Cobalt-Catalyzed Benzylic Borylation: Enabling Polyborylation and Functionalization of Remote, Unactivated C(sp3)-H Bonds

Journal of the American Chemical Society

Volumn 138, Issue 3, 2016, Pages 766-769

  Palmer, W Neil ^a   Obligacion, Jennifer V ^a   Pappas, Iraklis ^a   Chirik, Paul J ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CARBOXYLATION; CATALYSIS; COBALT; SYNTHESIS (CHEMICAL);

BASE METALS; BENZYLIC; BORYLATION; C-H ACTIVATION; DIIMINE LIGAND; FUNCTIONALIZATIONS; FUNCTIONALIZED; PINACOLATE;

COBALT COMPOUNDS;

BENZYL DERIVATIVE; CARBON; COBALT; HYDROGEN; TOLUENE;

ARTICLE; BORYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; POLYBORYLATION; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

EID: 84956794725     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b12249     Document Type: Article

References (66)

1. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624 10.1021/cr900005n
2. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147 10.1021/cr900184e
3. Wencel-Delord, J.; Droge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740 10.1039/c1cs15083a
4. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788 10.1021/ar200185g
5. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879 10.1021/cr300153j
6. Mousseau, J. J.; Charette, A. B. Acc. Chem. Res. 2013, 46, 412 10.1021/ar300185z
7. Godula, K.; Sames, D. Science 2006, 312, 67 10.1126/science.1114731
8. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417 10.1038/nature06485
9. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885 10.1039/c1cs15013h
10. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976 10.1039/c0cs00182a
11. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960 10.1002/anie.201201666
12. Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369 10.1038/nchem.1607
13. Ishiyama, T.; Miyaura, N. Pure Appl. Chem. 2006, 78, 1369 10.1351/pac200678071369
14. Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2003, 680, 3 10.1016/S0022-328X(03)00176-1
15. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890 10.1021/cr900206p
16. Hartwig, J. F. Acc. Chem. Res. 2012, 45, 864 10.1021/ar200206a
17. Hall, D. G. Boronic Acids; Wiley-VCH: Weinheim, 2005.
18. Crudden, C. M.; Glasspoole, B. W.; Lata, C. J. Chem. Commun. 2009, 44, 6704 10.1039/b911537d
19. Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995 10.1126/science.287.5460.1995
20. Cho, J.-Y.; Iverson, C. N.; Smith, M. R., III. J. Am. Chem. Soc. 2000, 122, 12868 10.1021/ja0013069
21. Kawamorita, S.; Miyazaki, T.; Ohmiya, H.; Iwai, T.; Sawamura, M. J. Am. Chem. Soc. 2011, 133, 19310 10.1021/ja208364a
22. Furukawa, T.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2015, 137, 12211 10.1021/jacs.5b07677
23. Takaya, J.; Ito, S.; Nomoto, H.; Saito, N.; Kirai, N.; Iwasawa, N. Chem. Commun. 2015, 51, 17662 10.1039/C5CC07263H
24. Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III. Science 2002, 295, 305 10.1126/science.1067074
25. Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390 10.1021/ja0173019
26. Ishiyama, T.; Takagi, J.; Hartwig, J. F.; Miyaura, N. Angew. Chem., Int. Ed. 2002, 41, 3056 10.1002/1521-3773(20020816)41:16<3056::AID-ANIE3056>3.0.CO;2-#
27. Larsen, M. A.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 4287 10.1021/ja412563e
28. Preshlock, S. M.; Ghaffari, B.; Maligres, P. E.; Krska, S. W.; Maleczka, R. E., Jr.; Smith, M. R., III. J. Am. Chem. Soc. 2013, 135, 7572 10.1021/ja400295v
29. Hatanaka, T.; Ohki, Y.; Tatsumi, K. Chem. Asian J. 2010, 5, 1657 10.1002/asia.201000140
30. 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 10.1021/jacs.5b00895
31. Obligacion, J. V.; Semproni, S.; Chirik, P. J. J. Am. Chem. Soc. 2014, 136, 4133 10.1021/ja500712z
32. Schaefer, B. A.; Margulieux, G. W.; Small, B. L.; Chirik, P. J. Organometallics 2015, 34, 1307 10.1021/acs.organomet.5b00044
33. Furukawa, T.; Tobisu, M.; Chatani, N. Chem. Commun. 2015, 51, 6508 10.1039/C5CC01378J
34. Zhang, H.; Hagihara, S.; Itami, K. Chem. Lett. 2015, 44, 779 10.1246/cl.150154
35. Mazzacano, T. J.; Mankad, N. P. J. Am. Chem. Soc. 2013, 135, 17258 10.1021/ja408861p
36. Légaré, M.-A.; Courtemanche, M.-A.; Rochette, é.; Fontaine, F.-G. Science 2015, 349, 513 10.1126/science.aab3591
37. Jones, W. D.; Feher, F. J. Acc. Chem. Res. 1989, 22, 91 10.1021/ar00159a002
38. Kawamorita, S.; Miyazaki, T.; Iwai, T.; Ohmiya, T.; Sawamura, M. J. Am. Chem. Soc. 2012, 134, 12924 10.1021/ja305694r
39. Kawamorita, S.; Murakami, R.; Iwai, T.; Sawamura, M. J. Am. Chem. Soc. 2013, 135, 2947 10.1021/ja3126239
40. Mita, T.; Ikeda, Y.; Michigami, K.; Sato, Y. Chem. Commun. 2013, 49, 5601 10.1039/c3cc42675k
41. Zhang, L.-S.; Chen, G.; Wang, X.; Guo, Q.-Y.; Zhang, X.-S.; Pan, F.; Chen, K.; Shi, Z.-J. Angew. Chem., Int. Ed. 2014, 53, 3899 10.1002/anie.201310000
42. Ohmura, T.; Torigoe, T.; Suginome, M. J. Am. Chem. Soc. 2012, 134, 17416 10.1021/ja307956w
43. Ohmura, T.; Torigo, T.; Suginome, M. Organometallics 2013, 32, 6170 10.1021/om400900z
44. Liskey, C. W.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 3375 10.1021/ja400103p
45. Chen, H.; Hartwig, J. F. Angew. Chem., Int. Ed. 1999, 38, 3391 10.1002/(SICI)1521-3773(19991115)38:22<3391::AID-ANIE3391>3.0.CO;2-N
46. Murphy, J. M.; Lawrence, J. D.; Kawamura, K.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 13684 10.1021/ja064092p
47. Liskey, C. W.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 3375 10.1021/ja400103p
48. Li, Q.; Liskey, C. W.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 8755 10.1021/ja503676d
49. Boebel, T. A.; Hartwig, J. F. Organometallics 2008, 27, 6013 10.1021/om800696d
50. Shimada, S.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Angew. Chem., Int. Ed. 2001, 40, 2168 10.1002/1521-3773(20010601)40:11<2168::AID-ANIE2168>3.3.CO;2-S
51. Mertins, K.; Zapf, A.; Beller, M. J. Mol. Catal. A: Chem. 2004, 207, 21 10.1016/S1381-1169(03)00470-9
52. Ishiyama, T.; Ishida, K.; Takagi, J.; Miyaura, N. Chem. Lett. 2001, 30, 1082 10.1246/cl.2001.1082
53. Cho, S. H.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 8157 10.1021/ja403462b
54. Cho, S. H.; Hartwig, J. F. Chem. Sci. 2014, 5, 694 10.1039/C3SC52824C
55. Larsen, M. A.; Wilson, C. V.; Hartwig, J. F. J. Am. Chem. Soc. 2015, 137, 8633 10.1021/jacs.5b04899
56. Hong, K.; Liu, X.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 10581 10.1021/ja505455z
57. Joannou, M. V.; Moyer, B. S.; Meek, S. J. J. Am. Chem. Soc. 2015, 137, 6176 10.1021/jacs.5b03477
58. Joannou, M. V.; Moyer, B. S.; Goldfogel, M. J.; Meek, S. J. Angew. Chem., Int. Ed. 2015, 54, 14141 10.1002/anie.201507171
59. Endo, K.; Hirokami, M.; Shibata, T. J. Org. Chem. 2010, 75, 3469 10.1021/jo1003407
60. Coombs, J. R.; Zhang, L.; Morken, J. P. Org. Lett. 2015, 17, 1708 10.1021/acs.orglett.5b00480
61. Sun, C.; Potter, B.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 6534 10.1021/ja500029w
62. Potter, B.; Szymaniak, A. A.; Edelstein, E. K.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 17918 10.1021/ja510266x
63. Palmer, W. N.; Diao, T.; Pappas, I.; Chirik, P. J. ACS Catal. 2015, 5, 622 10.1021/cs501639r
64. Zhu, D.; Janssen, F. F. B. J.; Budzelaar, P. H. M. Organometallics 2010, 29, 1897 10.1021/om901045s
65. Scheuermann, M. L.; Johnson, E. J.; Chirik, P. J. Org. Lett. 2015, 17, 2716 10.1021/acs.orglett.5b01135
66. Friedfeld, M. R.; Margulieux, G. W.; Schaefer, B. A.; Chirik, P. J. J. Am. Chem. Soc. 2014, 136, 13178 10.1021/ja507902z