Low-valent cobalt catalysis: New opportunities for C-H functionalization

Accounts of Chemical Research

Volumn 47, Issue 4, 2014, Pages 1208-1219

  Gao, Ke ^a   Yoshikai, Naohiko ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84898899948     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar400270x     Document Type: Article

References (76)

1. C-H Activation; Yu, J.-Q., Shi, Z.-J., Eds.; Topics in Current Chemistry, Vol. 292; Springer: Berlin, 2010.
2. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. C-H Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals Angew. Chem., Int. Ed. 2012, 51, 8960-9009
3. Kulkarni, A. A.; Daugulis, O. Direct Conversion of Carbon-Hydrogen into Carbon-Carbon Bonds by First-Row Transition-Metal Catalysis Synthesis 2009, 4087-4109
4. Wencel-Delord, J.; Dröge, T.; Liu, F.; Glorius, F. Towards Mild Metal-Catalyzed C-H Bond Activation Chem. Soc. Rev. 2011, 40, 4740-4761
5. Kleiman, J. P.; Dubeck, M. Preparation of Cyclopentadienyl [ o -(Phenylazo)Phenyl]Nickel J. Am. Chem. Soc. 1963, 85, 1544-1545
6. Cope, A. C.; Siekman, R. W. Formation of Covalent Bonds from Platinum or Palladium to Carbon by Direct Substitution J. Am. Chem. Soc. 1965, 87, 3272-3273
7. Murahashi, S. Synthesis of Phthalimidines from Schiff Bases and Carbon Monoxide J. Am. Chem. Soc. 1955, 77, 6403-6404
8. Halbritter, G.; Knoch, F.; Wolski, A.; Kisch, H. Functionalization of Aromatic Azo-Compounds by the Cobalt-Catalyzed, Regioselective Double Addition of Tolane: 2,6-Distilbenylazobenzenes and 2,3-Dihydrocinnolines Angew. Chem., Int. Ed. 1994, 33, 1603-1605
9. Lenges, C. P.; Brookhart, M. Co(I)-Catalyzed Inter- and Intramolecular Hydroacylation of Olefins with Aromatic Aldehydes J. Am. Chem. Soc. 1997, 119, 3165-3166
10. Lenges, C. P.; White, P. S.; Brookhart, M. Mechanistic and Synthetic Studies of the Addition of Alkyl Aldehydes to Vinylsilanes Catalyzed by Co(I) Complexes J. Am. Chem. Soc. 1998, 120, 6965-6979
11. 3 C-H Bonds with Cobalt(I): Catalytic Synthesis of Enamines J. Am. Chem. Soc. 2007, 129, 14544-14545
12. 5(L)Co] Moiety J. Organomet. Chem. 1997, 528, 199-203
13. 2-Azobenzene Ligands Z. Naturforsch. B 1993, 48, 778-784
14. Klein, H.-F.; Camadanli, S.; Beck, R.; Leukel, D.; Flörke, U. Cyclometalation of Substrates Containing Imine and Pyridyl Anchoring Groups by Iron and Cobalt Complexes Angew. Chem., Int. Ed. 2005, 44, 975-977
15. Camadanli, S.; Beck, R.; Flörke, U.; Klein, H.-F. First Regioselective Cyclometalation Reactions of Cobalt in Arylketones: C-H versus C-F Activation Dalton Trans. 2008, 5701-5704
16. Beck, R.; Sun, H.; Li, X.; Camadanli, S.; Klein, H.-F. Cyclometalation of Thiobenzophenones with Mononuclear Methyliron and -Cobalt Complexes Eur. J. Inorg. Chem. 2008, 3253-3257
17. Klein, H.-F.; Schneider, S.; He, M.; Flörke, U.; Haupt, H.-J. ortho-Metalation of Triarylphosphane at Cobalt and Template Synthesis of Chelating 2-(Diarylphosphanyl)aroyl Ligands Eur. J. Inorg. Chem. 2000, 2295-2301
18. Klein, H.-F.; Beck, R.; Flörke, U.; Haupt, H.-J. Five- and Six-Membered Cobaltocycles with C,P-Chelating Ligands through Regiospecific Cyclometalation of Mono(2-Substituted) Triphenylphosphane Eur. J. Inorg. Chem. 2003, 1380-1387
19. Kakiuchi, F.; Murai, S. Catalytic C-H/Olefin Coupling Acc. Chem. Res. 2002, 35, 826-834
20. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation Chem. Rev. 2010, 110, 624-655
21. Yoshikai, N. Cobalt-Catalyzed, Chelation-Assisted C-H Bond Functionalization Synlett 2011, 1047-1051
22. Gao, K.; Lee, P.-S.; Fujita, T.; Yoshikai, N. Cobalt-Catalyzed Hydroarylation of Alkynes through Chelation-Assisted C-H Bond Activation J. Am. Chem. Soc. 2010, 132, 12249-12251
23. Lim, Y.-G.; Lee, K.-H.; Koo, B. T.; Kang, J.-B. Rhodium(I)-Catalyzed ortho-Alkenylation of 2-Phenylpyridines with Alkynes Tetrahedron Lett. 2001, 42, 7609-7612
24. Lee, P.-S.; Fujita, T.; Yoshikai, N. Cobalt-Catalyzed, Room-Temperature Addition of Aromatic Imines to Alkynes via Directed C-H Bond Activation J. Am. Chem. Soc. 2011, 133, 17283-17295
25. Lim, S.-G.; Lee, J. H.; Moon, C. W.; Hong, J.-B.; Jun, C.-H. Rh(I)-Catalyzed Direct ortho-Alkenylation of Aromatic Ketimines with Alkynes and Its Application to the Synthesis of Isoquinoline Derivatives Org. Lett. 2003, 5, 2759-2761
26. Yamakawa, T.; Yoshikai, N. Cobalt-Catalyzed ortho-Alkenylation of Aromatic Aldimines via Chelation-Assisted C-H Bond Activation Tetrahedron 2013, 69, 4459-4465
27. Wakabayashi, K.; Yorimitsu, H.; Oshima, K. Cobalt-Catalyzed Tandem Radical Cyclization and Cross-Coupling Reaction: Its Application to Benzyl-Substituted Heterocycles J. Am. Chem. Soc. 2001, 123, 5374-5375
28. Yamakawa, T.; Yoshikai, N. Annulation of α,β-Unsaturated Imines and Alkynes via Cobalt-Catalyzed Olefinic C-H Activation Org. Lett. 2013, 15, 196-199
29. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Synthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C-H Activation J. Am. Chem. Soc. 2008, 130, 3645-3651
30. Parthasarathy, K.; Jeganmohan, M.; Cheng, C.-H. Rhodium-Catalyzed One-Pot Synthesis of Substituted Pyridine Derivatives from α,β-Unsaturated Ketoximes and Alkynes Org. Lett. 2008, 10, 325-328
31. Ackermann, L.; Lygin, A. V. Ruthenium-Catalyzed Direct C-H Bond Arylations of Heteroarenes Org. Lett. 2011, 13, 3332-3335
32. Ding, Z.; Yoshikai, N. Mild and Efficient C2-Alkenylation of Indoles with Alkynes Catalyzed by a Cobalt Complex Angew. Chem., Int. Ed. 2012, 51, 4698-4701
33. Schipper, D. J.; Hutchinson, M.; Fagnou, K. Rhodium(III)-Catalyzed Intermolecular Hydroarylation of Alkynes J. Am. Chem. Soc. 2010, 132, 6910-6911
34. Ding, Z.; Yoshikai, N. Cobalt-Catalyzed Addition of Azoles to Alkynes Org. Lett. 2010, 12, 4180-4183
35. Ding, Z.; Yoshikai, N. Cobalt-Catalyzed Alkenylation of Thiazoles with Alkynes via C-H Bond Functionalization Synthesis 2011, 2561-2566
36. Nakao, Y.; Kanyiva, K. S.; Oda, S.; Hiyama, T. Hydroheteroarylation of Alkynes under Mild Nickel Catalysis J. Am. Chem. Soc. 2006, 128, 8146-8147
37. Rueping, M.; Nachtsheim, B. J. A Review of New Developments in the Friedel-Crafts Alkylation - From Green Chemistry to Asymmetric Catalysis Beilstein J. Org. Chem. 2010, 6 6
38. Nakao, Y.; Kashihara, N.; Kanyiva, K. S.; Hiyama, T. Nickel-Catalyzed Hydroheteroarylation of Vinylarenes Angew. Chem., Int. Ed. 2010, 49, 4451-4454
39. Pan, S.; Ryu, N.; Shibata, T. Ir(I)-Catalyzed C-H Bond Alkylation of C2-Position of Indole with Alkenes: Selective Synthesis of Linear or Branched 2-Alkylindoles J. Am. Chem. Soc. 2012, 134, 17474-17477
40. Gao, K.; Yoshikai, N. Regioselectivity-Switchable Hydroarylation of Styrenes J. Am. Chem. Soc. 2011, 133, 400-402
41. Yang, Z.; Yu, H.; Fu, Y. Mechanistic Study on Ligand-Controlled Cobalt-Catalyzed Regioselectivity-Switchable Hydroarylation of Styrenes Chem.-Eur. J. 2013, 19, 12093-12103
42. Lee, P.-S.; Yoshikai, N. Aldimine-Directed Branched-Selective Hydroarylation of Styrenes Angew. Chem., Int. Ed. 2013, 52, 1240-1244
43. Dong, J.; Lee, P.-S.; Yoshikai, N. Cobalt-Catalyzed Branched-Selective Addition of Aromatic Ketimines to Styrenes under Room Temperature Conditions Chem. Lett. 2013, 42, 1140-1142
44. Andou, T.; Saga, Y.; Komai, H.; Matsunaga, S.; Kanai, M. Cobalt-Catalyzed C4-Selective Direct Alkylation of Pyridines Angew. Chem., Int. Ed. 2013, 52, 3213-3216
45. Kuninobu, Y.; Tatsuzaki, T.; Matsuki, T.; Takai, K. Indium-Catalyzed Construction of Polycyclic Aromatic Hydrocarbon Skeletons via Dehydration J. Org. Chem. 2011, 76, 7005-7009
46. Iwai, T.; Fujihara, T.; Tsuji, Y. The Iridium-Catalyzed Decarbonylation of Aldehydes under Mild Conditions Chem. Commun. 2008, 6215-6217
47. Gao, K.; Yoshikai, N. Cobalt-Phenanthroline Catalysts for the ortho Alkylation of Aromatic Imines under Mild Reaction Conditions Angew. Chem., Int. Ed. 2011, 50, 6888-6892
48. Ding, Z.; Yoshikai, N. C2-Alkylation of N-Pyrimidylindole with Vinylsilane via Cobalt-Catalyzed C-H Bond Activation Beilstein J. Org. Chem. 2012, 8, 1536-1542
49. I-Catalyzed ortho-Alkylation of Aromatic Ketimines or Ketones with Olefins Chem.-Eur. J. 2002, 8, 485-492
50. Ilies, L.; Chen, Q.; Zeng, X.; Nakamura, E. Cobalt-Catalyzed Chemoselective Insertion of Alkene into the Ortho C-H Bond of Benzamide J. Am. Chem. Soc. 2011, 133, 5221-5223
51. Ding, Z.; Yoshikai, N. Cobalt-Catalyzed Intramolecular Olefin Hydroarylation Leading to Dihydropyrroloindoles and Tetrahydropyridoindoles Angew. Chem., Int. Ed. 2013, 52, 8574-8578
52. Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. Annulation of Aromatic Imines via Directed C-H Bond Activation J. Org. Chem. 2005, 70, 6775-6781
53. Gao, K.; Yoshikai, N. Cobalt-Catalyzed Arylation of Aldimines via Directed C-H Bond Functionalization: Addition of 2-Arylpyridines and Self-Coupling of Aromatic Aldimines Chem. Commun. 2012, 48, 4305-4307
54. Tsai, A. S.; Tauchert, M. E.; Bergman, R. G.; Ellman, J. A. Rhodium(III)-Catalyzed Arylation of Boc-Imines via C-H Bond Functionalization J. Am. Chem. Soc. 2011, 133, 1248-1250
55. Li, Y.; Li, B.-J.; Wang, W.-H.; Huang, W. P.; Zhang, X.-S.; Chen, K.; Shi, Z.-J. Rhodium-Catalyzed Direct Addition of Aryl C-H Bonds to N-Sulfonyl Aldimines Angew. Chem., Int. Ed. 2011, 50, 2115-2119
56. III Complex for the Catalytic Generation of Nucleophilic Organometallic Species: Directed C-H Bond Activation Angew. Chem., Int. Ed. 2013, 52, 2207-2211
57. For a review on direct C-H arylation with aryl halides: Alberico, D.; Scott, M. E.; Lautens, M. Aryl-Aryl Bond Formation by Transition-Metal-Catalyzed Direct Arylation Chem. Rev. 2007, 107, 174-238
58. Gao, K.; Lee, P.-S.; Long, C.; Yoshikai, N. Cobalt-Catalyzed Ortho-Arylation of Aromatic Imines with Aryl Chlorides Org. Lett. 2012, 14, 4234-4237
59. Song, W.; Ackermann, L. Cobalt-Catalyzed Direct Arylation and Benzylation by C-H/C-O Cleavage with Sulfamates, Carbamates, and Phosphates Angew. Chem., Int. Ed. 2012, 51, 8251-8254
60. Punji, B.; Song, W.; Shevchenko, G. A.; Ackermann, L. Cobalt-Catalyzed C-H Bond Functionalizations with Aryl and Alkyl Chlorides Chem.-Eur. J. 2013, 19, 10605-10610
61. Norinder, J.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. Iron-Catalyzed Direct Arylation through Directed C-H Bond Activation J. Am. Chem. Soc. 2008, 130, 5858-5859
62. Yoshikai, N.; Asako, S.; Yamakawa, T.; Ilies, L.; Nakamura, E. Iron-Catalyzed C-H Bond Activation for the ortho-Arylation of Aryl Pyridines and Imines with Grignard Reagents Chem.-Asian J. 2011, 6, 3059-3065
63. Li, B.; Wu, Z.-H.; Gu, Y.-F.; Sun, C.-L.; Wang, B.-Q.; Shi, Z.-J. Direct Cross-Coupling of C-H Bonds with Grignard Reagents through Cobalt Catalysis Angew. Chem., Int. Ed. 2011, 50, 1109-1113
64. For a review on direct C-H alkylation with alkyl halides: Ackermann, L. Metal-Catalyzed Direct Alkylations of (Hetero)arenes via C-H Bond Cleavages with Unactivated Alkyl Halides Chem. Commun. 2010, 46, 4866-4877
65. Gao, K.; Yoshikai, N. Cobalt-Catalyzed Ortho Alkylation of Aromatic Imines with Primary and Secondary Alkyl Halides J. Am. Chem. Soc. 2013, 135, 9279-9282
66. Chen, Q.; Ilies, L.; Nakamura, E. Cobalt-Catalyzed ortho-Alkylation of Secondary Benzamide with Alkyl Chloride through Directed C-H Bond Activation J. Am. Chem. Soc. 2011, 133, 428-429
67. Chen, Q.; Ilies, L.; Yoshikai, N.; Nakamura, E. Cobalt-Catalyzed Coupling of Alkyl Grignard Reagent with Benzamide and 2-Phenylpyridine Derivatives through Directed C-H Bond Activation under Air Org. Lett. 2011, 13, 3232-3234
68. Jin, M.-Y.; Yoshikai, N. Cobalt-Xantphos-Catalyzed, LiCl-Mediated Preparation of Arylzinc Reagents from Aryl Iodides, Bromides, and Chlorides J. Org. Chem. 2011, 76, 1972-1978
69. Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Efficient Synthesis of Functionalized Organozinc Compounds by the Direct Insertion of Zinc into Organic Iodides and Bromides Angew. Chem., Int. Ed. 2006, 45, 6040-6044
70. Fillon, H.; Gosmini, C.; Perichon, J. New Chemical Synthesis of Functionalized Arylzinc Compounds from Aromatic or Thienyl Bromides under Mild Conditions Using a Simple Cobalt Catalyst and Zinc Dust J. Am. Chem. Soc. 2003, 125, 3867-3870
71. Murakami, K.; Yorimitsu, H.; Oshima, K. Cobalt-Catalyzed Arylzincation of Alkynes Org. Lett. 2009, 11, 2373-2375
72. Tan, B.-H.; Dong, J.; Yoshikai, N. Cobalt-Catalyzed Addition of Arylzinc Reagents to Alkynes to Form ortho-Alkenylarylzinc Species through 1,4-Cobalt Migration Angew. Chem., Int. Ed. 2012, 51, 9610-9614
73. Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. Rhodium-Catalyzed Hydroarylation of Alkynes with Arylboronic Acids: 1,4-Shift of Rhodium from 2-Aryl-1-alkenylrhodium to 2-Alkenylarylrhodium Intermediate J. Am. Chem. Soc. 2001, 123, 9918-9919
74. Ma, S.; Gu, Z. 1,4-Migration of Rhodium and Palladium in Catalytic Organometallic Reactions Angew. Chem., Int. Ed. 2005, 44, 7512-7517
75. Wu, B.; Yoshikai, N. Versatile Synthesis of Benzothiophenes and Benzoselenophenes by Rapid Assembly of Arylzinc Reagents, Alkynes, and Elemental Chalcogens Angew. Chem., Int. Ed. 2013, 52, 10496-10499
76. Nakamura, E.; Yoshikai, N. Low-Valent Iron-Catalyzed C-C Bond Formation-Addition, Substitution, and C-H Bond Activation J. Org. Chem. 2010, 75, 6061-6067