Reductive Elimination of Arylamines from Pd(II). J. Am. Chem. Soc. 1997, 119, 8232-8245.
62. Fujita, K. I.; Yamashita, M.; Puschmann, F.; Alvarez-Falcon, M. M.; Incarvito, C. D.; Hartwig, J. F. Organometallic Chemistry from Amidate Complexes. Reductive Elimination of N-Aryl Amidates from Palladium(II). J. Am. Chem. Soc. 2006, 128, 9044-9045.
63. Yamashita, M.; Hartwig, J. F. Synthesis, Structure, and Reductive Elimination Chemistry of Three-Coordinate Arylpalladium Amido Complexes. J. Am. Chem. Soc. 2004, 126, 5344-5345.
64. Stambuli, J. R.; Weng, Z. Q.; Incarvito, C. D.; Hartwig, J. F. Reductive Elimination of Ether from T-Shaped, Monomeric Arylpalladium Alkoxides. Angew. Chem., Int. Ed. 2007, 46, 7674-7677.
65. Widenhoefer, R. A.; Buchwald, S. L. Electronic Dependence of C-O Reductive Elimination from Palladium (Aryl)neopentoxide Complexes. J. Am. Chem. Soc. 1998, 120, 6504-6511.
66. Culkin, D. A.; Hartwig, J. F. Carbon-Carbon Bond-Forming Reductive Elimination from Arylpalladium Complexes Containing Functionalized Alkyl Groups. Influence of Ligand Steric and Electronic Properties on Structure, Stability, and Reactivity. Organometallics 2004, 23, 3398-3416.