Iron(II) Active Species in Iron-Bisphosphine Catalyzed Kumada and Suzuki-Miyaura Cross-Couplings of Phenyl Nucleophiles and Secondary Alkyl Halides

Journal of the American Chemical Society

Volumn 137, Issue 35, 2015, Pages 11432-11444

  Daifuku, Stephanie L ^a   Kneebone, Jared L ^a   Snyder, Benjamin E R ^a   Neidig, Michael L ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL REACTIONS; COUPLINGS; DICHROISM; MAGNETIC COUPLINGS; NUCLEOPHILES; SPECTROSCOPIC ANALYSIS;

CROSS-COUPLED PRODUCT; KUMADA CROSS-COUPLING; MAGNETIC CIRCULAR DICHROISMS; PRIMARY ALKYL HALIDES; REDUCTIVE ELIMINATION; SPECTROSCOPIC STUDIES; SUZUKI-MIYAURA CROSS-COUPLING; SUZUKI-MIYAURA REACTION;

IRON;

ELECTROPHILE; FERROUS ION; HALIDE; IRON; NUCLEOPHILE; ALKANE; BORIC ACID; HALOGEN; ORGANOMETALLIC COMPOUND; PHOSPHINE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CROSS COUPLING REACTION; ELECTRON SPIN RESONANCE; ELIMINATION REACTION; REACTION ANALYSIS; SPECTROSCOPY; SUZUKI REACTION; CHEMISTRY; OXIDATION REDUCTION REACTION;

ALKANES; BORIC ACIDS; CATALYSIS; HALOGENS; IRON; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PHOSPHINES;

EID: 84941242954     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b06648     Document Type: Article

References (58)

1. Bolm, C.; Legros, J.; Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217 10.1021/cr040664h
2. Sherry, B. D.; Furstner, A. Acc. Chem. Res. 2008, 41, 1500 10.1021/ar800039x
3. Czaplik, W. M.; Mayer, M.; Cvengros, J.; Wangelin, A. J. v. ChemSusChem 2009, 2, 396-417 10.1002/cssc.200900055
4. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417-1492 10.1021/cr100327p
5. Bauer, I.; Knolker, H.-J. Chem. Rev. 2015, 115, 3170-3387 10.1021/cr500425u
6. Nakamura, E.; Yoshikai, N. J. Org. Chem. 2010, 75, 6061-6067 10.1021/jo100693m
7. Tamura, M.; Kochi, J. K. J. Am. Chem. Soc. 1971, 93, 1487-1489 10.1021/ja00735a030
8. Tamura, M.; Kochi, J. K. J. Organomet. Chem. 1971, 31, 289-309 10.1016/S0022-328X(00)86239-7
9. Neumann, S. M.; Kochi, J. K. J. Org. Chem. 1975, 40, 599-606 10.1021/jo00893a013
10. Smith, R. S.; Kochi, J. K. J. Org. Chem. 1976, 41, 502-509 10.1021/jo00865a019
11. Tamura, M.; Kochi, J. K. Bull. Chem. Soc. Jpn. 1971, 44, 3063-3073 10.1246/bcsj.44.3063
12. Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686-3687 10.1021/ja049744t
13. Guerinot, A.; Reymond, S.; Cossy, J. Angew. Chem., Int. Ed. 2007, 46, 6521-6524 10.1002/anie.200702206
14. Cahiez, G.; Duplais, C.; Moyeaux, A. Org. Lett. 2007, 9, 3253-3254 10.1021/ol7016092
15. Noda, D.; Sunada, Y.; Hatakeyama, T.; Nakamura, M.; Nagashima, H. J. Am. Chem. Soc. 2009, 131, 6078-6079 10.1021/ja901262g
16. Bedford, R. B.; Brenner, P. B.; Carter, E.; Cogswell, P. M.; Haddow, M. F.; Harvey, J. N.; Murphy, D. M.; Nunn, J.; Woodall, C. H. Angew. Chem., Int. Ed. 2014, 53, 1804-1808 10.1002/anie.201308395
17. Hedstroem, A.; Izakian, Z.; Vreto, I.; Wallentin, C.-J.; Norrby, P.-O. Chem.-Eur. J. 2015, 21, 5946-5953 10.1002/chem.201406096
18. Bedford, R. B.; Betham, M.; Bruce, D. W.; Danopoulos, A. A.; Frost, R. M.; Hird, M. J. Org. Chem. 2006, 71, 1104-1110 10.1021/jo052250+
19. Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc. 2007, 129, 9844-9845 10.1021/ja073084l
20. Hatakeyama, T.; Hashimoto, S.; Ishizuka, K.; Nakamura, M. J. Am. Chem. Soc. 2009, 131, 11949-11963 10.1021/ja9039289
21. Ghorai, S.; Jin, M.; Hatakeyama, T.; Nakamura, M. Org. Lett. 2012, 14, 1066-1069 10.1021/ol2031729
22. Guisan-Ceinos, M.; Tato, F.; Bunuel, E.; Calle, P.; Cardenas, D. J. Chem. Sci. 2013, 4, 1098-1104 10.1039/c2sc21754f
23. Li, B.-J.; Xu, L.; Wu, Z.-H.; Guan, B.-T.; Sun, C.-L.; Wang, B.-Q.; Shi, Z.-J. J. Am. Chem. Soc. 2009, 131, 14656-14657 10.1021/ja907281f
24. Furstner, A.; Martin, R.; Krause, H.; Seidel, G.; Goddard, R.; Lehmann, C. W. J. Am. Chem. Soc. 2008, 130, 8773-8787 10.1021/ja801466t
25. Kuzmina, O. M.; Steib, A. K.; Flubacher, D.; Knochel, P. Org. Lett. 2012, 14, 4818-4821 10.1021/ol302136c
26. Kuzmina, O. M.; Steib, A. K.; Markiewicz, J. T.; Flubacker, D.; Knochel, P. Angew. Chem., Int. Ed. 2013, 52, 4945-4949 10.1002/anie.201210235
27. Agrawal, T.; Cook, S. P. Org. Lett. 2013, 15, 96-99 10.1021/ol303130j
28. Mo, Z.; Zhang, Q.; Deng, L. Organometallics 2012, 31, 6518-6521 10.1021/om300722g
29. Steib, A.; Thaler, T.; Komeyama, K.; Mayer, P.; Knochel, P. Angew. Chem., Int. Ed. 2011, 50, 3303-3307 10.1002/anie.201007187
30. Bauer, G.; Wodrich, M. D.; Scopelliti, R.; Hu, X. Organometallics 2015, 34, 289-298 10.1021/om501122p
31. Furstner, A.; Leitner, A.; Mendez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856-13863 10.1021/ja027190t
32. Scheiper, B.; Bonnekessel, M.; Krause, H.; Furstner, A. J. Org. Chem. 2004, 69, 3943-3949 10.1021/jo0498866
33. Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297-1299 10.1021/ol049779y
34. Martin, R.; Furstner, A. Angew. Chem., Int. Ed. 2004, 43, 3955-3957 10.1002/anie.200460504
35. Bedford, R. B.; Huwe, M.; Wilkinson, M. C. Chem. Commun. 2009, 600-602 10.1039/B818961G
36. Adams, C. J.; Bedford, R. B.; Carter, E.; Gower, N. J.; Haddow, M. F.; Harvey, J. N.; Huwe, M.; Cartes, M. A.; Mansell, S. M.; Mendoza, C.; Murphy, D. M.; Neeve, E. C.; Nunn, J. J. Am. Chem. Soc. 2012, 134, 10333-10336 10.1021/ja303250t
37. Hatakeyama, T.; Kondo, Y.; Fujiwara, Y.; Takaya, H.; Ito, S.; Nakamura, E.; Nakamura, M. Chem. Commun. 2009, 1216-1218 10.1039/b820879d
38. Dongol, K. G.; Koh, H.; Sau, M.; Chai, C. L. L. Adv. Synth. Catal. 2007, 349, 1015-1018 10.1002/adsc.200600383
39. Hatakeyama, T.; Hashimoto, T.; Kathriarachchi, K. K. A. D. S.; Zenmyo, T.; Seike, H.; Nakamura, M. Angew. Chem., Int. Ed. 2012, 51, 8834-8837 10.1002/anie.201202797
40. Bedford, R. B.; Carter, E.; Cogswell, P. M.; Gower, N. J.; Haddow, M. F.; Harvey, J. N.; Murphy, D. M.; Neeve, E. C.; Nunn, J. Angew. Chem., Int. Ed. 2013, 52, 1285-1288 10.1002/anie.201207868
41. Bedford, R. B.; Brenner, P. B.; Carter, E.; Carvell, T. W.; Cogswell, P. M.; Gallagher, T.; Harvey, J. N.; Murphy, D. M.; Neeve, E. C.; Nunn, J.; Pye, D. R. Chem.-Eur. J. 2014, 20, 7935-7938 10.1002/chem.201402174
42. Hatakeyama, T.; Hashimoto, T.; Kondo, Y.; Fujiwara, Y.; Seike, H.; Takaya, H.; Tamad, Y.; Ono, T.; Nakamura, M. J. Am. Chem. Soc. 2010, 132, 10674-10676 10.1021/ja103973a
43. Hatakeyama, T.; Fujiwara, Y.; Okada, Y.; Itoh, T.; Hashimoto, T.; Kawamura, S.; Ogata, K.; Takaya, H.; Nakamura, M. Chem. Lett. 2011, 40, 1030-1032 10.1246/cl.2011.1030
44. Hatakeyama, T.; Okada, Y.; Yoshimoto, Y.; Nakamura, M. Angew. Chem., Int. Ed. 2011, 50, 10973-10976 10.1002/anie.201104125
45. Sun, C.-L.; Krause, H.; Furstner, A. Adv. Synth. Catal. 2014, 356, 1281-1291 10.1002/adsc.201301089
46. Kawamura, S.; Nakamura, M. Chem. Lett. 2013, 42, 183-185 10.1246/cl.2013.183
47. Nakagawa, N.; Hatakeyama, T.; Nakamura, M. Chem. Lett. 2015, 44, 486-488 10.1246/cl.141167
48. Hashimoto, T.; Hatakeyama, T.; Nakamura, M. J. Org. Chem. 2012, 77, 1168-1173 10.1021/jo202151f
49. Takaya, H.; Nakajima, S.; Nakagawa, N.; Isozaki, K.; Iwamoto, T.; Imayoshi, R.; Gower, N. J.; Adak, L.; Hatakeyama, T.; Honma, T.; Masafumi, M.; Sunada, T.; Nagashima, H.; Hashizume, D.; Takahashi, O.; Nakamura, M. Bull. Chem. Soc. Jpn. 2015, 88, 410-418 10.1246/bcsj.20140376
50. Daifuku, S. L.; Al-Afyouni, M. H.; Snyder, B. E. R.; Kneebone, J. L.; Neidig, M. L. J. Am. Chem. Soc. 2014, 136, 9132-9143 10.1021/ja503596m
51. Hawrelak, E. J.; Bernskoetter, W. H.; Lobkovsky, E.; Yee, G. T.; Bill, E.; Chirik, P. J. Inorg. Chem. 2005, 44, 3103-3111 10.1021/ic048202+
52. Bedford, R. B. Acc. Chem. Res. 2015, 48, 1485-1493 10.1021/acs.accounts.5b00042
53. Bedford, R. B.; Brenner, P. B.; Carter, E.; Clifton, J.; Cogswell, P. M.; Gower, N. J.; Haddow, M. F.; Harvey, J. N.; Kehl, J. A.; Murphy, D. M.; Neeve, E. C.; Neidig, M. L.; Nunn, J.; Snyder, B. E. R.; Taylor, J. Organometallics 2014, 33, 5767-5780 10.1021/om500518r
54. Pavel, E. G.; Kitajima, N.; Solomon, E. I. J. Am. Chem. Soc. 1998, 120, 3949-3962 10.1021/ja973735l
55. Fillman, K. L.; Przyojski, J. A.; Al-Afyouni, M. H.; Tonzetich, Z.; Neidig, M. L. Chem. Sci. 2015, 6, 1178-1188 10.1039/C4SC02791D
56. Hedstrom, A.; Lindstedt, E.; Norrby, P.-O. J. Organomet. Chem. 2013, 748, 51-55 10.1016/j.jorganchem.2013.04.024
57. Winter, G.; Thompson, D. W.; Loehe, J. R. Inorg. Synth. 1973, 14, 99-104
58. Neese, F.; Solomon, E. I. Inorg. Chem. 1999, 38, 1847-1865 10.1021/ic981264d