Cross-Couplings Using Aryl Ethers via C-O Bond Activation Enabled by Nickel Catalysts

Accounts of Chemical Research

Volumn 48, Issue 6, 2015, Pages 1717-1726

  Tobisu, Mamoru ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84934894101     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00051     Document Type: Article

References (61)

1. Nakamura, E.; Sato, K. Managing the scarcity of chemical elements Nat. Mater. 2011, 10, 158-161
2. Cross-Coupling Reactions: A Practical Guide; Miyaura, N., Ed.; Topics in Current Chemistry, Vol. 219; Wiley: Chichester, U.K., 2001.
3. For an early review, see: Fanta, P. E. The Ullmann Synthesis of Biaryls, 1945-1963 Chem. Rev. 1964, 64, 613-632
4. Tamura, M.; Kochi, J. K. Vinylation of Grignard reagents. Catalysis by iron J. Am. Chem. Soc. 1971, 93, 1487-1489
5. Kochi, J. K. Electron-transfer mechanisms for organometallic intermediates in catalytic reactions Acc. Chem. Res. 1974, 7, 351-360
6. Tamao, K.; Sumitani, K.; Kumada, M. Selective carbon-carbon bond formation by cross-coupling of Grignard reagents with organic halides. Catalysis by nickel-phosphine complexes J. Am. Chem. Soc. 1972, 94, 4374-4376
7. Corriu, R. J. P.; Masse, J. P. Activation of Grignard reagents by transition-metal complexes. A new and simple synthesis of trans -stilbenes and polyphenyls J. Chem. Soc., Chem. Commun. 1972, 144a
8. Wenkert, E.; Michelotti, E. L.; Swindell, C. S. Nickel-induced conversion of carbon-oxygen into carbon-carbon bonds. One-step transformations of enol ethers into olefins and aryl ethers into biaryls J. Am. Chem. Soc. 1979, 101, 2246-2247
9. Li, B.-J.; Yu, D.-G.; Sun, C.-L.; Shi, Z.-J. Activation of Inert Alkenyl/Aryl C-O Bond and Its Application in Cross-Coupling Reactions Chem.-Eur. J. 2011, 17, 1728-1759
10. Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-M.; Garg, N. K.; Percec, V. Nickel-Catalyzed Cross-Couplings Involving Carbon-Oxygen Bonds Chem. Rev. 2011, 111, 1346-1416
11. Tobisu, M.; Chatani, N. Catalytic Transformations Involving the Activation of sp2 Carbon-Oxygen Bonds Top. Organomet. Chem. 2013, 44, 35-53
12. Yamaguchi, J.; Muto, K.; Itami, K. Recent Progress in Nickel-Catalyzed Biaryl Coupling Eur. J. Org. Chem. 2013, 19-30
13. Cornella, J.; Zarate, C.; Martin, R. Metal-catalyzed activation of ethers via C-O bond cleavage: a new strategy for molecular diversity Chem. Soc. Rev. 2014, 43, 8081-8097
14. Leowanawat, P.; Zhang, N.; Percec, V. Nickel Catalyzed Cross-Coupling of Aryl C-O Based Electrophiles with Aryl Neopentylglycolboronates J. Org. Chem. 2012, 77, 1018-1025
15. Dankwardt, J. W. Nickel-Catalyzed Cross-Coupling of Aryl Grignard Reagents with Aromatic Alkyl Ethers: An Efficient Synthesis of Unsymmetrical Biaryls Angew. Chem., Int. Ed. 2004, 43, 2428-2432
16. Xie, L.-G.; Wang, Z.-X. Cross-Coupling of Aryl/Alkenyl Ethers with Aryl Grignard Reagents through Nickel-Catalyzed C-O Activation Chem.-Eur. J. 2011, 17, 4972-4975
17. Iglesias, M. J.; Prieto, A.; Nicasio, M. C. Kumada-Tamao-Corriu Coupling of Heteroaromatic Chlorides and Aryl Ethers Catalyzed by (IPr)Ni(allyl)Cl Org. Lett. 2012, 14, 4318-4321
18. Miyaura, N. Metal-Catalyzed Reactions of Organoboronic Acids and Esters Bull. Chem. Soc. Jpn. 2008, 81, 1535-1553
19. Tobisu, M.; Shimasaki, T.; Chatani, N. Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers with Aryl Boronic Esters Angew. Chem., Int. Ed. 2008, 47, 4866-4869
20. Shimasaki, T.; Konno, Y.; Tobisu, M.; Chatani, N. Nickel-Catalyzed Cross-Coupling Reaction of Alkenyl Methyl Ethers with Aryl Boronic Esters Org. Lett. 2009, 11, 4890-4892
21. Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. Ruthenium-Catalyzed Functionalization of Aryl Carbon-Oxygen Bonds in Aromatic Ethers with Organoboron Compounds J. Am. Chem. Soc. 2004, 126, 2706-2707
22. Ueno, S.; Mizushima, E.; Chatani, N.; Kakiuchi, F. Direct Observation of the Oxidative Addition of the Aryl Carbon-Oxygen Bond to a Ruthenium Complex and Consideration of the Relative Reactivity between Aryl Carbon-Oxygen and Aryl Carbon-Hydrogen Bonds J. Am. Chem. Soc. 2006, 128, 16516-16517
23. Zhao, Y.; Snieckus, V. Beyond Directed Ortho Metalation: Ru-Catalyzed CAr-O Activation/Cross-Coupling Reaction by Amide Chelation J. Am. Chem. Soc. 2014, 136, 11224-11227
24. Surry, D. S.; Buchwald, S. L. Biaryl Phosphane Ligands in Palladium-Catalyzed Amination Angew. Chem., Int. Ed. 2008, 47, 6338-6361
25. Hartwig, J. F. Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides Acc. Chem. Res. 2008, 41, 1534-1544
26. Tobisu, M.; Shimasaki, T.; Chatani, N. Ni0-Catalyzed Direct Amination of Anisoles Involving the Cleavage of Carbon-Oxygen Bonds Chem. Lett. 2009, 38, 710-711
27. Tobisu, M.; Yasutome, A.; Yamakawa, K.; Shimasaki, T.; Chatani, N. Ni(0)/NHC-catalyzed amination of N-heteroaryl methyl ethers through the cleavage of carbon-oxygen bonds Tetrahedron 2012, 68, 5157-5161
28. Tobisu, M.; Yamakawa, K.; Shimasaki, T.; Chatani, N. Nickel-catalyzed reductive cleavage of aryl-oxygen bonds in alkoxy- and pivaloxyarenes using hydrosilanes as a mild reducing agent Chem. Commun. 2011, 47, 2946-2948
29. álvarez-Bercedo, P.; Martin, R. Ni-Catalyzed Reduction of Inert C-O Bonds: A New Strategy for Using Aryl Ethers as Easily Removable Directing Groups J. Am. Chem. Soc. 2010, 132, 17352-17353
30. Cornella, J.; Gómez-Bengoa, E.; Martin, R. Combined Experimental and Theoretical Study on the Reductive Cleavage of Inert C-O Bonds with Silanes: Ruling Out a Classical Ni(0)/Ni(II) Catalytic Couple and Evidence for Ni(I) Intermediates J. Am. Chem. Soc. 2013, 135, 1997-2009
31. Sergeev, A. G.; Hartwig, J. F. Selective, Nickel-Catalyzed Hydrogenolysis of Aryl Ethers Science 2011, 332, 439-443
32. For a related iron-catalyzed reaction using LiAlH4, see: Ren, Y.; Yan, M.; Wang, J.; Zhang, Z. C.; Yao, K. Selective Reductive Cleavage of Inert Aryl C-O Bonds by an Iron Catalyst Angew. Chem., Int. Ed. 2013, 52, 12674-12678
33. Wang, C.; Ozaki, T.; Takita, R.; Uchiyama, M. Aryl Ether as a Negishi Coupling Partner: An Approach for Constructing C-C Bonds under Mild Conditions Chem.-Eur. J. 2012, 18, 3482-3485
34. Yoshikai, N.; Matsuda, H.; Nakamura, E. Ligand Exchange as the First Irreversible Step in the Nickel-Catalyzed Cross-Coupling Reaction of Grignard Reagents J. Am. Chem. Soc. 2008, 130, 15258-15259
35. Bryan, Z. J.; McNeil, A. J. Evidence for a preferential intramolecular oxidative addition in Ni-catalyzed cross-coupling reactions and their impact on chain-growth polymerizations Chem. Sci. 2013, 4, 1620-1624
36. Sontag, S. K.; Bilbrey, J. A.; Huddleston, N. E.; Sheppard, G. R.; Allen, W. D.; Locklin, J. π-Complexation in Nickel-Catalyzed Cross-Coupling Reactions J. Org. Chem. 2014, 79, 1836-1841
37. Tobisu, M.; Xu, T.; Shimasaki, T.; Chatani, N. Nickel-Catalyzed Suzuki-Miyaura Reaction of Aryl Fluorides J. Am. Chem. Soc. 2011, 133, 19505-19511
38. Tobisu, M.; Nakamura, K.; Chatani, N. Nickel-Catalyzed Reductive and Borylative Cleavage of Aromatic Carbon-Nitrogen Bonds in N -Aryl Amides and Carbamates J. Am. Chem. Soc. 2014, 136, 5587-5590
39. Muto, K.; Yamaguchi, J.; Itami, K. Nickel-Catalyzed C-H/C-O Coupling of Azoles with Phenol Derivatives J. Am. Chem. Soc. 2012, 134, 169-172
40. Ehle, A. R.; Zhou, Q.; Watson, M. P. Nickel(0)-Catalyzed Heck Cross-Coupling via Activation of Aryl C-OPiv Bonds Org. Lett. 2012, 14, 1202-1205
41. Correa, A.; León, T.; Martin, R. Ni-Catalyzed Carboxylation of C(sp2)- and C(sp3)-O Bonds with CO2 J. Am. Chem. Soc. 2014, 136, 1062-1069
42. Koch, E.; Takise, R.; Studer, A.; Yamaguchi, J.; Itami, K. Ni-Catalyzed α-arylation of esters and amides with phenol derivatives Chem. Commun. 2015, 51, 855-857
43. Yu, D.-G.; Li, B.-J.; Zheng, S.-F.; Guan, B.-T.; Wang, B.-Q.; Shi, Z.-J. Direct Application of Phenolic Salts to Nickel-Catalyzed Cross-Coupling Reactions with Aryl Grignard Reagents Angew. Chem., Int. Ed. 2010, 49, 4566-4570
44. Yu, D.-G.; Shi, Z.-J. Mutual Activation: Suzuki-Miyaura Coupling through Direct Cleavage of the sp2 C-O Bond of Naphtholate Angew. Chem., Int. Ed. 2011, 50, 7097-7100
45. For example, see: Martin, R.; Buchwald, S. L. Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands Acc. Chem. Res. 2008, 41, 1461-1473
46. Correa, A.; Martin, R. Ni-Catalyzed Direct Reductive Amidation via C-O Bond Cleavage J. Am. Chem. Soc. 2014, 136, 7253-7256
47. Takise, R.; Muto, K.; Yamaguchi, J.; Itami, K. Nickel-Catalyzed α-Arylation of Ketones with Phenol Derivatives Angew. Chem., Int. Ed. 2014, 53, 6791-6794
48. Kuwano, R.; Shimizu, R. An Improvement of Nickel Catalyst for Cross-Coupling Reaction of Arylboronic Acids with Aryl Carbonates by Using a Ferrocenyl Bisphosphine Ligand Chem. Lett. 2011, 40, 913-915
49. Tobisu, M.; Yasutome, A.; Kinuta, H.; Nakamura, K.; Chatani, N. 1,3-Dicyclohexylimidazol-2-ylidene as a Superior Ligand for the Nickel-Catalyzed Cross-Couplings of Aryl and Benzyl Methyl Ethers with Organoboron Reagents Org. Lett. 2014, 16, 5572-5575
50. Guan, B.-T.; Xiang, S.-K.; Wu, T.; Sun, Z.-P.; Wang, B.-Q.; Zhao, K.-Q.; Shi, Z.-J. Methylation of arenes via Ni-catalyzed aryl C-O/F activation Chem. Commun. 2008, 1437-1439
51. Leiendecker, M.; Hsiao, C.-C.; Guo, L.; Alandini, N.; Rueping, M. Metal-Catalyzed Dealkoxylative Caryl-Csp3 Cross-Coupling-Replacement of Aromatic Methoxy Groups of Aryl Ethers by Employing a Functionalized Nucleophile Angew. Chem., Int. Ed. 2014, 53, 12912-12915
52. Tobisu, M.; Takahira, T.; Ohtsuki, A.; Chatani, N. Nickel-Catalyzed Alkynylation of Anisoles via C-O Bond Cleavage Org. Lett. 2015, 17, 680-683
53. Chen, X. C.; Nishinaga, S.; Okuda, Y.; Zhao, J. J.; Xu, J.; Mori, H.; Nishihara, Y. A divergent synthesis of 3,10-dialkylpicenes Org. Chem. Front. 2015, 2, 536-541
54. Tobisu, M.; Hyodo, I.; Chatani, N. Nickel-Catalyzed Reaction of Arylzinc Reagents with N-Aromatic Heterocycles: A Straightforward Approach to C-H Bond Arylation of Electron-Deficient Heteroaromatic Compounds J. Am. Chem. Soc. 2009, 131, 12070-12071
55. For oxidative addition reactions using anisoles containing a directing group, see: Kelley, P.; Lin, S.; Edouard, G.; Day, M. W.; Agapie, T. Nickel-Mediated Hydrogenolysis of C-O Bonds of Aryl Ethers: What Is the Source of the Hydrogen? J. Am. Chem. Soc. 2012, 134, 5480-5483
56. Cornella, J.; Martin, R. Ni-Catalyzed Stereoselective Arylation of Inert C-O Bonds at Low Temperatures Org. Lett. 2013, 15, 6298-6301
57. Yoshikai, N.; Matsuda, H.; Nakamura, E. Hydroxyphosphine Ligand for Nickel-Catalyzed Cross-Coupling through Nickel/Magnesium Bimetallic Cooperation J. Am. Chem. Soc. 2009, 131, 9590-9599
58. Nakao, Y. Nickel/Lewis Acid-Catalyzed Carbocyanation of Unsaturated Compounds Bull. Chem. Soc. Jpn. 2012, 85, 731-745
59. For a leading review of catalysis by anionic ate complexes, see: Terao, J.; Kambe, N. Cross-Coupling Reaction of Alkyl Halides with Grignard Reagents Catalyzed by Ni, Pd, or Cu Complexes with π-Carbon Ligand(s) Acc. Chem. Res. 2008, 41, 1545-1554
60. Kaschube, W.; Pörschke, K.-R.; Angermund, K.; Krüger, C.; Wilke, G. Zur Lewis-Acidität von Nickel(0), X. Diorganylmagnesium-Komplexe von Nickel(0): (TMEDA)MgCH3(μ-CH3)Ni(C2H4)2 Chem. Ber. 1988, 121, 1921-1929
61. Tobisu, M.; Morioka, T.; Ohtsuki, A.; Chatani, N. Nickel-Catalyzed Reductive Cleavage of Aryl Alkyl Ethers to Arenes in Absence of External Reductant Chem. Sci. 2015, 6, 3410-3414