Palladium-Catalyzed ipso-Borylation of Aryl Sulfides with Diborons

Organic Letters

Volumn 18, Issue 12, 2016, Pages 2966-2969

  Bhanuchandra, M ^a   Baralle, Alexandre ^a   Otsuka, Shinya ^a   Nogi, Keisuke ^a   Yorimitsu, Hideki ^a   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84975257576     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.6b01305     Document Type: Article

References (70)

1. Suzuki, A.; Brown, H. C. Organic Syntheses Via Boranes; Aldrich Chemical Company: Milwaukee, 2003; Vol. 3.
2. Miyaura, N. In Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
3. Boronic Acids, 2 nd ed.; Hall, D. G., Ed.; Wiley-VCH: Weinheim, Germany, 2011.
4. Applied Cross-Coupling Reactions; Nishihara, Y., Ed.; Springer: Heidelberg, 2013.
5. Synthesis and Application of Organoboron Compounds; Fernández, E., Whiting, A., Eds.; Springer: Heidelberg, 2015.
6. Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508 10.1021/jo00128a024
7. Ishiyama, T.; Itoh, Y.; Kitano, T.; Miyaura, N. Tetrahedron Lett. 1997, 38, 3447 10.1016/S0040-4039(97)00642-4
8. Takahashi, K.; Takagi, J.; Ishiyama, T.; Miyaura, N. Chem. Lett. 2000, 29, 126 10.1246/cl.2000.126
9. Chow, W. K.; Yuen, O. Y.; Choy, P. Y.; So, C. M.; Lau, C. P.; Wong, W. T.; Kwong, F. Y. RSC Adv. 2013, 3, 12518 10.1039/c3ra22905j
10. Murata, M. Heterocycles 2012, 85, 1795 10.3987/REV-12-736
11. Pilarski, L. T.; Szabó, K. J. Angew. Chem., Int. Ed. 2011, 50, 8230 10.1002/anie.201102384
12. Merino, P.; Tejero, T. Angew. Chem., Int. Ed. 2010, 49, 7164 10.1002/anie.201003191
13. Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2000, 611, 392 10.1016/S0022-328X(00)00470-8
14. Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2003, 680, 3 10.1016/S0022-328X(03)00176-1
15. Ishiyama, T.; Miyaura, N. Chem. Rec. 2004, 3, 271 10.1002/tcr.10068
16. Ishiyama, T.; Miyaura, N. J. Synth. Org. Chem. Jpn. 1999, 57, 503 10.5059/yukigoseikyokaishi.57.503
17. Ishiyama, T.; Ishida, K.; Miyaura, N. Tetrahedron 2001, 57, 9813 10.1016/S0040-4020(01)00998-X
18. Fürstner, A.; Seidel, G. Org. Lett. 2002, 4, 541 10.1021/ol0171463
19. Billingsley, K. L.; Barder, T. E.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 5359 10.1002/anie.200701551
20. Molander, G. A.; Trice, S. L. J.; Dreher, S. D. J. Am. Chem. Soc. 2010, 132, 17701 10.1021/ja1089759
21. Kawamorita, S.; Ohmiya, H.; Iwai, T.; Sawamura, M. Angew. Chem., Int. Ed. 2011, 50, 8363 10.1002/anie.201103224
22. Chow, W. K.; Yuen, O. Y.; So, C. M.; Wong, W. T.; Kwong, F. Y. J. Org. Chem. 2012, 77, 3543 10.1021/jo202472k
23. Iwai, T.; Harada, T.; Tanaka, R.; Sawamura, M. Chem. Lett. 2014, 43, 584 10.1246/cl.131161
24. Kalläne, S. I.; Teltewskoi, M.; Braun, T.; Braun, B. Organometallics 2015, 34, 1156 10.1021/om500952x
25. Guo, W.-H.; Min, Q.-Q.; Gu, J.-W.; Zhang, X. Angew. Chem., Int. Ed. 2015, 54, 9075 10.1002/anie.201500124
26. Liu, X.-W.; Echavarren, J.; Zarate, C.; Martin, R. J. Am. Chem. Soc. 2015, 137, 12470 10.1021/jacs.5b08103
27. Niwa, T.; Ochiai, H.; Watanabe, Y.; Hosoya, T. J. Am. Chem. Soc. 2015, 137, 14313 10.1021/jacs.5b10119
28. Kinuta, H.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2015, 137, 1593 10.1021/ja511622e
29. Zarate, C.; Manzano, R.; Martin, R. J. Am. Chem. Soc. 2015, 137, 6754 10.1021/jacs.5b03955
30. Block, E. Advances in Sulfur Chemistry; JAI Press: Greenwich, 1994.
31. Cremlyn, R. J. An Introduction of Organosulfur Chemistry; Wiley: Chichester, 1996.
32. Organic Sulfur Chemistry: Biochemical Aspects; Oae, S.; Okuyama, T., Eds.; CRC Press: Boca Raton, 1992.
33. Organic Sulfur Chemistry: Structure and Mechanism; Oae, S., Ed.; CRC Press: Boca Raton, 1991.
34. Luh, T.-Y.; Ni, Z.-J. Synthesis 1990, 1990, 89 10.1055/s-1990-26798
35. Dubbaka, S. R.; Vogel, P. Angew. Chem., Int. Ed. 2005, 44, 7674 10.1002/anie.200463007
36. Prokopcová, H.; Kappe, C. O. Angew. Chem., Int. Ed. 2008, 47, 3674 10.1002/anie.200800449
37. Garnier-Amblard, E. C.; Liebeskind, L. S. Boronic Acids, 2 nd ed.; Hall, D. G., Ed.; Wiley: Weinheim, 2011; Chapter 7.
38. Wang, L.; He, W.; Yu, Z. Chem. Soc. Rev. 2013, 42, 599 10.1039/C2CS35323G
39. Modha, S. G.; Mehta, V. P.; Van der Eycken, E. Chem. Soc. Rev. 2013, 42, 5042 10.1039/c3cs60041f
40. Pan, F.; Shi, Z.-J. ACS Catal. 2014, 4, 280 10.1021/cs400985m
41. Eberhart, A. J.; Imbriglio, J. E.; Procter, D. J. Org. Lett. 2011, 13, 5882 10.1021/ol2025197
42. Melzig, L.; Metzger, A.; Knochel, P. Chem.-Eur. J. 2011, 17, 2948 10.1002/chem.201002850
43. Modha, S. G.; Trivedi, J. C.; Mehta, V. P.; Ermolat'ev, D. S.; Van der Eycken, E. V. J. Org. Chem. 2011, 76, 846 10.1021/jo102089h
44. Koley, M.; Wimmer, L.; Schnürch, M.; Mihovilovic, M. D. Eur. J. Org. Chem. 2011, 2011, 1972 10.1002/ejoc.201001583
45. Dahbi, S.; Bisseret, P. Eur. J. Org. Chem. 2012, 2012, 3759 10.1002/ejoc.201200433
46. Hooper, J. F.; Young, R. D.; Pernik, I.; Weller, A. S.; Willis, M. C. Chem. Sci. 2013, 4, 1568 10.1039/c3sc00052d
47. Pan, F.; Wang, H.; Shen, P.-X.; Zhao, J.; Shi, Z.-J. Chem. Sci. 2013, 4, 1573 10.1039/c3sc22242j
48. Creech, G. S.; Kwon, O. Chem. Sci. 2013, 4, 2670 10.1039/c3sc50773d
49. Liu, J.; Liu, Y.; Du, W.; Dong, Y.; Liu, J.; Wang, M. J. Org. Chem. 2013, 78, 7293 10.1021/jo400984h
50. -1, respectively: Luo, Y.-R. Comprehensive Handbook of Chemical Bond Energies; CRC Press: Boca Raton, 2007.
51. Beletskaya, I. P.; Ananikov, V. P. Eur. J. Org. Chem. 2007, 2007, 3431 10.1002/ejoc.200700119
52. Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205 10.1021/cr9902749
53. Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596 10.1021/cr100347k
54. Eichman, C. C.; Stambuli, J. P. Molecules 2011, 16, 590 10.3390/molecules16010590
55. Liu, H.; Jiang, X. Chem.-Asian J. 2013, 8, 2546 10.1002/asia.201300636
56. Lee, C.-F.; Liu, Y.-C.; Badsara, S. S. Chem.-Asian J. 2014, 9, 706 10.1002/asia.201301500
57. Murakami, K.; Yorimitsu, H.; Osuka, A. Angew. Chem., Int. Ed. 2014, 53, 7510 10.1002/anie.201403288
58. Sugahara, T.; Murakami, K.; Yorimitsu, H.; Osuka, A. Angew. Chem., Int. Ed. 2014, 53, 9329 10.1002/anie.201404355
59. Otsuka, S.; Fujino, D.; Murakami, K.; Yorimitsu, H.; Osuka, A. Chem.-Eur. J. 2014, 20, 13146 10.1002/chem.201404380
60. Otsuka, S.; Yorimitsu, H.; Osuka, A. Chem.-Eur. J. 2015, 21, 14703 10.1002/chem.201502101
61. Gao, K.; Yorimitsu, H.; Osuka, A. Angew. Chem., Int. Ed. 2016, 55, 4573 and references cited therein 10.1002/anie.201600248
62. During the revision of this manuscript, a paper about rhodium-catalyzed ipso-borylation of aryl sulfides appeared: Uetake, Y.; Niwa, T.; Hosoya, T. Org. Lett. 2016, 18, 2758 10.1021/acs.orglett.6b01250
63. Valente, C.; Çalimsiz, S.; Hoi, K. H.; Mallik, D.; Sayah, M.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 3314 10.1002/anie.201106131
64. Valente, C.; Pompeo, M.; Sayah, M.; Organ, M. G. Org. Process Res. Dev. 2014, 18, 180 10.1021/op400278d
65. Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Aldrichimica Acta 2006, 39, 117
66. Peh, G.-R.; Kantchev, E. A. B.; Er, J.-C.; Ying, J. Y. Chem.-Eur. J. 2010, 16, 4010 10.1002/chem.200902842
67. Marion, N.; Nolan, S. P. Acc. Chem. Res. 2008, 41, 1440 10.1021/ar800020y
68. Figuly, G. D.; Loop, C. K.; Martin, J. C. J. Am. Chem. Soc. 1989, 111, 654 10.1021/ja00184a038
69. Smith, K.; Lindsay, C. M.; Pritchard, G. J. J. Am. Chem. Soc. 1989, 111, 665 10.1021/ja00184a040
70. 3 diboron compounds, see: Pietsch, S.; Neeve, E. C.; Apperley, D. C.; Bertermann, R.; Mo, F.; Qiu, D.; Cheung, M. S.; Dang, L.; Wang, J.; Radius, U.; Lin, Z.; Kleeberg, C.; Marder, T. B. Chem.-Eur. J. 2015, 21, 7082 and references cited therein 10.1002/chem.201500235