Ipso- borylation of aryl ethers via Ni-Catalyzed C-OMe Cleavage

Journal of the American Chemical Society

Volumn 137, Issue 21, 2015, Pages 6754-6757

  Zarate, Cayetana ^a   Manzano, Rubén ^a   Martin, Ruben ^a,b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ETHERS;

ARYL ETHER; BORON REAGENTS; BORYLATION; SITE SELECTIVITY;

NICKEL;

BORON; ETHER DERIVATIVE;

ARTICLE; CATALYSIS; CONTROLLED STUDY; COVALENT BOND; HALOGENATION; ONE POT SYNTHESIS; REACTION OPTIMIZATION; STOICHIOMETRY;

EID: 84930680277     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b03955     Document Type: Article

References (68)

1. Tehetena, M.; Garg, N. K. Org. Process Res. Dev. 2013, 17, 129
2. Yamaguchi, J.; Muto, K.; Itami, K. Eur. J. Org. Chem. 2013, 19
3. Correa, A.; Cornella, J.; Martin, R. Angew. Chem., Int. Ed. 2013, 52, 1878
4. Tobisu, M.; Chatani, N. Top. Organomet. Chem. 2013, 44, 35
5. Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev. 2011, 111, 1346
6. Li, B.-J.; Yu, D.-G.; Sun, C.-L.; Shi, Z.-J. Chem. - Eur. J. 2011, 17, 1728
7. Yu, D.-G.; Li, B.-J.; Shi, Z.-J. Acc. Chem. Res. 2010, 43, 1486
8. Cornella, J.; Zarate, C.; Martin, R. Chem. Soc. Rev. 2014, 43, 8081
9. Tobisu, M.; Shimasaki, T.; Chatani, N. Chem. Lett. 2009, 38, 710
10. Tobisu, M.; Yasutome, A.; Yamakawa, K.; Shimasaki, T.; Chatani, N. Tetrahedron 2012, 68, 5157
11. Hall, D. G. Boronic Acids; Wiley-VCH: Weinheim, Germany, 2005.
12. Suzuki, A.; Brown, H. C. Organic Synthesis via Boranes; Aldrich: Milwaukee, WI, 2003.
13. Uematsu, R.; Yamamoto, E.; Maeda, S.; Ito, H. J. Am. Chem. Soc. 2015, 137, 4090
14. Molander, G. A.; Trice, S. L. J.; Dreher, S. D. J. Am. Chem. Soc. 2010, 132, 17701
15. Moldoveanu, C.; Wilson, D. A.; Wilson, C. J.; Leowanawat, P.; Resmerita, A.-M.; Liu, C.; Rosen, B. M.; Percec, V. J. Org. Chem. 2010, 75, 5438
16. Zhu, W.; Ma, D. Org. Lett. 2005, 8, 261
17. Ishiyama, T.; Miyaura, N. Chem. Rec. 2004, 3, 271 and citations therein
18. Ros, A.; Fernández, R.; Lassaletta, J. M. Chem. Soc. Rev. 2014, 43, 3229
19. Hartwig, J. F. Chem. Soc. Rev. 2011, 40, 1992
20. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890
21. Miyaura, N. Bull. Chem. Soc. Jpn. 2008, 81, 1535
22. Tobisu, M.; Kinuta, H.; Kita, Y.; Rémond, E.; Chatani, N. J. Am. Chem. Soc. 2012, 134, 115
23. Tobisu, M.; Nakamura, K.; Chatani, N. J. Am. Chem. Soc. 2014, 136, 5587
24. For synthetic pathways based on transmetalation events from RLi or RMgBr: Brown, H. C.; Cole, T. E. Organometallics 1983, 2, 1316
25. Snieckus, V. Chem. Rev. 1990, 90, 879
26. Hartung, C. G.; Snieckus, V. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 330-367.
27. Taylor, R. Electrophilic Aromatic Substitutions; Wiley-VCH: Weinheim, Germany, 1990.
28. Niu, L.; Yang, H.; Wang, R.; Fu, H. Org. Lett. 2012, 14, 2618
29. Del Grosso, A.; Pritchard, R. G.; Muryn, C. A.; Ingleson, M. J. Organometallics 2010, 29, 241
30. Muetterties, E. L. J. Am. Chem. Soc. 1960, 82, 4163
31. Kinuta, H.; Hasegawa, J.; Tobisu, M.; Chatani, N. Chem. Lett. 2015, 44, 366
32. Huang, K.; Yu, D.-G.; Zheng, S.-F.; Wu, Z.-H.; Shi, Z.-J. Chem. - Eur. J. 2011, 17, 786
33. Chow, W. K.; So, C. M.; Lau, C. P.; Kwong, F. Y. Chem. - Eur. J. 2011, 17, 6913
34. Wilson, D. A.; Wilson, C. J.; Moldoveanu, C.; Resmerita, A.-M.; Corcoran, P.; Hoang, L. M.; Rosen, B. M.; Percec, V. J. Am. Chem. Soc. 2010, 132, 1800
35. Klumpp, G. W. Reactivity in Organic Chemistry; Wiley: New York, 1982; pp 227-378.
36. Zarate, C.; Martin, R. J. Am. Chem. Soc. 2014, 136, 2236
37. Liu, Y.; Cornella, J.; Martin, R. J. Am. Chem. Soc. 2014, 136, 11212
38. Moragas, T.; Cornella, J.; Martin, R. J. Am. Chem. Soc. 2014, 136, 17702
39. Correa, A.; Martin, R. J. Am. Chem. Soc. 2014, 136, 7253
40. Cornella, J.; Martin, R. Org. Lett. 2013, 15, 6298
41. Cornella, J.; Gómez-Bengoa, E.; Martin, R. J. Am. Chem. Soc. 2013, 135, 1997
42. Barbero, N.; Martin, R. Org. Lett. 2012, 14, 796
43. álvarez-Bercedo, R.; Martin, R. J. Am. Chem. Soc. 2010, 132, 17352
44. While this paper was in preparation, an elegant Rh-catalyzed C-B bond formation of activated aryl ethers decorated with an O-pyridyl group appeared: Kinuta, H.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2015, 137, 1593
45. The lack of reactivity of C-OMe bonds is clearly illustrated in a recent Ni-catalyzed C-H borylation in which 7% of C-OMe borylation was observed: Furukawa, T.; Tobisu, M.; Chatani, N. Chem. Commun. 2015, 51, 6508
46. Diederich, F.; de Meijere, A., Eds. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 2004.
47. For an elegant structural work on the use of additives for activating B-B bonds: Pietsch, S.; Neeve, E. C.; Apperley, D. C.; Bertermann, R.; Mo, F.; Qiu, D.; Cheung, M. S.; Dang, Li; Wang, J.; Radius, U.; Lin, Z.; Kleeberg, C.; Marder, T. B. Chem. - Eur. J. 2015, 21, 7082
48. Tobisu, M.; Yasutome, A.; Kinuta, H.; Nakamura, K.; Chatani, N. Org. Lett. 2014, 16, 5572
49. Tobisu, M.; Morioka, T.; Ohtsuki, A.; Chatani, N. Chem. Sci. 2015, 6, 3410
50. Fürstner, A.; Majima, K.; Martin, R.; Krause, H.; Kattnig, E.; Goddard, R.; Lehmann, W. J. Am. Chem. Soc. 2008, 130, 1992
51. Ref 13f.
52. Matthew, S. C.; Glasspoole, B. W.; Eisenberger, P.; Crudden, C. M. J. Am. Chem. Soc. 2014, 136, 5828
53. Nave, S.; Sonawane, R. P.; Elford, T. G.; Aggarwal, V. K. J. Am. Chem. Soc. 2010, 132, 17096
54. Atack, T. C.; Lecker, R. M.; Cook, S. P. J. Am. Chem. Soc. 2014, 136, 9521
55. Bose, S. K.; Fucke, K.; Liu, L.; Steel, P. G.; Marder, T. B. Angew. Chem., Int. Ed. 2014, 53, 1799
56. Dudnik, A. S.; Fu, G. C. J. Am. Chem. Soc. 2012, 134, 10693
57. Joshi-Pangu, A.; Ma, X.; Diane, M.; Iqbal, S.; Kribs, R. J.; Huang, R.; Wang, C.-Y.; Biscoe, M. R. J. Org. Chem. 2012, 77, 6629
58. Racemization occurred with enantioenriched 1n, an observation that is tentatively attributed to bimolecular-type mechanisms. For a related scenario, see: Yonova, I. M.; Johnson, A. G.; Osborne, C. A.; Moore, C. E.; Morrissette, N. S.; Jarvo, E. R. Angew. Chem., Int. Ed. 2014, 53, 2422
59. Wisniewska, H. M.; Swift, E. C.; Jarvo, E. R. J. Am. Chem. Soc. 2013, 135, 9083
60. Zhou, Q.; Srinivas, H. D.; Dasgupta, S.; Watson, M. P. J. Am. Chem. Soc. 2013, 135, 3307
61. Taylor, B. L.; Harris, M. R.; Jarvo, E. R. Angew. Chem., Int. Ed. 2012, 51, 7790
62. Yu, D.-G.; Shi, Z.-J. Angew. Chem., Int. Ed. 2011, 50, 7097
63. Yu, D. G.; Li, B. J.; Zheng, S. F.; Guan, B. T.; Wang, B. Q.; Shi, Z. J. Angew. Chem., Int. Ed. 2010, 49, 4566
64. Tobisu, M.; Shimasaki, T.; Chatani, N. Angew. Chem., Int. Ed. 2008, 47, 4866 and citations therein
65. Bauer, D. J.; Krueger, C. Inorg. Chem. 1977, 16, 884
66. Shi, H.; Babinski, D. J.; Ritter, T. J. Am. Chem. Soc. 2015, 137, 3775
67. Murphy, J. M.; Liao, X.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 15434 and citations therein
68. Bew, S. P. In Comprehensive Organic Functional Group Transformations II; Katritzky, A. R.; Taylor, R. J. K., Eds.; Elsevier: Oxford, 2005.