C(sp2)-H Borylation of Fluorinated Arenes Using an Air-Stable Cobalt Precatalyst: Electronically Enhanced Site Selectivity Enables Synthetic Opportunities

Journal of the American Chemical Society

Volumn 139, Issue 7, 2017, Pages 2825-2832

  Obligacion, Jennifer V ^a   Bezdek, Máté J ^a   Chirik, Paul J ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYST SELECTIVITY; FLUORINE;

ANTI-INFLAMMATORY DRUGS; COBALT CATALYST; COBALT PRE CATALYSTS; DIRECTING GROUPS; EFFICIENT SYNTHESIS; PRECIOUS METAL CATALYSTS; SITE SELECTIVITY; SUBSTITUTION PATTERNS;

COBALT COMPOUNDS;

COBALT; DIMETHYLAMINE; FLUORINE; FUNCTIONAL GROUP; POLYCYCLIC AROMATIC HYDROCARBON; AIR; ALKENE; ANTIINFLAMMATORY AGENT; BORON; FLURBIPROFEN; IRIDIUM;

AIR; ARTICLE; BORYLATION; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; ELECTRON; FLUORINATION; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG STABILITY; HALOGENATION;

AIR; ALKENES; ANTI-INFLAMMATORY AGENTS; BORON; CATALYSIS; COBALT; DRUG STABILITY; FLURBIPROFEN; HALOGENATION; IRIDIUM; MOLECULAR STRUCTURE;

EID: 85013861712     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b13346     Document Type: Article

References (50)

1. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881 10.1126/science.1131943
2. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359 10.1021/jm800219f
3. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320 10.1039/B610213C
4. Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832 10.1021/jm401375q
5. Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432 10.1021/cr4002879
6. Jeschke, P. ChemBioChem 2004, 5, 570 10.1002/cbic.200300833
7. Jeschke, P. Pest Manage. Sci. 2010, 66, 10 10.1002/ps.1829
8. Fujiwara, T.; O’Hagan, D. J. Fluorine Chem. 2014, 167, 16 10.1016/j.jfluchem.2014.06.014
9. Babudri, R.; Farinola, G. M.; Naso, F.; Ragni, R. Chem. Commun. 2007, 1003 10.1039/B611336B
10. Berger, R.; Resnati, G.; Metrangolo, P.; Weber, E.; Hulliger, J. Chem. Soc. Rev. 2011, 40, 3496 10.1039/c0cs00221f
11. Hall, D. G. Boronic Acids; Wiley-VCH: Weinheim, Germany, 2005.
12. Mkhalid, I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig Chem. Rev. 2010, 110, 890 10.1021/cr900206p
13. Hartwig, J. F. Chem. Soc. Rev. 2011, 40, 1992 10.1039/c0cs00156b
14. Hartwig, J. F. Acc. Chem. Res. 2012, 45, 864 10.1021/ar200206a
15. Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III Science 2002, 295, 305 10.1126/science.1067074
16. Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390 10.1021/ja0173019
17. 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-#
18. Preshlock, S. M.; Ghaffari, B.; Maligres, P. E.; Krska, S. W.; Maleczka, R. E.; Smith, M. R. J. Am. Chem. Soc. 2013, 135, 7572 10.1021/ja400295v
19. Boller, T. M.; Murphy, J. M.; Hapke, M.; Ishiyama, T.; Miyaura, N.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 14263 10.1021/ja053433g
20. Tamura, H.; Yamazaki, H.; Sato, H.; Sakaki, S. J. Am. Chem. Soc. 2003, 125, 16114 10.1021/ja0302937
21. Green, A. G.; Liu, P.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 4575 10.1021/ja411699u
22. Hall, G. E.; Piccolini, R.; Roberts, J. D. J. Am. Chem. Soc. 1955, 77, 4540 10.1021/ja01622a033
23. Streitwieser, A., Jr.; Scannon, P. J.; Niemeyer, H. M. J. Am. Chem. Soc. 1972, 94, 7936 10.1021/ja00777a053
24. Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581 10.1021/ja055819x
25. Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754 10.1021/ja062509l
26. Jayasundara, C. R. K.; Unold, J. M.; Oppenheimer, J.; Smith, M. R., III.; Maleczka, R. E. Org. Lett. 2014, 16, 6072 10.1021/ol5028738
27. Furukawa, T.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2015, 137, 12211 10.1021/jacs.5b07677
28. Takaya, J.; Ito, S.; Nomoto, H.; Saito, N.; Kirai, N.; Iwasawa, N. Chem. Commun. 2015, 51, 17662 10.1039/C5CC07263H
29. Kalläne, S. I.; Teltewskoi, M.; Braun, T.; Braun, B. Organometallics 2015, 34, 1156 10.1021/om500952x
30. Esteruelas, M. A.; Olivan, M.; Vélez, A. Organometallics 2015, 34, 1911 10.1021/acs.organomet.5b00176
31. Smith, M. R.; Maleczka, R. E.; Li, H.; Jayasundara, C.; Oppenheimer, J.; Sabasovs, D. U.S. Patent Application 61/874,249.
32. Chirik, P. J.; Wieghardt, K. Science 2010, 327, 794 10.1126/science.1183281
33. Obligacion, J. V.; Semproni, S. P.; Chirik, P. J. J. Am. Chem. Soc. 2014, 136, 4133 10.1021/ja500712z
34. Obligacion, J. V.; Semproni, S. P.; Pappas, I.; Chirik, P. J. J. Am. Chem. Soc. 2016, 138, 10645 10.1021/jacs.6b06144
35. Scheuermann, M. L.; Johnson, E. J.; Chirik, P. J. Org. Lett. 2015, 17, 2716 10.1021/acs.orglett.5b01135
36. Palmer, W. N.; Obligacion, J. V.; Pappas, I.; Chirik, P. J. J. Am. Chem. Soc. 2016, 138, 766 10.1021/jacs.5b12249
37. Schuster, C. H.; Diao, T.; Pappas, I.; Chirik, P. J. ACS Catal. 2016, 6, 2632 10.1021/acscatal.6b00304
38. Constable, E. C.; Housecroft, C. E.; Jullien, V.; Neuburger, M.; Schaffner, S. Inorg. Chem. Commun. 2006, 9, 504 10.1016/j.inoche.2006.01.018
39. Léonard, N. G.; Bezdek, M.; Chirik, P. J. Organometallics 2017, 36, 142 10.1021/acs.organomet.6b00630
40. Pappas, I.; Treacy, S.; Chirik, P. J. ACS Catal. 2016, 6, 4105 10.1021/acscatal.6b01134
41. Noda, D.; Tahara, A.; Sunada, Y.; Nagashima, H. J. Am. Chem. Soc. 2016, 138, 2480 10.1021/jacs.5b11311
42. Aromí, G.; Batsanov, A. S.; Christian, P.; Helliwell, M.; Parkin, A.; Parsons, S.; Smith, A. A.; Timco, G. A.; Winpenny, R. E. P. Chem.-Eur. J. 2003, 9, 5142 10.1002/chem.200304993
43. Boebel, T. A.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 7534 10.1021/ja8015878
44. Ros, A.; Estepa, B.; López-Rodriguez, R.; Álvarez, E.; Fernández, R.; Lassaletta, J. M. Angew. Chem., Int. Ed. 2011, 50, 11724 10.1002/anie.201104544
45. Roering, A. J.; Hale, L. V. A.; Squier, P. A.; Ringgold, M. A.; Wiederspan, E. R.; Clark, T. B. Org. Lett. 2012, 14, 3558 10.1021/ol301635x
46. In a study that compares the regioselectivities of Rh-catalyzed C-H silylation and Ir-catalyzed C-H borylation, the C-H borylation reaction of p-fluorotoluene (7d) with iridium was reported to exclusively undergo borylation ortho to fluorine. See the following: Cheng, C.; Hartwig, J. F. Science 2014, 343, 853 10.1126/science.1248042
47. The iridium-catalyzed C-H borylation of p-fluorotrifluoromethoxy benzene (7f) resulted in borylation ortho to fluorine with 97% selectivity. See the following: Batool, F.; Parveen, S.; Emwas, A.-H.; Sioud, S.; Gao, X.; Munawar, M. A.; Chotana, G. A. Org. Lett. 2015, 17, 4256 10.1021/acs.orglett.5b02050
48. Liskey, C. W.; Liao, X.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 11389 10.1021/ja104442v
49. Durandetti, M.; Gosmini, C.; Périchon, J. Tetrahedron 2007, 63, 1146 10.1016/j.tet.2006.11.055
50. Quasdorf, K. W.; Riener, M.; Petrova, K. V.; Garg, N. K. J. Am. Chem. Soc. 2009, 131, 17748 10.1021/ja906477r