Ancillary metal centers in frustrated lewis pair chemistry: Ruthenium acetylide as a lewis base in the activation of CO2, aldehyde, and alkyne

Organometallics

Volumn 33, Issue 1, 2014, Pages 387-393

  Boone, Michael P ^a   Stephan, Douglas W ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE ADDITION; C-C BONDS; FRUSTRATED LEWIS PAIRS; INDENYL; LEWIS BASE; METAL CENTERS; ORGANIC FRAGMENTS; RUTHENIUM ACETYLIDE;

ALDEHYDES; CARBON DIOXIDE; HYDROCARBONS;

RUTHENIUM;

EID: 84892607822     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om401118n     Document Type: Article

References (82)

1. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46-76
2. Stephan, D. W. Dalton Trans. 2009, 3129-3136
3. Stephan, D. W. Org. Biomol. Chem. 2008, 6, 1535-1539
4. Stephan, D. W.; Erker, G. Top. Curr. Chem. 2013, 332, 85-110
5. Stephan, D. W. Org. Biomol. Chem. 2012, 10, 5740-5746
6. Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124-1126
7. Dobrovetsky, R.; Stephan, D. W. Angew. Chem., Int. Ed. 2013, 52, 2516-2519
8. Sgro, M. J.; Domer, J.; Stephan, D. W. Chem. Commun. 2012, 48, 7253-7255
9. Neu, R. C.; Menard, G.; Stephan, D. W. Dalton Trans. 2012, 41, 9016-9018
10. Lavigne, F.; Maerten, E.; Alcaraz, G.; Branchadell, V.; Saffon-Merceron, N.; Baceiredo, A. Angew. Chem., Int. Ed. 2012, 51, 2489-2491
11. Zhao, X. X.; Stephan, D. W. Chem. Commun. 2011, 47, 1833-1835
12. Peuser, I.; Neu, R. C.; Zhao, X. X.; Ulrich, M.; Schirmer, B.; Tannert, J. A.; Kehr, G.; Frohlich, R.; Grimme, S.; Erker, G.; Stephan, D. W. Chem. Eur. J. 2011, 17, 9640-9650
13. Menard, G.; Stephan, D. W. Angew. Chem., Int. Ed. 2011, 50, 8396-8399
14. Ménard, G.; Stephan, D. W. J. Am. Chem. Soc. 2010, 132, 1796-1797
15. Dureen, M. A.; Stephan, D. W. J. Am. Chem. Soc. 2010, 132, 13559-13568
16. Mömming, C. M.; Otten, E.; Kehr, G.; Fröhlich, R.; Grimme, S.; Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2009, 48, 6643-6646
17. Ashley, A. E.; Thompson, A. L.; O'Hare, D. Angew. Chem., Int. Ed. 2009, 48, 9839-43
18. Sajid, M.; Klose, A.; Birkmann, B.; Liang, L. Y.; Schirmer, B.; Wiegand, T.; Eckert, H.; Lough, A. J.; Frohlich, R.; Daniliuc, C. G.; Grimme, S.; Stephan, D. W.; Kehr, G.; Erker, G. Chem. Sci. 2013, 4, 213-219
19. Stephan, D. W. Top. Curr. Chem. 2013, 332, 1-44
20. Menard, G.; Hatnean, J. A.; Cowley, H. J.; Lough, A. J.; Rawson, J. M.; Stephan, D. W. J. Am. Chem. Soc. 2013, 135, 6446-6449
21. Tolman, W. B. Angew. Chem., Int. Ed. 2010, 49, 1018-1024
22. Otten, E.; Neu, R. C.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 9918-9919
23. Neu, R. C.; Otten, E.; Stephan, D. W. Angew. Chem., Int. Ed. 2009, 48, 9709-9712
24. Sajid, M.; Stute, A.; Cardenas, A. J. P.; Culotta, B. J.; Hepperle, J. A. M.; Warren, T. H.; Schirmer, B.; Grimme, S.; Studer, A.; Daniliuc, C. G.; Frohlich, R.; Petersen, J. L.; Kehr, G.; Erker, G. J. Am. Chem. Soc. 2012, 134, 10156-10168
25. Cardenas, A.; Culotta, B.; Warren, T.; Grimme, S.; Stute, A.; Frohlich, R.; Kehr, G.; Erker, G. Angew. Chem., Int. Ed. 2011, 50, 7567-7571
26. Unverhau, K.; Lubbe, G.; Wibbeling, B.; Frohlich, R.; Kehr, G.; Erker, G. Organometallics 2010, 29, 5320-5329
27. Menard, G.; Tran, L.; Stephan, D. W. Dalton Trans. 2013, 42, 13685-13691
28. Palomas, D.; Holle, S.; Ines, B.; Bruns, H.; Goddard, R.; Alcarazo, M. Dalton Trans. 2012, 41, 9073-9082
29. Ines, B.; Palomas, D.; Holle, S.; Steinberg, S.; Nicasio, J. A.; Alcarazo, M. Angew. Chem., Int. Ed. 2012, 51, 12367-9
30. Iglesias-Siguenza, J.; Alcarazo, M. Angew. Chem., Int. Ed. 2012, 51, 1523-1524
31. Ines, B.; Holle, S.; Goddard, R.; Alcarazo, M. Angew. Chem., Int. Ed. 2010, 49, 8389-8391
32. Alcarazo, M.; Gomez, C.; Holle, S.; Goddard, R. Angew. Chem., Int. Ed. 2010, 49, 5788-5791
33. Runyon, J. W.; Steinhof, O.; Dias, H. V. R.; Calabrese, J. C.; Marshall, W. J.; Arduengo, A. J. Aust. J. Chem. 2011, 64, 1165-1172
34. Li, H.; Aquino, A. A. J.; Cordes, D. B.; Hung-Low, F.; Hase, W. L.; Krempner, C. J. Am. Chem. Soc. 2013, 135, 16066-16069
35. Chapman, A. M.; Wass, D. F. Dalton Trans. 2012, 41, 9067-9072
36. Chapman, A. M.; Haddow, M. F.; Wass, D. F. Eur. J. Inorg. Chem. 2012, 1546-1554
37. Chapman, A. M.; Haddow, M. F.; Wass, D. F. J. Am. Chem. Soc. 2011, 133, 8826-8829
38. Chapman, A. M.; Haddow, M. F.; Wass, D. F. J. Am. Chem. Soc. 2011, 133, 18463-18478
39. Sgro, M. J.; Stephan, D. W. Chem. Commun. 2013, 49, 2610-2612
40. Sgro, M. J.; Stephan, D. W. Angew. Chem., Int. Ed. 2012, 51, 11343-11345
41. Boone, M. P.; Stephan, D. W. J. Am. Chem. Soc. 2013, 135, 8508-8511
42. Boone, M. P.; Stephan, D. W. Organometallics 2011, 30, 5537-5542
43. Bruce, M. I. Chem. Rev. 1991, 91, 197-257
44. Bruce, M.; Humphrey, M. Aust. J. Chem. 1989, 42, 1067-1075
45. Bruce, M. I.; Koutsantonis, G. A.; Liddell, M. J.; Nicholson, B. K. J. Organomet. Chem. 1987, 320, 217-227
46. Bruce, M. I.; Humphrey, M. G.; Snow, M. R.; Tiekink, E. R. T. J. Organomet. Chem. 1986, 314, 213-225
47. Bruce, M. I.; Duffy, D. N.; Humphrey, M. G.; Koutsantonis, G. A. J. Organomet. Chem. 1985, 295, C40-C46
48. Bruce, M. I.; Swincer, A. G. Vinylidene and Propadienylidene (Allenylidene) Metal Complexes. In Advances in Organometallic Chemistry; Stone, F. G. A.; Robert, W., Eds.; Academic Press: New York, 1983; pp 59-128.
49. Bruce, M. I.; Wallis, R. C. Aust. J. Chem. 1979, 32, 1471-85
50. Bruce, M. I.; Wallis, R. C. J. Organomet. Chem. 1978, 161, C1-C4
51. Ullrich, M.; Lough, A. J.; Stephan, D. W. Organometallics 2010, 29, 3647-3654
52. Ullrich, M.; Lough, A. J.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 52-53
53. Neu, R. C.; Menard, G.; Stephan, D. W. Dalton Trans. 2012, 41, 9016-9018
54. Menard, G.; Stephan, D. W. Dalton Trans. 2013, 42, 5447-5453
55. Dureen, M. A.; Brown, C. C.; Stephan, D. W. Organometallics 2010, 29, 6594-6607
56. Dureen, M. A.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 8396-8397
57. Menard, G.; Stephan, D. W. Angew. Chem., Int. Ed. 2012, 51, 8272-8275
58. Ménard, G.; Stephan, D. W. Angew. Chem., Int. Ed. 2011, 50, 8396-8399
59. Mutoh, Y.; Imai, K.; Kimura, Y.; Ikeda, Y.; Ishii, Y. Organometallics 2011, 30, 204-207
60. De Angelis, F.; Sgamellotti, A.; Re, N. Dalton Trans. 2004, 20, 3225-3230
61. De Angelis, F.; Sgamellotti, A.; Re, N. Organometallics 2002, 21, 5944-5950
62. Wakatsuki, Y.; Koga, N.; Werner, H.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 360-366
63. Bustelo, E.; Carbó, J. J.; Lledós, A.; Mereiter, K.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 2003, 125, 3311-3321
64. de los Ríos, I.; Tenorio, M. J.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 1997, 119, 6529-6538
65. Lomprey, J. R.; Selegue, J. P. J. Am. Chem. Soc. 1992, 114, 5518-5523
66. Bullock, R. M. J. Chem. Soc., Chem. Commun. 1989, 0, 165-167
67. Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Ortuño, M. A.; Ujaque, G.; Lledós, A. Inorg. Chem. 2013, 52, 8919-8932
68. Bruneau, C.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2006, 45, 2176-2203
69. Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311-323
70. Bruneau, C. Ruthenium Vinylidenes and Allenylidenes in Catalysis. In Ruthenium Catalysts and Fine Chemistry; Springer: Berlin, Heidelberg: 2004; pp 125-153.
71. Bruneau, C.; Dixneuf, P. H. Metal Vinylidenes and Allenylidenes in Catalysis: From Reactivity to Applications in Synthesis; Wiley-VCH: Weinheim, Germany, 2008.
72. Xu, X.; Frohlich, R.; Daniliuc, C. G.; Kehr, G.; Erker, G. Chem. Commun. 2012, 48, 6109-6111
73. Podiyanachari, S.; Frohlich, R.; Daniliuc, C.; Petersen, J.; Muck-Lichtenfeld, C.; Kehr, G.; Erker, G. Angew. Chem., Int. Ed. 2012, 51, 8830-8833
74. Chen, C.; Fröhlich, R.; Kehr, G.; Erker, G. Chem. Commun. 2010, 46, 3580-3582
75. Emmert, M.; Kehr, G.; Fröhlich, R.; Erker, G. Chem. Eur. J. 2009, 15, 8124-8127
76. Axenov, K.; Kehr, G.; Frohlich, R.; Erker, G. Organometallics 2009, 28, 5148-5158
77. Chen, L.; Kehr, G.; Fröhlich, R.; Erker, G. Eur. J. Inorg. Chem. 2008, 73-83
78. Oro, L. A.; Ciriano, M. A.; Campo, M.; Foces-Foces, C.; Cano, F. H. J. Organomet. Chem. 1985, 289, 117-131
79. Parks, D. J.; Spence, R. E. V. H.; Piers, W. E. Angew. Chem., Int. Ed. 1995, 34, 809-811
80. Hair, G. S.; Cowley, A. H.; Jones, R. A.; McBurnett, B. G.; Voigt, A. J. Am. Chem. Soc. 1999, 121, 4922-4923
81. Apex 2 Software Package; Bruker AXS Inc., Madison, WI, USA, 2013.
82. Cromer, D. T.; Waber, J. T. International Tables of X-Ray Crystallography; Kynoch Press: Dordrecht, The Netherlands, 1974; Vol. 4.