Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C-O Bond-Cleaving Alkylation: Prevention of Undesired β-Hydride Elimination

Angewandte Chemie - International Edition

Volumn 55, Issue 20, 2016, Pages 6093-6098

  Liu, Xiangqian ^a   Hsiao, Chien Chi ^a   Kalvet, Indrek ^a   Leiendecker, Matthias ^a   Guo, Lin ^a   Schoenebeck, Franziska ^a   Rueping, Magnus ^a,b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Saudi Arabia)

Author keywords

C C cross coupling; C O bond activation; cross coupling; nickel; trialkylaluminum

Indexed keywords

ALKYLATION; CATALYSIS; CHEMICAL ACTIVATION; CHEMICAL REACTIONS; ETHERS; HYDRIDES;

ARYL METHYL ETHER; BOND ACTIVATION; C-C CROSS-COUPLINGS; CROSS-COUPLINGS; HYDRIDE ELIMINATION; NATURALLY OCCURRING; SYNTHETIC STRATEGIES; TRIALKYLALUMINUM;

NICKEL;

EID: 84981765530     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201510497     Document Type: Article

References (95)

1. E.-I. Negishi, Angew. Chem. Int. Ed. 2011, 50, 6738-6764;
2. Angew. Chem. 2011, 123, 6870-6897;
3. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. Int. Ed. 2005, 44, 4442-4489;
4. Angew. Chem. 2005, 117, 4516-4563;
5. J. P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651-2710;
6. J. Magano, J. R. Dunetz, Chem. Rev. 2011, 111, 2177-2250;
7. Metal-Catalyzed Cross-Coupling Reactions (Eds.:, A. de Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004;
8. E.-i. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis Wiley-Interscience, New York, 2002;
9. Metal-Catalyzed Cross-Coupling Reactions and More (Eds.:, A. de Meijere, S. Bräse, M. Oestreich,), Wiley-VCH, Weinheim, 2014;
10. New Trends in Cross-Coupling Theory and Applications (Ed.:, T. J. Colacot,), RSC Catalysis Series, London, 2015.
11. J. Cornella, C. Zarate, R. Martin, Chem. Soc. Rev. 2014, 43, 8081-8097;
12. B.-J. Li, D.-G. Yu, C.-L. Sun, Z.-J. Shi, Chem. Eur. J. 2011, 17, 1728-1759;
13. T. Mesganaw, N. K. Garg, Org. Process Res. Dev. 2013, 17, 29-39;
14. S. I. Kozhushkov, H. K. Potukuchiw, L. Ackermann, Catal. Sci. Technol. 2013, 3, 562-571;
15. W.-N. Li, Z.-L. Wang, RSC Adv. 2013, 3, 25565-25575;
16. M. Tobisu, N. Chatani, Top. Organomet. Chem. 2013, 44, 35-54;
17. D.-G. Yu, B.-J. Li, Z.-J. Shi, Acc. Chem. Res. 2010, 43, 1486-1495; for reviews on Ni-catalyzed C-O bond activation, see:
18. B. M. Rosen, K. W. Quasdorf, D. A. Wilson, N. Zhang, A.-M. Resmerita, N. K. Garg, V. Percec, Chem. Rev. 2011, 111, 1346-1416;
19. M. Tobisu, N. Chatani, Acc. Chem. Res. 2015, 48, 1717-1726.
20. G. W. Klumpp, Reactivity in Organic Chemistry, Wiley, New York, 1982;
21. G. A. Olah, J. A. Olah, T. Ohyama, J. Am. Chem. Soc. 1984, 106, 5284-5290.
22. J. Clayden, Organolithiums: Selectivity for Synthesis, Wiley-VCH, Weinheim, 2002;
23. V. Snieckus, Chem. Rev. 1990, 90, 879-933.
24. R. Taylor, Electrophilic Aromatic Substitution, Wiley, New York, 1995.
25. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483;
26. J. K. Stille, Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524;
27. Angew. Chem. 1986, 98, 504-519;
28. C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217-6254;
29. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. Int. Ed. 2009, 48, 9792-9826;
30. Angew. Chem. 2009, 121, 9976-10011;
31. A. Brennführer, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2009, 48, 4114-4133;
32. Angew. Chem. 2009, 121, 4176-4196;
33. R. Jana, T. P. Pathak, M. S. Sigman, Chem. Rev. 2011, 111, 1417-1492;
34. I. A. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890-931.
35. Modern Organonickel Chemistry (Ed.:, Y. Tamaru,), Wiley-VCH, Weinheim, 2005;
36. V. B. Phapale, D. J. Cárdenas, Chem. Soc. Rev. 2009, 38, 1598-1607;
37. J. Yamaguchi, K. Muto, K. Itami, Eur. J. Org. Chem. 2013, 19-30;
38. F.-S. Han, Chem. Soc. Rev. 2013, 42, 5270-5298;
39. S. Z. Tasker, E. A. Standley, T. F. Jamison, Nature 2014, 509, 299-309.
40. E. Wenkert, E. L. Michelotti, C. S. Swindell, J. Am. Chem. Soc. 1979, 101, 2246-2247.
41. J. W. Dankwardt, Angew. Chem. Int. Ed. 2004, 43, 2428-2432;
42. Angew. Chem. 2004, 116, 2482-2486;
43. M. Tobisu, T. Shimasaki, N. Chatani, Angew. Chem. Int. Ed. 2008, 47, 4866-4869;
44. Angew. Chem. 2008, 120, 4944-4947;
45. C. Wang, T. Ozaki, R. Takita, M. Uchiyama, Chem. Eur. J. 2012, 18, 3482-3485;
46. M. Tobisu, A. Yasutome, H. Kinuta, K. Nakamura, N. Chatani, Org. Lett. 2014, 16, 5572-5575.
47. B.-T. Guan, S.-K. Xiang, T. Wu, Z.-P. Sun, B.-Q. Wang, K.-Q. Zhao, Z.-J. Shi, Chem. Commun. 2008, 1437-1439;
48. T. Morioka, A. Nishizawa, K. Nakamura, M. Tobisu, N. Chatani, Chem. Lett. 2015, 44, 1729-1731.
49. M. Tobisu, T. Takahira, A. Ohtsuki, N. Chatani, Org. Lett. 2015, 17, 680-683.
50. M. Tobisu, T. Shimasaki, N. Chatani, Chem. Lett. 2009, 38, 710-711;
51. M. Tobisu, A. Yasutome, K. Yamakawa, T. Shimasaki, N. Chatani, Tetrahedron 2012, 68, 5157-5161.
52. C. Zarate, R. Manzano, R. Martin, J. Am. Chem. Soc. 2015, 137, 6754-6757.
53. P. Alvarez-Bercedo, R. Martin, J. Am. Chem. Soc. 2010, 132, 17352-17353;
54. A. G. Sergeev, J. F. Hartwig, Science 2011, 332, 439-443;
55. M. Tobisu, K. Yamakawa, T. Shimasaki, N. Chatani, Chem. Commun. 2011, 47, 2946-2948;
56. M. Tobisu, T. Morioka, A. Ohtsuki, N. Chatani, Chem. Sci. 2015, 6, 3410-3414.
57. M. Leiendecker, C. C. Hsiao, L. Guo, N. Alandini, M. Rueping, Angew. Chem. Int. Ed. 2014, 53, 12912-12915;
58. Angew. Chem. 2014, 126, 13126-13129;
59. L. Guo, M. Leiendecker, C.-C. Hsiao, C. Baumann, M. Rueping, Chem. Commun. 2015, 51, 1937-1940;
60. M. Leiendecker, A. Chatupheeraphat, M. Rueping, Org. Chem. Front. 2015, 2, 350-353.
61. "Nickel-catalyzed cross-coupling reactions":, A. Adhikary, H. Guan, in Pincer and Pincer-Type Complexes (Eds.:, K. J. Szabo, O. Wendt,), Wiley, Hoboken, 2014, pp. 117-147;
62. 3-carbon centers. Nickel Catalysts":, T. Iwasaki, N. Kambe, in Comprehensive Organic Synthesis, Vol. 3, 2 nd ed., (Eds.: P. Knochel, G. A. Molander,), Elsevier, Oxford, 2014, pp. 358-371;
63. 2 carbon centers. Nickel-Catalyzed Coupling Reactions":, G. Manolikakes, in Comprehensive Organic Synthesis, Vol. 3, 2 nd ed., (Eds.: P. Knochel, G. A. Molander,), Elsevier, Oxford, 2014, pp. 430-442.
64. 2)-O bonds is limited to methylation. For the Ni-catalyzed coupling of methoxynaphthalene with adamantyl and cyclopropyl Grignard reagents, see:
65. 11MgBr.
66. K. W. Quasdorf, A. Antoft-Finch, P. Liu, A. L. Silberstein, A. Komaromi, T. Blackburn, S. D. Ramgren, K. N. Houk, V. Snieckus, N. K. Garg, J. Am. Chem. Soc. 2011, 133, 6352-6363;
67. Z. Li, S. L. Zhang, Y. Fu, Q. X. Guo, L. Liu, J. Am. Chem. Soc. 2009, 131, 8815-8823;
68. A. B. Dürr, G. Yin, I. Kalvet, F. Napoly, F. Schoenebeck, Chem. Sci. 2016, 7, 1076-1081.
69. D.-G. Yu, Z.-J. Shi, Angew. Chem. Int. Ed. 2011, 50, 7097-7100;
70. Angew. Chem. 2011, 123, 7235-7238;
71. J. Cornella, R. Martin, Org. Lett. 2013, 15, 6298-6301.
72. M. Schlosser, Organometallics in Synthesis: A Manual, 2 nd ed., Wiley, The Atrium, 2002.
73. P. Knochel, T. Blümke, K. Groll, Y. H. Chen, Top. Organomet. Chem. 2013, 41, 173-186;
74. P. von Zezschwitz, Top. Organomet. Chem. 2013, 41, 245-276; for selected examples of cross-couplings with organoaluminum reagents, see:
75. R. Shang, L. Ilies, E. Nakamura, J. Am. Chem. Soc. 2015, 137, 7660-7663;
76. K. Groll, T. Blümke, A. Unsinn, D. Haas, P. Knochel, Angew. Chem. Int. Ed. 2012, 51, 11157-11161;
77. Angew. Chem. 2012, 124, 11319-11323;
78. N. A. Bumagin, A. B. Ponomaryov, I. P. Beletskaya, J. Organomet. Chem. 1985, 291, 129-132;
79. S. Kawamura, K. Ishizuka, H. Takaya, M. Nakamura, Chem. Commun. 2010, 46, 6054-6056;
80. H. Gao, P. Knochel, Synlett 2009, 1321-1325;
81. W.-T. Shu, S. Zhou, H.-M. Gau, Synthesis 2009, 4075-4081;
82. D. B. Biradar, H.-M. Gau, Chem. Commun. 2011, 47, 10467-10469;
83. H. Naka, M. Uchiyama, Y. Matsumoto, A. E. H. Wheatley, M. McPartlin, J. V. Morey, Y. Kondo, J. Am. Chem. Soc. 2007, 129, 1921-1930;
84. H. Schumann, J. Kaufmann, H.-G. Schmalz, A. Böttcher, B. Gotov, Synlett 2003, 1783-1788.
85. K. Muto, J. Yamaguchi, K. Itami, J. Am. Chem. Soc. 2012, 134, 169-172.
86. Gaussian 09, Revision D.01, see the Supporting Information for the full reference; for the appropriateness of the chosen computational model, see:
87. T. Sperger, I. A. Sanhueza, I. Kalvet, F. Schoenebeck, Chem. Rev. 2015, 115, 9532-9586;
88. R. R. A. Freund, H. Görls, J. Langer, Dalton Trans. 2014, 43, 13988-14000;
89. X. Hong, Y. Liang, K. N. Houk, J. Am. Chem. Soc. 2014, 136, 2017-2025;
90. Q. Lu, H. Yu, Y. Fu, J. Am. Chem. Soc. 2014, 136, 8252-8260;
91. H. Xu, K. Muto, J. Yamaguchi, C. Zhao, K. Itami, D. G. Musaev, J. Am. Chem. Soc. 2014, 136, 14834-14844.
92. -1).
93. -1) in 1) the "LLHT mechanism" with a Ni-H interaction cis to the naphthyl residue and direct ArH formation or 2) via trans Ni-H interactions leading to a Ni-H intermediate. For a report on the LLHT mechanism, see:, J. Guihaumé, S. Halbert, O. Eisenstein, R. N. Perutz, Organometallics 2012, 31, 1300-1314.
94. J. Cornella, E. Gómez-Bengoa, R. Martin, J. Am. Chem. Soc. 2013, 135, 1997-2009.
95. G. Yin, I. Kalvet, U. Englert, F. Schoenebeck, J. Am. Chem. Soc. 2015, 137, 4164-4172.