Chemoselective coupling of 1,1-bis[(pinacolato)boryl]alkanes for the transition-metal-frec borylation of aryl and vinyl halides: A combined experimental and theoretical investigation

Journal of the American Chemical Society

Volumn 139, Issue 2, 2017, Pages 975-984

  Lee, Yeosan ^a   Baek, Seung Yeol ^b,c   Park, Jinyoung ^a   Kim, Seoung Tae ^b,c   Tussupbayev, Samat ^b,c   Kim, Jeongho ^a   Baik, Mu Hyun ^b,c   Cho, Seung Hwan ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^c Institute for Basic Science   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BORON; PARAFFINS; TRANSITION METALS;

CHEMO-SELECTIVITY; CHEMOSELECTIVE COUPLING; ORGANOHALIDES; REACTION MECHANISM; TERT-BUTOXIDE; THEORETICAL INVESTIGATIONS; THEORETICAL STUDY; VINYL HALIDES;

METAL HALIDES;

ALKANE DERIVATIVE; ALKOXIDE BASE; ALPHA BORYLCARBANION; ANION; BASE; BORON; BORON DERIVATIVE; FUNCTIONAL GROUP; HALIDE; LEWIS BASE; ORGANOBORON DERIVATIVE; ORGANOHALOGEN DERIVATIVE; SODIUM DERIVATIVE; SODIUM TERT BUTOXIDE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; BORYLATION; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMOSELECTIVITY; CONTROLLED STUDY; CROSS COUPLING REACTION; CYCLOADDITION; NUCLEOPHILICITY; STEREOCHEMISTRY; STEREOSELECTIVITY; THEORETICAL STUDY;

EID: 85018260298     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b11757     Document Type: Article

References (86)

1. Lee, J. C. H.; McDonald, R.; Hall, D. G. Nat. Chem. 2011, 3, 894.
2. Feng, X.; Jeon, H.; Yun, J. Angew. Chem., Int. Ed. 2013, 52, 3989.
3. Lee, J. C. H.; Sun, H.-Y.; Hall, D. G. J. Org. Chem. 2015, 80, 7134.
4. Endo, K.; Ohkubo, T.; Hirokami, M.; Shibata, T. J. Am. Chem. Soc. 2010, 132, 11033.
5. Endo, K.; Ohkubo, T.; Shibata, T. Org. Lett. 2011, 13, 3368.
6. Endo, K.; Ohkubo, T.; Ishioka, T.; Shibata, T. J. Org. Chem. 2012, 77, 4826.
7. Endo, K.; Ishioka, T.; Shibata, T. Synlett 2014, 25, 2184.
8. For transition-metal-catalyzed C-C bond forming reactions of l, l-bis[(pinacolato) boryl]alkanes with organohalides, sec: (a) Sun, C.; Potter, B.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 6534.
9. Potter, B.; Szymaniak, A A.; Edelstein, E. K.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 17918.
10. Sun, H.-Y.; Kubota, K.; Hall, D. G. Chem. - Eur. J. 2015, 21, 19186.
11. Li, H.; Zhang, Z.; Shangguan, X.; Huang, S.; Chen, J.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2014, 53, 11921.
12. Cui, L.-C.; Zhang, Z.-Q.; Lu, X.; Xiao, B.; Fu, Y. RSC Adv. 2016, 6, 51932.
13. For transition-metal-catalyzed C-C bond forming reactions of l, l-bis[(pinacolato) boryl]alkanes with other electrophiles, sec: (a) Zhang, Z.-Q.; Yang, C.-T.; Liang, L.-J.; Xiao, B.; Lu, X.; Liu, J.-H.; Sun, Y.-Y.; Marder, T. B.; Fu, Y. Org. Lett. 2014, 16, 6342.
14. Joannou, M. V.; Moyer, B. S.; Meck, S. J. J. Am. Chem. Soc. 2015, 137, 6176.
15. Joannou, M. V.; Moyer, B. S.; Goldfogel, M. J.; Meck, S. J. Angew. Chem., Int. Ed. 2015, 54, 14141.
16. Xu, S.; Shangguan, X.; Li, H.; Zhang, Y.; Wang, J. J. Org. Chem. 2015, 80, 7779.
17. Shi, Y.; Hoveyda, A H. Angew. Chem., Int. Ed. 2016, 55, 3455.
18. Zhang, Z-Q.; Zhang, B.; Lu, X.; Liu, J.-H.; Lu, X.-Y.; Xiao, B.; Fu, Y. Org. Lett. 2016, 18, 952.
19. Zhan, M.; Li, R.-Z.; Mou, Z.-D.; Cao, C.-G.; Liu, J.; Chen, Y.-W.; Niu, D. ACS Catal. 2016, 6, 3381.
20. Ebrahim-Alkhalil, A.; Zhang, Z.-Q.; Gong, T.-J.; Su, W.; Lu, X.-Y.; Xiao, B.; Fu, Y. Chem. Commun. 2016, 52, 4891.
21. For transition-metal-frec C-C bond forming reactions of 1, 1-bis[(pinacolato) boryl]alkanes, sec: (a) Hong, K.; Liu, X.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 10581.
22. Coombs, J. R.; Zhang, L.; Morken, J. V. J. Am. Chem. Soc. 2014, 136, 16140.
23. Kim, J.; Park, S.; Park, J.; Cho, S. H. Angew. Chem., Int. Ed. 2016, 55, 1498.
24. Park, J.; Lee, Y.; Kim, J.; Cho, S. H. Org. Lett. 2016, 18, 1210.
25. Jo, W.; Kim, J.; Choi, S.; Cho, S. H. Angew. Chem., Int. Ed. 2016, 55, 9690.
26. Kim, J.; Cho, S. H. Synlett 2016, 27, 2525.
27. Hall, D. G. Boronic Acids; Wiley-VCH: Weinheim, Germany, 2005.
28. Suzuki, A.; Brown, H. C. Organic Synthesis via Boranes; Aldrich: Milwaukec, WI, 2003.
29. Brown, H. C.; Cole, T. E. Organometallics 1983, 2, 1316.
30. For selected examples of transition-metal-catalyzed borylation of organo (pseudo) halides: (a) Ishiyama, T.; Miyaura, N. Chem. Rec. 2004, 3, 271.
31. Miyaura, N. Bull. Chem. Soc. Jpn. 2008, 81, 1535.
32. 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.
33. Klecberg, C.; Dang, L.; Lin, Z.; Marder, T. B. Angew. Chem., Int. Ed. 2009, 48, 5350.
34. Molander, G. A.; Trice, S. L. J.; Dreher, S. D. J. Am. Chem. Soc. 2010, 132, 17701.
35. Yamamoto, T.; Morita, T.; Takagi, J.; Yamakawa, T. Org. Lett. 2011, 13, 5766.
36. Nagashima, Y.; Takita, R.; Yoshida, K.; Hirano, K.; Uchiyama, M. J. Am. Chem. Soc. 2013, 135, 18730.
37. Bose, S. K.; Marder, T. B. Org. Lett. 2014, 76, 4562.
38. Liu, X-W.; Echavarren, J.; Zarate, C.; Martin, R. J. Am. Chem. Soc. 2015, 137, 12470.
39. Niwa, T.; Ochiai, H.; Watanabe, Y.; Hosoya, T. J. Am. Chem. Soc. 2015, 137, 14313.
40. Zarate, C.; Manzano, R.; Martin, R. J. Am. Chem. Soc. 2015, 137, 6754.
41. Tobisu, M.; Kinuta, H.; Kita, Y.; Rémond, E.; Chatani, N. J. Am. Chem. Soc. 2012, 134, 115.
42. Tobisu, M.; Nakamura, K.; Chatani, N. J. Am. Chem. Soc. 2014, 136, 5587.
43. For selected examples of C-H borylations: (a) Mkhalid, I. A I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890.
44. Hartwig, J. F. Acc. Chem. Res. 2012, 45, 864.
45. Ros, A.; Fernández, R.; Lassaletta, J. M. Chem. Soc. Rev. 2014, 43, 3229.
46. Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III. Science 2002, 295, 305.
47. Dombray, T.; Werncke, C. G.; Jiang, S.; Grellier, M.; Vendier, L.; Bontemps, S.; Sortais, J.-B.; Sabo-Etienne, S.; Darcel, C. J. Am. Chem. Soc. 2015, 137, 4062.
48. Furukawa, T.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2015, 137, 12211.
49. Kuninobu, Y.; Ida, H.; Nishi, M.; Kanai, M. Nat. Chem. 2015, 7, 712.
50. Légaré, M.-A.; Courtemanche, M.-A.; Rochette, É.; Fontaine, F.-G. Science 2015, 349, 513.
51. Smith, K T.; Berritt, S.; González-Moreiras, M.; Ahn, S.; Smith, M. R., III.; Baik, M.-H.; Mindiola, D. J. Science 2016, 351, 1424.
52. For selected examples of electrophilic borylations: (a) De Vries, T. S.; Prokofjevs, A.; Vedejs, E. Chem. Rev. 2012, 112, 4246.
53. Ingleson, M. J. Synlett 2012, 23, 1411.
54. Ingleson, M. J. Top. Organomet. Chem. 2015, 49, 39.
55. Stahl, T.; Müther, K.; Ohki, Y.; Tatsumi, K.; Oestreich, M. J. Am. Chem. Soc. 2013, 135, 10978.
56. For examples of transition-metal-frec borylations: (a) Mo, F.; Jiang, Y.; Qiu, D.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2010, 49, 1846.
57. Zhu, C.; Yamane, M. Org. Lett. 2012, 14, 4560.
58. Qju, D.; Jin, L.; Zheng, Z.; Meng, H.; Mo, F.; Wang, X.; Zhang, Y.; Wang, J. J. Org. Chem. 2013, 78, 1923.
59. Zhang, J.; Wu, H.-H.; Zhang, J. Eur. J. Org. Chem. 2013, 2013, 6263.
60. Yu, J.; Zhang, L.; Yan, G. Adv. Synth. Catal. 2012, 354, 2625.
61. Erb, W.; Hellal, A.; Albini, M.; Rouden, J.; Blanchet, J. Chem. - Eur. J. 2014, 20, 6608.
62. Miralies, N.; Romero, R. M.; Fernández, E.; Muñiz, K Chem. Commun. 2015, 51, 14068.
63. Mfuh, A M.; Doyle, J. D.; Chhetri, B.; Arman, H. D.; Larionov, O. V. J. Am. Chem. Soc. 2016, 738, 2985.
64. Chen, K.; Zhang, S.; He, P.; Li, P. Chem. Sci. 2016, 7, 3676.
65. Chen, K.; Cheung, M. S.; Lin, Z.; Li, P. Org. Chem. Front. 2016, 3, 875.
66. Yamamoto, E.; Izumi, K.; Horita, Y.; Ito, H. J. Am. Chem. Soc. 2012, 134, 19997.
67. Yamamoto, E.; Ukigai, S.; Ito, H. Chem. Sci. 2015, 6, 2943.
68. Uematsu, R.; Yamamoto, E.; Maeda, S.; Ito, H.; Taketsugu, T. J. Am. Chem. Soc. 2015, 737, 4090.
69. Winkler, H. J. S.; Winkler, H. J. Am. Chem. Soc. 1966, 88, 964.
70. Winkler, H. J. S.; Winkler, H. J. Am. Chem. Soc. 1966, 88, 969.
71. Rogers, H. R.; Houk, J. J. Am. Chem. Soc. 1982, 104, 522.
72. Farnham, W. B.; Calabrese, J. C. J. Am. Chem. Soc. 1986, 708, 2449.
73. Harada, T.; Katsuhira, T.; Oku, A J. Org. Chem. 1992, 57, 5805.
74. Beak, P.; Alen, D. J. J. Am. Chem. Soc. 1992, 774, 3420.
75. Ando, K. J. Org. Chem. 2006, 77, 1837.
76. Cheung, M. S.; Marder, T. B.; Lin, Z. Organometallics 2011, 30, 3018.
77. Tissandier, M. D.; Cowen, K. A.; Feng, W. Y.; Gundlach, E.; Cohen, M. J.; Earhart, A D.; Coe, J. V. J. Phys. Chem. A 1998, 102, 7787.
78. Camaioni, D. M.; Schwerdtfeger, C. A J. Phys. Chem. A 2005, 109, 10795.
79. For selected examples of aryl radical generation from aryl iodides in the presence of alkoxide base: (a) Shirakawa, E.; Itoh, K.; Higashino, T.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 15537.
80. Qiu, Y.; Liu, Y.; Yang, K.; Hong, W.; Li, Z.; Wang, Z.; Yao, Z.; Jiang, S. Org. Lett. 2011, 13, 3556.
81. Wei, W.; Dong, X.; Nie, S.; Chen, Y.; Zhang, X.; Yan, M. Org. Lett. 2013, 15, 6018.
82. Chen, Y.; Zhang, X.; Yuan, H.; Wei, W.; Yan, M. Chem. Commun. 2013, 49, 10974.
83. Drapeau, M. P.; Fabre, L.; Grimaud, L.; Ciofini, I.; Ollevier, T.; Taillefer, M. Angew. Chem., Int. Ed. 2015, 54, 10587.
84. Barham, J. P.; Coulthard, G.; Emery, K. J.; Doni, E.; Cumine, F.; Nocera, G.; John, M. P.; Berlouis, L. E. A.; McGuire, T.; Turtle, T.; Murphy, J. A J. Am. Chem. Soc. 2016, 138, 7402.
85. Annunziata, A.; Galli, C.; Marinelli, M.; Pau, T. Eur. J. Org. Chem. 2001, 2001, 1323.
86. Bose, S. K.; Fucke, K.; Liu, L.; Stecl, P. G.; Marder, T. B. Angew. Chem., Int. Ed. 2014, 53, 1799.