Cyclopropanation/Carboboration Reactions of Enynes with B(C6F5)3

Journal of the American Chemical Society

Volumn 137, Issue 49, 2015, Pages 15469-15477

  Hansmann, Max M ^a   Melen, Rebecca L ^b   Rudolph, Matthias ^a   Rominger, Frank ^a   Wadepohl, Hubert ^a   Stephan, Douglas W ^c   Hashmi, A Stephen K ^a,d  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b CARDIFF UNIVERSITY   (United Kingdom)

^c UNIVERSITY OF TORONTO   (Canada)

^d KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; CHEMICAL ACTIVATION;

1 ,6-ENYNES; ALKENE MOIETIES; CYCLOPROPANATION; FRUSTRATED LEWIS PAIRS; LEWIS ACID; RING OPENING; STEREOSPECIFIC; STOICHIOMETRIC REACTION;

HYDROCARBONS;

ALKENE; ALKYNE; BORON; CARBON; CYCLOHEXANE DERIVATIVE; CYCLOPENTANE; CYCLOPROPANE; LEWIS ACID;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; CYCLOPROPANATION; DIASTEREOISOMER; RING OPENING; STOICHIOMETRY; SUBSTITUTION REACTION;

EID: 84950341872     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b09311     Document Type: Article

References (69)

1. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281 10.1002/anie.199502591
2. Trost, B. M. Science 1991, 254, 1471-1477 10.1126/science.1962206
3. Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636-1638 10.1021/ja00213a054
4. Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42 10.1021/ar00170a004
5. Trost, B. M.; Krische, M. J. Synlett 1998, 1998, 1-16 10.1055/s-1998-1557
6. Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096 10.1021/cr000666b
7. Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813 10.1021/cr980054f
8. Ma, S.; Yu, S.; Gu, Z. Angew. Chem., Int. Ed. 2006, 45, 200-203 10.1002/anie.200502999
9. Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271-2296 10.1002/adsc.200600368
10. Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326-3350 10.1021/cr0684319
11. Michelet, V.; Toullec, P. Y.; Genêt, J.-P. Angew. Chem., Int. Ed. 2008, 47, 4268-4315 10.1002/anie.200701589
12. Toullec, P.; Michelet, V. In Computational Mechanisms of Au and Pt Catalyzed Reactions; Soriano, E.; Marco-Contelles, J., Eds.; Springer: Berlin Heidelberg, 2011; Vol. 302, p 31.
13. Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553-11554 10.1021/ja005570d
14. Power, P. P. Nature 2010, 463, 171-177 10.1038/nature08634
15. Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124-1126 10.1126/science.1134230
16. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46-76 10.1002/anie.200903708
17. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2015, 54, 6400-6441 10.1002/anie.201409800
18. McCahill, J. S. J.; Welch, G. C.; Stephan, D. W. Angew. Chem., Int. Ed. 2007, 46, 4968-4971 10.1002/anie.200701215
19. Dureen, M. A.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 8396-8397 10.1021/ja903650w
20. Melen, R. L.; Hansmann, M. M.; Lough, A. J.; Hashmi, A. S. K.; Stephan, D. W. Chem.-Eur. J. 2013, 19, 11928-11938 10.1002/chem.201301899
21. Hansmann, M. M.; Melen, R. L.; Rominger, F.; Hashmi, A. S. K.; Stephan, D. W. J. Am. Chem. Soc. 2014, 136, 777-782 10.1021/ja4110842
22. Hansmann, M. M.; Melen, R. L.; Rominger, F.; Hashmi, A. S. K.; Stephan, D. W. Chem. Commun. 2014, 50, 7243-7245 10.1039/c4cc01370k
23. Chen, C.; Harhausen, M.; Liedtke, R.; Bussmann, K.; Fukazawa, A.; Yamaguchi, S.; Petersen, J. L.; Daniliuc, C. G.; Frohlich, R.; Kehr, G.; Erker, G. Angew. Chem., Int. Ed. 2013, 52, 5992-5996 10.1002/anie.201300871
24. Melen, R. L. Chem. Commun. 2014, 50, 1161-1174 10.1039/C3CC48036D
25. Lee, S. I.; Chatani, N. Chem. Commun. 2009, 371-384 10.1039/B812466C
26. Bour, C.; Gandon, V. Synlett 2015, 26, 1427 10.1055/s-0034-1380712
27. Jiang, C. F.; Blacque, O.; Berke, H. Organometallics 2010, 29, 125-133 10.1021/om9008636
28. Chen, C.; Kehr, G.; Fröhlich, R.; Erker, G. J. Am. Chem. Soc. 2010, 132, 13594-13595 10.1021/ja106365j
29. Kehr, G.; Erker, G. Chem. Commun. 2012, 48, 1839-1850 10.1039/C1CC15628D
30. Chen, C.; Eweiner, F.; Wibbeling, B.; Fröhlich, R.; Senda, S.; Ohki, Y.; Tatsumi, K.; Grimme, S.; Kehr, G.; Erker, G. Chem.-Asian J. 2010, 5, 2199-2208 10.1002/asia.201000189
31. Chen, C.; Voss, T.; Fröhlich, R.; Kehr, G.; Erker, G. Org. Lett. 2011, 13, 62-65 10.1021/ol102544x
32. Ekkert, O.; Kehr, G.; Fröhlich, R.; Erker, G. Chem. Commun. 2011, 47, 10482-10484 10.1039/c1cc13008k
33. Ekkert, O.; Kehr, G.; Fröhlich, R.; Erker, G. J. Am. Chem. Soc. 2011, 133, 4610-4616 10.1021/ja1110283
34. Ekkert, O.; Tuschewitzki, O.; Daniliuc, C. G.; Kehr, G.; Erker, G. Chem. Commun. 2013, 49, 6992-6994 10.1039/c3cc43294g
35. Feldhaus, P.; Kehr, G.; Fröhlich, R.; Daniliuc, C. G.; Erker, G. Z. Naturforsch., B: J. Chem. Sci. 2013, 68, 666-674 10.5560/znb.2013-3088
36. Liedtke, R.; Harhausen, M.; Fröhlich, R.; Kehr, G.; Erker, G. Org. Lett. 2012, 14, 1448-1451 10.1021/ol300193e
37. Mobus, J.; Bonnin, Q.; Ueda, K.; Fröhlich, R.; Itami, K.; Kehr, G.; Erker, G. Angew. Chem., Int. Ed. 2012, 51, 1954-1957 10.1002/anie.201107398
38. Tsao, F. A.; Lough, A. J.; Stephan, D. W. Chem. Commun. 2015, 51, 4287-4289 10.1039/C4CC09258A
39. Tsao, F. A.; Stephan, D. W. Dalton Trans. 2015, 44, 71-74 10.1039/C4DT03241A
40. Liedtke, R.; Tenberge, F.; Daniliuc, C. G.; Kehr, G.; Erker, G. J. Org. Chem. 2015, 80, 2240-2248 10.1021/jo502753s
41. Ge, F.; Kehr, G.; Daniliuc, C. G.; Erker, G. Organometallics 2015, 34, 229-235 10.1021/om501085j
42. Eller, C.; Kehr, G.; Daniliuc, C. G.; Erker, G. Chem. Commun. 2015, 51, 8436-8438 10.1039/C5CC00734H
43. Eller, C.; Kehr, G.; Daniliuc, C. G.; Stephan, D. W.; Erker, G. Chem. Commun. 2015, 51, 7226-7229 10.1039/C5CC01806D
44. Cade, I. A.; Ingleson, M. J. Chem.-Eur. J. 2014, 20, 12874-12880 10.1002/chem.201403614
45. Devillard, M.; Brousses, R.; Miqueu, K.; Bouhadir, G.; Bourissou, D. Angew. Chem., Int. Ed. 2015, 54, 5722-5726 10.1002/anie.201500959
46. Melen, R. L.; Wilkins, L. C.; Kariuki, B. M.; Wadepohl, H.; Gade, L. H.; Hashmi, A. S. K.; Stephan, D. W.; Hansmann, M. M. Organometallics 2015, 34, 4127-4137 10.1021/acs.organomet.5b00546
47. Feldmann, A.; Iida, A.; Fröhlich, R.; Yamaguchi, S.; Kehr, G.; Erker, G. Organometallics 2012, 31, 2445-2451 10.1021/om300065m
48. Feldmann, A.; Kehr, G.; Daniliuc, C. G.; Muck-Lichtenfeld, C.; Erker, G. Chem.-Eur. J. 2015, 21, 12456-12464 10.1002/chem.201502278
49. Warner, A. J.; Lawson, J. R.; Fasano, V.; Ingleson, M. J. Angew. Chem., Int. Ed. 2015, 54, 11245 10.1002/anie.201505810
50. Dorel, R.; Echavarren, A. M. J. Org. Chem. 2015, 80, 7321 10.1021/acs.joc.5b01106
51. Brooner, R. E. M.; Brown, T. J.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2013, 52, 6259 10.1002/anie.201301640
52. Fürstner, A.; Morency, L. Angew. Chem., Int. Ed. 2008, 47, 5030-5033 10.1002/anie.200800934
53. Nieto-Oberhuber, C.; López, S.; Jiménez-Núñez, E.; Echavarren, A. M. Chem.-Eur. J. 2006, 12, 5916 10.1002/chem.200600174
54. Soriano, E.; Marco-Contelles, J. J. Org. Chem. 2005, 70, 9345-9353 10.1021/jo0514265
55. Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305-8314 10.1021/ja981183g
56. Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104 10.1021/ja981877p
57. Chen, J.; Reibenspies, J.; Derecskei-Kovacs, A.; Burgess, K. Chem. Commun. 1999, 2501-2502 10.1039/a907559c
58. Hsee, L. C.; Sardella, D. J. Magn. Reson. Chem. 1990, 28, 688-692 10.1002/mrc.1260280806
59. Hierso, J.-C. Chem. Rev. 2014, 114, 4838-4867 10.1021/cr400330g
60. Zhao, X.; Stephan, D. W. J. Am. Chem. Soc. 2011, 133, 12448-12450 10.1021/ja205598k
61. Hill, E. A.; Park, Y.-W. J. Organomet. Chem. 1988, 356, 1-16 10.1016/0022-328X(88)80667-3
62. Pei, W.; Krauss, I. J. J. Am. Chem. Soc. 2011, 133, 18514-18517 10.1021/ja2048682
63. Morton, J. G. M.; Dureen, M. A.; Stephan, D. W. Chem. Commun. 2010, 46, 8947-8949 10.1039/c0cc02862b
64. Welch, G. C.; Stephan, D. W. J. Am. Chem. Soc. 2007, 129, 1880-1881 10.1021/ja067961j
65. Mömming, C. M.; Otten, E.; Kehr, G.; Fröhlich, R.; Grimme, S.; Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2009, 48, 6643-6646 10.1002/anie.200901636
66. Marco-Martínez, J.; Buñuel, E.; López-Durán, R.; Cárdenas, D. J. Chem.-Eur. J. 2011, 17, 2734-2741 10.1002/chem.201001124
67. Marco-Martínez, J.; López-Carrillo, V.; Buñuel, E.; Simancas, R.; Cárdenas, D. J. J. Am. Chem. Soc. 2007, 129, 1874-1875 10.1021/ja0685598
68. Pardo-Rodríguez, V.; Marco-Martínez, J.; Buñuel, E.; Cárdenas, D. J. Org. Lett. 2009, 11, 4548-4551 10.1021/ol9017694
69. Chen, C.; Voss, T.; Fröhlich, R.; Kehr, G.; Erker, G. Org. Lett. 2011, 13, 62-65 10.1021/ol102544x