Direct functionalization of nitrogen heterocycles via Rh-catalyzed C-H bond activation

Accounts of Chemical Research

Volumn 41, Issue 8, 2008, Pages 1013-1025

  Lewis, Jared C ^c   Bergman, Robert G ^a,b   Ellman, Jonathan A ^a,c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^c CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HETEROCYCLIC COMPOUND; HYDROGEN; NITROGEN; RHODIUM;

ARTICLE; CATALYSIS; CHEMISTRY;

CARBON; CATALYSIS; HETEROCYCLIC COMPOUNDS; HYDROGEN; NITROGEN; RHODIUM;

EID: 51649122191     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar800042p     Document Type: Article

References (67)

1. (a) Dyker, G. Transition Metal Catalyzed Coupling Reactions Under C-H Activation. Angew. Chem., Int. Ed. 1999, 38, 1698-1712.
2. (b) Kakiuchi, F.; Murai, S. Activation of CH Bonds: Catalytic Reactions. Top. Organomet. Chem. 1999, 3, 47-79.
3. (c) Miura, M.; Nomura, M. Direct Arylation via Cleavage of Activated and Unactivated C-H Bonds. Top. Curr. Chem. 2002, 219, 212-241.
4. (d) Campeau, L.-C.; Fagnou, K. Palladium-Catalyzed Direct Arylation of Simple Arenes in Synthesis of Biaryl Molecules. Chem. Commun. 2006, 1253-1264.
5. (e) Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q.-N.; Lazareva, A. Regioselective Functionalization of Unreactive Carbon-Hydrogen Bonds. Synlett. 2006, 20, 3382-3388.
6. (f) Alberico, D.; Scott, M. E.; Lautens, M. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation. Chem. Rev. 2007, 107, 174-238.
7. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH; New York, 1998.
8. (a) Crabtree, R. H. Alkane C-H Activation and Functionalization with Homogeneous Transition Metal Catalysts: a Century of Progress-a New Millennium in Prospect. Dalton 2001, 2437-2450.
9. (b) Bercaw, J. E.; Labinger, J. A. Understanding and Exploiting C-H Bond Activation. Nature 2002, 417, 507-514.
10. (c) Bergman, R. G. Organometallic Chemistry: C-H Activation. Nature 2007, 446, 391-393.
11. (a) Daugulis, O.; Zaitsev, V. G. Anilide Ortho-Arylation by Using C-H Activation Methodology. Angew. Chem., Int. Ed. 2005, 4, 4046-4048.
12. (b) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. Oxidative C-H Activation/C-C Bond Forming Reactions: Synthetic Scope and Mechanistic Insights. J. Am. Chem. Soc. 2005, 127, 7330-7331.
13. (c) Kakiuchi, F.; Murai, S. Catalytic C-H/Olefin Coupling. Acc. Chem. Res. 2002, 35, 826-834.
14. (a) Cho, J. -Y.; Iverson, C. N.; Smith, M. R. Steric and Chelate Directing Effects in Aromatic Borylation. J. Am. Chem. Soc. 2000, 122, 12868-12869.
15. (b) Ishiyama, T.; Takagi, J.; Kousaku, I.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. Mild Iridium-Catalyzed Borylation of Arenes. High Turnover Numbers, Room Temperature Reactions, and Isolation of a Potential Intermediate. J. Am. Chem. Soc. 2002, 124, 390-391.
16. (a) Tunge, J. A.; Foresee, L. N. Mechanistic Studies of Fujiwara Hydroarylation. C-H Activation versus Electrophilic Aromatic Substitution. Organometallics 2005, 24, 6440-6444.
17. (b) Yanagisawa, S.; Sudo, T.; Noyori, R.; Kami, K. Direct C-H Arylation of (Hetero)arenes with Aryl Iodides via Rhodium Catalysis. J. Am. Chem. Soc. 2006, 128, 11748-11749.
18. (c) Ferreira, E. M.; Stoltz, B. M. Catalytic C-H Bond Functionalization with Palladium(II): Aerobic Oxidative Annulations of Indoles. J. Am. Chem. Soc. 2003, 125, 9578-9579.
19. (d) Jia, C. G.; Piao, D. G.; Oyamada, J. Z.; Lu, W. J.; Kitamura, T.; Fujiwara, Y. Efficient Activation of Aromatic C-H Bonds for Addition to C-C Multiple Bonds. Science 2000, 287, 1992-1995.
20. (a) Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. Proton Abstraction Mechanism for the Palladium-Catalyzed Intramolecular Arylation. J. Am. Chem. Soc. 2006, 128, 1066-1067.
21. (b) Stuart, D. R.; Fagnou, K. The Catalytic Cross-Coupling of Unactivated Arenes. Science 2007, 316, 1172-1175.
22. Chen, M. S.; White, M. C. A Predictably Selective Aliphatic C-H Oxidation Reaction for Complex Molecule Synthesis. Science 2007, 318, 783-787.
23. Peters, M. W.; Meinhold, P.; Glieder, A.; Arnold, F. H. Regio- and Enantioselective Alkane Hydroxylation with Engineered Cytochromes P450 BM-3. J. Am. Chem. Soc. 2003, 125, 13442-13450.
24. Tan, K. L.; Bergman, R. G.; Ellman, J. A. Annulation of Alkenyl-Substituted Heterocycles via Rhodium-Catalyzed Intramolecular C-H Activated Coupling Reactions. J. Am. Chem. Soc. 2001, 123, 2685-2686.
25. Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Palladium-Catalyzed Arylation of Azole Compounds with Aryl Halides in the Presence of Alkali Metal Carbonates and the use of Copper Iodide in the Reaction. Bull. Chem. Soc. Jpn. 1998, 71, 467-473.
26. (a) Moore, E, J.; Pretzer, W. R.; O'Connel, T. J.; Harris, J.; LaBounty, L.; Cou, L.; Grimmer, S. S. Catalytic and Regioselective Acylation of Aromatic Heterocycles using Carbon Monoxide and Olefins. J. Am. Chem. Soc. 1992, 114, 5888-5890.
27. 12-Catalyzed Coupling of Heteroaromatic C-H/CO/Olefins. Regioselective Acylation of the Imidazole Ring. J. Am. Chem. Soc. 1996, 118, 493-494.
28. Ritleng, V.; Sirlin, C.; Pfeffer, M. Ru-, Rh-, and Pd-Catalyzed C-C Bond Formation Involving C-H Activation and Addition on Unsaturated Substrates: Reactions and Mechanistic Aspects. Chem. Rev. 2002, 102, 1731-1769.
29. (a) Tan, K. L.; Bergman, R. G.; Ellman, J. A. Intermolecular Coupling of Isomerizable Alkenes to Heterocycles via Rhodium-Catalyzed C-H Bond Activation. J. Am. Chem. Soc. 2002, 124, 13964-13965.
30. (b) Tan, K. L.; Park, S.; Ellman, J. A.; Bergman, R. G. Intermolecular Coupling of Alkenes to Heterocycles via C-H Bond Activation. J. Org. Chem. 2004, 69, 7329-7335.
31. Tan, K. L.; Vasudevan, A.; Bergman, R. G.; Ellman, J. A.; Souers, A. J. Microwave-Assisted C-H Bond Activation: A Rapid Entry into Functionalized Heterocycles. Org. Lett. 2003, 5, 2131-2134.
32. Larhed, M.; Moberg, C.; Hallberg, A. Microwave-Accelerated Homogeneous Catalysis in Organic Chemistry. Acc. Chem. Res. 2002, 35, 717-727.
33. Graczyk, P. P.; Khan, A.; Bhatia, G. S.; Palmer, V.; Medland, D.; et al. The Neuroprotective Action of JNK3 Inhibitors Based on the 6,7-Dihydro-5H- pyrrolo-[1,2-a]imidazole Scaffold. Bioorg. Med. Chem. Lett. 2005, 15, 4666-4670.
34. Rech, J. C.; Yato, M.; Duckett, D.; Ember, B.; LoGrasso, P. V.; Bergman, R. G.; Ellman, J. A. Synthesis of Potent Bicyclic Bisarylimidazole c-Jun N-Terminal Kinase inhibitors by Catalytic C-H Bond Activation. J. Am. Chem. Soc. 2007, 129, 490-491.
35. Tan, K. L.; Bergman, R. G.; Ellman, J. A. Intermediacy of an N- Heterocyclic Carbene Complex in the Catalytic C-H Activation of a Substituted Benzimidazole. J. Am. Chem. Soc. 2002, 124, 3202-3203.
36. Lewis, J. C.; Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Arylation of Heterocycles via Rhodium-Catalyzed C-H Bond Functionalization. Org. Lett. 2004, 6, 35-38.
37. Wiedemann, S. H.; Lewis, J, C.; Bergman, R. G.; Ellman, J. A. Experimental and Computational Studies on the Mechanism of N-Heterocycle C-H Activation by Rh(I). J. Am. Chem. Soc. 2006, 128, 2452-2462.
38. Gribble, M.; Ellman, J. A.; Bergman, R. G. Synthesis of a Benzodiazepine-derived Rhodium NHC Complex by C-H Bond Activation. Organometallics 2008, 27, 2152-2155.
39. Herrmann, W. A. N-Heterocyclic Carbenes. Part 31. N-Heterocyclic Carbenes: A New Concept in Organometallic Catalysis. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
40. For a more recent example, see: Clement, N. D.; Cavell, K. J. Transition-Metal-Catalyzed Reactions Involving Imidazolium Salt/N-Heterocyclic Carbene Couples as Substrates. Angew. Chem., Int. Ed. 2004, 43, 3845-3847.
41. 5) Moiety: Insight into Stereoelectronic Differences between Unsaturated and Saturated NHC Ligands. Organometallics 2003, 22, 4322-4326.
42. (a) Alvarez, E.; Conejero, S.; Paneque, M.; Petronilho, A.; Poveda, M. L.; Serrano, O.; Carmona, E. Iridium(III)-Induced Isomerization of 2-Substituted Pyridines to N-Heterocyclic Carbenes. J. Am. Chem. Soc. 2006, 128, 13060-13061.
43. (b) Esteruelas, M. A.; Fernandez-Alvarez, F. J.; Onate, E. Stabilization of NH Tautomers of Quinolines by Osmium and Ruthenium. J. Am. Chem. Soc. 2006, 128, 13044-13045.
44. Canac, Y.; Soleilhavoup, M.; Conejero, S.; Bertrand, G. Stable Non-N-Heterocyclic Carbenes (Non-NHC): Recent Progress. J. Organomet. Chem. 2004, 689, 3857-3865.
45. Wiedemann, S. H.; Ellman, J. A.; Bergman, R. G. Rhodium-Catalyzed Direct C-H Addition of 3,4-Dihydroquinazolines to Alkenes and Their Use in the Total Synthesis Of Vasicoline. J. Org. Chem. 2006, 71, 1969-1976.
46. Studies of these alkaloids has been reviewed comprehensively and continue to be reviewed annually. (a) Johne, S. In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Sainsbury, M., Ed.; Elsevier; Amsterdam, 2000; Supplement 2, Vol. IV I/J, pp 203-231.
47. (b) Michael, J. P. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 2007, 24, 223-246.
48. 2-Eliminations Under the Influence of Electrophiles. Part 14. Synthesis of 3,4-Dihydroquinazolines via Cyclic N-Diazonium Ions. Heterocycles 1981, 16, 1693-1696.
49. (b) Zharekeev, B. K.; Telezhenetskaya, M. V.; Khashimov, K. N.; Yunusov, S. Y. Reduction of Some Alkaloids of Peganum harmala by Sodium Tetrahydroborate. Khim. Prir. Soedin. 1974, 679-680.
50. (a) Klingler, R. J.; Chen, M. J.; Rathke, J. W.; Kramarz, K. W. Phosphines on the Thermodynamics of the Cobalt-Catalyzed Hydroformylation System. Organometallics 2007, 26, 352-357.
51. (b) Dwyer, C. L.; Kirk, M. M.; Meyer, W. H.; Janse van Rensburg, W.; Forman, G. S. Rotational Isomerism of a Phoban-Derived First-Generation Grubbs Catalyst. Organometallics 2006, 25, 3806-3812.
52. Gant, T. G.; Meyers, A. I. The Chemistry of 2-Oxazolines (1985-Present). Tetrahedron 1994, 50, 2297-2360.
53. Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Rhodium-Catalyzed Direct C-H Addition of 4,4-Dimethyl-2-oxazoline to Alkenes. Org. Lett. 2004, 6, 1685-1687.
54. Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Rh(I)-Catalyzed Alkylation of Quinolines and Pyridines via C-H Bond Activation. J. Am. Chem. Soc. 2007, 129, 5332-5333.
55. Hlasta, D. J.; Zificsak, C. A. Current Methods for the Synthesis of 2-Substituted Azoles. Tetrahedron 2004, 60, 8991-9016.
56. (a) See refs 1a, c, d, and f.
57. (b) Do, R-Q.; Daugulis, I. Copper-Catalyzed Arylation of Heterocycle C-H Bonds. J. Am. Chem. Soc. 2007, 129, 12404-12405.
58. (c) Chiong, H. A.; Daugulis, O. Palladium-Catalyzed Arylation of Electron-Rich Heterocycles with Aryl Chlorides. Org. Lett. 2007, 9, 1449-1451.
59. (d) Bellina, F.; Calandri, C.; Cauteruccio, S.; Rossi, R. Efficient and Highly Regioselective Direct C-2 Arylation of Azoles, Including Free (NH)-Imidazole, -Benzimidazole and -Indole, with Aryl Halides. Tetrahedron 2007, 63, 1970-1980.
60. Alonso, F.; Beletskaya, I. P.; Yus, M. Metal-Mediated Reductive Hydrodehalogenation of Organic Halides. Chem. Rev. 2002, 102, 4009-4091.
61. 2 as Catalyst Precursor. Organometallics 1995, 14, 1082-1084.
62. Lewis, J. C.; Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Microwave-Promoted Rhodium-Catalyzed Arylation of Heterocycles Through C-H Bond Activation. Angew. Chem., Int. Ed. 2006, 118, 1619-1621.
63. Johnson, J. B.; Rovis, T. More than Bystanders: The Effects of Olefins on Transition-Metal-Catalyzed Cross-Coupling Reactions. Angew. Chem., Int. Ed. 2008, 47, 840- 871.
64. van Assema, S. G. A.; Ehlers, A. W.; deKanter, F. J. J.; Schakel, M.; Spek, A. L.; Lutz, M.; Lammertsma, K. Bidentate Phosphorus Baskets by Intramolecular Phosphinidene Addition. Chem. - Eur. J. 2006, 12, 4333-4340.
65. Lewis, J. C.; Berman, A.; Bergman, R. G.; Ellman, J. A. Rh(I)-Catalyzed Arylation of Heterocycles via C-H Bond Activation: Expanded Scope through Mechanistic Insight. J. Am. Chem. Soc. 2008, 130, 2493-2500.
66. Chang, L. L.; Sidler, K. L.; Cascieri, M. A.; de Laszlo, S.; Koch, G.; Li, B.; MacCoss, M.; Mantlo, N.; O'Keefe, S.; Pang, M.; Rolando, A.; Hagmann, W. K. Substituted Imidazoles as Glucagon Receptor Antagonists. Bioorg. Med. Chem. Lett. 2001, 11, 2549-2553.
67. Netherton, M. R.; Fu, G. C. Air-Stable Trialkylphosphonium Salts: Simple, Practical, and Versatile Replacements for Air-Sensitive Trialkylphosphines. Applications in Stoichiometric and Catalytic Processes. Org. Lett. 2001, 3, 4295-4298.