Carboxylate-assisted ruthenium-catalyzed alkyne annulations by C-H/Het-H bond functionalizations

Accounts of Chemical Research

Volumn 47, Issue 2, 2014, Pages 281-295

  Ackermann, Lutz ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CARBON; CARBOXYLIC ACID; NITROGEN; OXYGEN; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMISTRY; METHODOLOGY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALKYNES; CARBON; CARBOXYLIC ACIDS; CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; NITROGEN; OXIDATION-REDUCTION; OXYGEN; RUTHENIUM;

EID: 84894286870     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar3002798     Document Type: Article

References (96)

1. Modern Heterocyclic Chemistry; Alvarez-Builla, J.; Vaquero, J. J.; Barluenga, J., Eds.; Wiley-VCH: Weinheim, Germany, 2011.
2. Ackermann, L. Modern Arylation Methods; Wiley-VCH: Weinheim, Germany, 2009.
3. Mei, T.-S.; Kou, L.; Ma, S.; Engle, K. M.; Yu, J.-Q. Heterocycle Formation via Palladium-Catalyzed C-H Functionalization Synthesis 2012, 44, 1778-1791
4. Yeung, C. S.; Dong, V. M. Catalytic Dehydrogenative Cross-Coupling: Forming Carbon-Carbon Bonds by Oxidizing Two Carbon-Hydrogen Bonds Chem. Rev. 2011, 111, 1215-1292
5. 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
6. Thansandote, P.; Lautens, M. Construction of Nitrogen-Containing Heterocycles by C-H Bond Functionalization Chem.-Eur. J. 2009, 15, 5874-5883 and references cited therein
7. Hashiguchi, B. G.; Bischof, S. M.; Konnick, M. M.; Periana, R. A. Designing Catalysts for Functionalization of Unactivated C-H Bonds Based on the CH Activation Reaction Acc. Chem. Res. 2012, 45, 885-898
8. Schwarz, H. Chemistry with Methane: Concepts Rather than Recipes Angew. Chem., Int. Ed. 2011, 50, 10096-10115
9. Blanksby, S. J.; Ellison, G. B. Bond Dissociation Energies of Organic Molecules Acc. Chem. Res. 2003, 36, 255-263
10. Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Selective Intermolecular Carbon-Hydrogen Bond Activation by Synthetic Metal Complexes in Homogeneous Solution Acc. Chem. Res. 1995, 28, 154-162
11. Trost, B. M. On Inventing Reactions for Atom Economy Acc. Chem. Res. 2002, 35, 695-705
12. Chen, D. Y.-K.; Youn, S. W. C-H Activation: A Complementary Tool in the Total Synthesis of Complex Natural Products Chem.-Eur. J. 2012, 18, 9452-9474
13. McMurray, L.; O'Hara, F.; Gaunt, M. J. Recent Developments in Natural Product Synthesis Using Metal-Catalysed C-H Bond Functionalisation Chem. Soc. Rev. 2011, 40, 1885-1898
14. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions Acc. Chem. Res. 2012, 45, 814-825
15. Ackermann, L.; Vicente, R.; Kapdi, A. R. Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage Angew. Chem., Int. Ed. 2009, 48, 9792-9826
16. Ackermann, L.; Potukuchi, H. K. Regioselective Syntheses of Fully-Substituted 1,2,3-Triazoles: The CuAAC/C-H Bond Functionalization Nexus Org. Biomol. Chem. 2010, 8, 4503-4513
17. Satoh, T.; Miura, M. Catalytic Arylation and Vinylation Reactions Directed by Anionic Oxygen Functions via Cleavage of C-H and C-C Bonds Top. Organomet. Chem. 2007, 24, 61-84
18. Herrmann, P.; Bach, T. Diastereotopos-Differentiating C-H Activation Reactions at Methylene Groups Chem. Soc. Rev. 2011, 40, 2022-2038
19. Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Transition Metal-Catalyzed C-H Activation Reactions: Diastereoselectivity and Enantioselectivity Chem. Soc. Rev. 2009, 38, 3242-3272
20. Ackermann, L. Catalytic Arylations with Challenging Substrates: From Air-Stable HASPO Preligands to Indole Syntheses and C-H Bond Functionalizations Synlett 2007, 507-526 (Pubitemid 46423709)
21. September 2012, http://www.platinumgroupmetals.org/: Prices of gold, platinum, rhodium, iridium, palladium and ruthenium: $1730, $1600, $1100, $1050, $669, and $110 US per troy ounce, respectively.
22. Oi, S.; Fukita, S.; Hirata, N.; Watanuki, N.; Miyano, S.; Inoue, Y. Ruthenium Complex-Catalyzed Direct Ortho- Arylation and Alkenylation of 2-Arylpyridines with Organic Halides Org. Lett. 2001, 3, 2579-2581 (Pubitemid 33627182)
23. Lewis, L. N.; Smith, J. F. Catalytic Carbon-Carbon Bond Formation via ortho -Metalated Complexes J. Am. Chem. Soc. 1986, 108, 2728-2735
24. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Efficient Catalytic Addition of Aromatic Carbon-Hydrogen Bonds to Olefins Nature 1993, 366, 529-531 (Pubitemid 24036707)
25. Kakiuchi, F.; Chatani, N. Catalytic Methods for C-H Bond Functionalization: Application in Organic Synthesis Adv. Synth. Catal. 2003, 345, 1077-1101 (Pubitemid 37406645)
26. Kakiuchi, F.; Kochi, T. Transition-Metal-Catalyzed Carbon-Carbon Bond Formation via Carbon-Hydrogen Bond Cleavage Synthesis 2008, 3013-3039
27. An early study on amides as directing groups in palladium catalysis: Kametani, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahderon Lett 2000, 41, 2655-2658
28. Ackermann, L. Carboxylate-Assisted Transition Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope Chem. Rev. 2011, 111, 1315-1345
29. Gaunt, J. C.; Shaw, B. L. Transition Metal-Carbon Bonds: XL. Palladium(II) Complexes of [(Dimethylamino)methyl]-Ferrocene J. Organomet. Chem. 1975, 102, 511-516
30. 2 Dalton Trans. 2003, 4132-4138
31. 2 (M = Pd or Pt). A Theoretical Study Organometallics 2000, 19, 3895-3908
32. Boutadla, Y.; Davies, D. L.; MacGregor, S. A.; Poblador-Bahamonde, A. I. Mechanisms of C-H Bond Activation: Rich Synergy between Computation and Experiment Dalton Trans. 2009, 5820-5831
33. 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 (Pubitemid 43190606)
34. Lapointe, D.; Fagnou, K. Overview of the Mechanistic Work on the Concerted Metallation-Deprotonation Pathway Chem. Lett. 2010, 39, 1118-1126
35. Gorelsky, S. I.; Lapointe, D.; Fagnou, K. Analysis of the Concerted Metalation-Deprotonation Mechanism in Palladium-Catalyzed Direct Arylation Across a Broad Range of Aromatic Substrates J. Am. Chem. Soc. 2008, 130, 10848-10849
36. Ackermann, L. Air-Stable Bifunctional HASPO Preligands for Metal-Catalyzed Cross-Couplings and Direct C-H Bond Arylations Isr. J. Chem. 2010, 50, 652-663
37. Ackermann, L. Air- and Moisture-Stable Secondary Phosphine Oxides as Preligands in Catalysis Synthesis 2006, 1557-1571 (Pubitemid 43809981)
38. n]-Catalyzed Direct Arylations with Bromides as Electrophiles Synlett 2007, 2833-2836 (Pubitemid 350189833)
39. n]-catalyzed Direct Arylations Tetrahedron 2008, 64, 6115-6124
40. Ackermann, L. Phosphine Oxides as Preligands in Ruthenium-Catalyzed Arylations via C-H Bond Functionalization Using Aryl Chlorides Org. Lett. 2005, 7, 3123-3125 (Pubitemid 40992647)
41. Ackermann, L.; Althammer, A.; Born, R. Catalytic Arylation Reactions by C-H Bond Activation with Aryl Tosylates Angew. Chem., Int. Ed. 2006, 45, 2619-2622 (Pubitemid 44105775)
42. Ackermann, L.; Born, R.; Alvarez Bercedo, P. Ruthenium(IV) Alkylidenes as Precatalysts for Direct Arylations of Alkenes with Aryl Chlorides and an Application to Sequential Catalysis Angew. Chem., Int. Ed. 2007, 46, 6364-6367 (Pubitemid 47333867)
43. Ackermann, L.; Vicente, R.; Althammer, A. Assisted Ruthenium-Catalyzed C-H Bond Activation: Carboxylic Acids as Cocatalysts for Generally Applicable Direct Arylations in Apolar Solvents Org. Lett. 2008, 10, 2299-2302
44. Ackermann, L.; Vicente, R.; Potukuchi, H. K.; Pirovano, V. Mechanistic Insight into Direct Arylations with Ruthenium(II) Carboxylate Catalysts Org. Lett. 2010, 12, 5032-5035
45. Özdemir, I.; Demir, S.; Çetinkaya, B.; Gourlaouen, C.; Maseras, F.; Bruneau, C.; Dixneuf, P. H. Direct Arylation of Arene C-H Bonds by Cooperative Action of NHCarbene-Ruthenium(II) Catalyst and Carbonate via Proton Abstraction Mechanism J. Am. Chem. Soc. 2008, 130, 1156-1157 (Pubitemid 351170992)
46. Ackermann, L.; Mulzer, M. Dehydrative Direct Arylations of Arenes with Phenols via Ruthenium-Catalyzed C-H and C-OH Bond Functionalizations Org. Lett. 2008, 10, 5043-5036
47. Ackermann, L.; Pospech, J.; Potukuchi, H. K. Well-Defined Ruthenium(II) Carboxylate as Catalyst for Direct C-H/C-O Bond Arylations with Phenols in Water Org. Lett. 2012, 14, 2146-2149
48. Ackermann, L.; Vicente, R. Catalytic Direct Arylations in Polyethylene Glycol (PEG): Recyclable Palladium(0) Catalyst for C-H Bond Cleavages in the Presence of Air Org. Lett. 2009, 11, 4922-4925
49. Arockiam, P. B.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. H. C-H Bond Functionalization in Water Catalyzed by Carboxylato Ruthenium(II) Systems Angew. Chem., Int. Ed. 2010, 49, 6629-6632
50. Ouellet, S. G.; Roy, A.; Molinaro, C.; Angelaud, R.; Marcoux, J.-F.; O'Shea, P. D.; Davies, I. W. Preparative Scale Synthesis of the Biaryl Core of Anacetrapib via a Ruthenium-Catalyzed Direct Arylation Reaction: Unexpected Effect of Solvent Impurity on the Arylation Reaction J. Org. Chem. 2011, 76, 1436-1439
51. Ackermann, L.; Lygin, A. V. Ruthenium-Catalyzed Direct C-H Bond Arylations of Heteroarenes Org. Lett. 2011, 13, 3332-3335
52. Ackermann, L.; Diers, E.; Manvar, A. Ruthenium-Catalyzed C-H Bond Arylations of Arenes Bearing Removable Directing Groups via Six-Membered Ruthenacycles Org. Lett. 2012, 14, 1154-1157
53. 3 C-H Bond Arylation of Benzylic Amines Using Aryl Halides Org. Lett. 2012, 14, 3792-3795
54. Ackermann, L.; Novák, P. Regioselective Ruthenium-Catalyzed Direct Benzylations of Arenes through C-H Bond Cleavages Org. Lett. 2009, 11, 4966-4969
55. Ackermann, L.; Novák, P.; Vicente, R.; Hofmann, N. Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage Angew. Chem., Int. Ed. 2009, 48, 6045-6048
56. Ackermann, L. Metal-Catalyzed Direct Alkylations of (Hetero)Arenes via C-H Bond Cleavages with Unactivated Alkyl Halides Chem. Commun. 2010, 46, 4866-4877
57. Ackermann, L.; Hofmann, N.; Vicente, R. Carboxylate-Assisted Ruthenium-Catalyzed Direct Alkylations of Ketimines Org. Lett. 2011, 13, 1875-1877
58. Ackermann, L.; Novák, P.; Vicente, R.; Pirovano, V.; Potukuchi, H. K. Ruthenium-Catalyzed C-H Bond Functionalizations of 1,2,3-Triazol-4-yl- Substituted Arenes: Dehydrogenative Couplings versus Direct Arylations Synthesis 2010, 2245-2253
59. 2 J. Am. Chem. Soc. 2001, 123, 337-338 (Pubitemid 32062175)
60. Ueyama, T.; Mochida, S.; Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M. Ruthenium-Catalyzed Oxidative Vinylation of Heteroarene Carboxylic Acids with Alkenes via Regioselective C-H Bond Cleavage Org. Lett. 2011, 13, 706-708
61. Song, G.; Wang, F.; Li, X. C-C, C-O and C-N Bond Formation via Rhodium(III)-Catalyzed Oxidative C-H Activation Chem. Soc. Rev. 2012, 41, 3651-3678
62. Zhu, C.; Wang, R.; Falck, J. R. Amide-Directed Tandem C-C/C-N Bond Formation through C-H Activation Chem.-Asian J. 2012, 7, 1502-1514
63. Fujiwara, Y.; Noritani, I.; Danno, S.; Asano, R.; Teranishi, S. Aromatic Substitution of Olefins. VI. Arylation of Olefins with Palladium(II) Acetate J. Am. Chem. Soc. 1969, 91, 7166-7169
64. Hong, P.; Yamazaki, H. Reactions of Ethylene and Benzenes Catalyzed by Rhodium Carbonyls under Carbon Monoxide. The Formation of Styrenes and 3-Pentanone Chem. Lett. 1979, 1335-1336
65. For recent progress with rhodium catalysts, see: Satoh, T.; Miura, M. Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis Chem.-Eur. J. 2010, 16, 11212-11222
66. Recent advances with palladium catalysts: Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions Acc. Chem. Res. 2012, 45, 788-802
67. A notable nickel-catalyzed example: Shiota, H.; Ano, Y.; Aihara, Y.; Fukumoto, Y.; Chatani, N. Nickel-Catalyzed Chelation-Assisted Transformations Involving ortho C-H Bond Activation: Regioselective Oxidative Cycloaddition of Aromatic Amides to Alkynes J. Am. Chem. Soc. 2011, 133, 14952-14955
68. Ackermann, L.; Lygin, A. V.; Hofmann, N. Ruthenium-Catalyzed Oxidative Annulation via C-H/N-H Bond Cleavages Angew. Chem., Int. Ed. 2011, 50, 6379-6382
69. Deponti, M.; Kozhushkov, S. I.; Yufit, D. S.; Ackermann, L. Ruthenium-Catalyzed C-H/O-H and C-H/N-H Bond Functionalizations: Oxidative Annulations of Cyclopropyl-Substituted Alkynes Org. Biomol. Chem. 2013, 11, 142-148
70. a Values of C-H Bonds in Aromatic Heterocyclic Compounds in DMSO? Tetrahedron 2007, 63, 1568-1576 (Pubitemid 46074114)
71. Li, B.; Feng, H.; Wang, N.; Ma, J.; Song, H.; Xu, S.; Wang, B. Ruthenium-Catalyzed Oxidative Coupling/Cyclization of Isoquinolones with Alkynes through C-H/N-H Activation: Mechanism Study and Synthesis of Dibenzo[ a, g ]quinolizin-8-one Derivatives Chem.-Eur. J. 2012, 18, 12873-12879
72. Li, B.; Roisnel, T.; Darcel, C.; Dixneuf, P. H. Cyclometallation of Arylimines and Nitrogen-Containing Heterocycles via Room-Temperature C-H Bond Activation with Arene Ruthenium(II) Acetate Complexes Dalton Trans. 2012, 41, 10934-10937
73. Ackermann, L.; Lygin, A. V.; Hofmann, N. Ruthenium-Catalyzed Oxidative Synthesis of 2-Pyridones through C-H/N-H Bond Functionalizations Org. Lett. 2011, 13, 3278-3281
74. Su, Y.; Zhao, M.; Han, K.; Song, G.; Li, X. Synthesis of 2-Pyridones and Iminoesters via Rh(III)-Catalyzed Oxidative Coupling between Acrylamides and Alkynes Org. Lett. 2010, 12, 5462-5465
75. Ackermann, L.; Lygin, A. V. Cationic Ruthenium(II) Catalysts for Oxidative C-H/N-H Bond Functionalizations of Anilines with Removable Directing Group: Synthesis of Indoles in Water Org. Lett. 2012, 14, 764-767
76. See also: Wang, L.; Ackermann, L. Versatile Pyrrole Synthesis through Ruthenium(II)-Catalyzed Alkene C-H Bond Functionalization on Enamines Org. Lett. 2013, 15, 176-179
77. Butler, R. N.; Coyne, A. G. Water: Nature's Reaction Enforcer-Comparative Effects for Organic Synthesis "In-Water" and "On-Water" Chem. Rev. 2010, 110, 6302-6337
78. Ackermann, L.; Wang, L.; Lygin, A. V. Ruthenium-Catalyzed Aerobic Oxidative Coupling of Alkynes with 2-Aryl-Substituted Pyrroles Chem. Sci. 2012, 3, 177-180
79. Ackermann, L.; Pospech, J. Ruthenium-Catalyzed Oxidative C-H Bond Alkenylations in Water: Expedient Synthesis of Annulated Lactones Org. Lett. 2011, 13, 4153-4155
80. A review: Satoh, T.; Miura, M. Transition-Metal-Catalyzed Regioselective Arylation and Vinylation of Carboxylic Acids Synthesis 2010, 3395-3409
81. Kozhushkov, S. I.; Ackermann, L. Chem. Sci. 2013, 10.1039/C2SC21524A
82. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Ruthenium(II)-Catalyzed C-H Bond Activation and Functionalization Chem. Rev. 2012, 112, 5879-5918
83. Graczyk, K.; Ma, W.; Ackermann, L. Oxidative Alkenylation of Aromatic Esters by Ruthenium-Catalyzed Twofold C-H Bond Cleavages Org. Lett. 2012, 14, 4110-4113
84. Related ruthenium(II)-catalyzed alkenylations by aza-Michael addition: Ackermann, L.; Wang, L.; Wolfram, R.; Lygin, A. V. Ruthenium-Catalyzed Oxidative C-H Alkenylations of Anilides and Benzamides in Water Org. Lett. 2012, 14, 728-731
85. Ackermann, L.; Pospech, J.; Graczyk, K.; Rauch, K. Versatile Synthesis of Isocoumarins and α-Pyrones by Ruthenium-Catalyzed Oxidative C-H/O-H Bond Cleavages Org. Lett. 2012, 14, 930-933
86. Chinnagolla, R. K.; Jeganmohan, M. Regioselective Synthesis of Isocoumarins by Ruthenium-Catalyzed Aerobic Oxidative Cyclization of Aromatic Acids with Alkynes Chem. Commun. 2012, 48, 2030-2032
87. Thirunavukkarasu, V. S.; Donati, M.; Ackermann, L. Hydroxyl-Directed Ruthenium-Catalyzed C-H Bond Functionalization: Versatile Access to Fluorescent Pyrans Org. Lett. 2012, 14, 3416-3419
88. 2)-H Bond Hydroxylation: Site-Selective C-O Bond Formation on Benzamides Org. Lett. 2012, 14, 4210-4213
89. 8 as the oxidant, see: Yang, Y.; Lin, Y.; Rao, Y. Ruthenium(II)-Catalyzed Synthesis of Hydroxylated Arenes with Ester as an Effective Directing Group Org. Lett. 2012, 14, 2874-2877
90. Patureau, F. W.; Glorius, F. Oxidizing Directing Groups Enable Efficient and Innovative C-H Activation Reactions Angew. Chem., Int. Ed. 2011, 50, 1977-1979
91. Ackermann, L.; Fenner, S. Ruthenium-Catalyzed C-H/N-O Bond Functionalization: Green Isoquinolone Syntheses in Water Org. Lett. 2011, 13, 6548-6551
92. Li, B.; Feng, H.; Xu, S.; Wang, B. Ruthenium-Catalyzed Isoquinolone Synthesis through C-H Activation Using an Oxidizing Directing Group Chem.-Eur. J. 2011, 17, 12573-12577
93. See also: Parthasarathy, K.; Senthilkumar, N.; Jayakumar, J.; Cheng, C.-H. Ru(II)-Catalyzed C-H Bond Activation for the Synthesis of Substituted Isoquinolinium Salts from Benzaldehydes, Amines, and Alkynes Org. Lett. 2012, 14, 3478-3481
94. Kornhaaß, C.; Li, J.; Ackermann, L. Cationic Ruthenium Catalysts for Alkyne Annulations with Oximes by C-H/N-O Functionalizations J. Org. Chem. 2012, 77, 9190-9198
95. Chinnagolla, R. K.; Pimparkar, S.; Jeganmohan, M. Ruthenium-Catalyzed Highly Regioselective Cyclization of Ketoximes with Alkynes by C-H Bond Activation: A Practical Route to Synthesize Substituted Isoquinolines Org. Lett. 2012, 14, 3032-3035
96. Reaction sequences comprising ortho -selective hydroarylation and subsequent nucleophilic attack on aromatic ketones: Chinnagolla, R. K.; Jeganmohan, M. Ruthenium-Catalyzed Regioselective Cyclization of Aromatic Ketones with Alkynes: An Efficient Route to Indenols and Benzofulvenes Eur. J. Org. Chem. 2012, 417-423