Enthalpy- vs entropy-driven complexation of homoallylic alcohols by rhodium(I) complexes

Organometallics

Volumn 30, Issue 22, 2011, Pages 6233-6240

  Kang, Sung Ok ^a,c   Lynch, Vincent M ^a   Day, Victor W ^b   Anslyn, Eric V ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b UNIVERSITY OF KANSAS   (United States)

^c OAK RIDGE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTALLOGRAPHIC DATA; H NMR SPECTROSCOPY; HOMOALLYLIC ALCOHOL; ISOTHERMAL TITRATION CALORIMETRY; NMR TITRATION; RH COMPLEXES; RHODIUM COMPLEXES; THERMODYNAMIC PARAMETER;

ENTHALPY; ENTROPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RHODIUM; THERMODYNAMICS; TITRATION;

RHODIUM COMPOUNDS;

EID: 81755168924     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200793p     Document Type: Article

References (73)

1. Modern Rhodium-Catalyzed Organic Reactions: Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005.
2. Tarui, A.; Sato, K.; Omote, M.; Kumadaki, I.; Ando, A. Adv. Synth. Catal. 2010, 352, 2733-2744
3. Gual, A.; Godard, C.; Castillon, S.; Carmen, C. Tetrahedron: Asymmetry 2010, 21, 1135-1146
4. Edwards, H. J.; Hargrave, J. D.; Penrose, S. D.; Frost, C. G. Chem. Soc. Rev. 2010, 39, 2093-2105
5. Minnaard, A. J.; Feringa, B. L.; Lefort, L.; de Vries, J. G. Acc. Chem. Res. 2007, 40, 1267-1277
6. Topics in Current Chemistry; Krische, M. J., Ed.; Springer-Verlag: Berlin, 2007; Vol. 279.
7. Modern Organonickel Chemistry; Tamaru, Y., Ed.; Wiley-VCH: Weinheim, 2005.
8. Zhao, P.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 9642-9643
9. Sumida, Y.; Takada, Y.; Hayashi, S.; Hirano, K.; Yorimitsu, H.; Oshima, K. Chem. Asian J. 2008, 3, 119-125
10. Ahisten, N.; Martin-Matute, B. Adv. Synth. Catal. 2009, 351, 2657-2666
11. Rosenberg, S.; Leino, R. Tetrahedron Lett. 2009, 50, 5305-5307
12. Shintani, R.; Takatsu, K.; Hayashi, T. Org. Lett. 2008, 10, 1191-1193
13. Jang, M.; Hayashi, S.; Hirano, K.; Yrimitsu, H.; Oshima, K. Tetrahedron Lett. 2007, 48, 4003-4005
14. Takada, Y.; Hayashi, S.; Hirano, K.; Yrimitsu, H.; Oshima, K. Org. Lett. 2006, 8, 2515-2517
15. Han, S. B.; Kim, I. S.; Krische, M. J. Chem. Commun. 2009, 7278-7287
16. Bower, J. F.; Kim, I. S.; Patman, R. L.; Krische, M. J. Angew. Chem., Int. Ed. 2009, 48, 34-46
17. Ngai, M.-Y.; Kong, J.-R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063-1072
18. Jang, H.-Y.; Krische, M. J. Acc. Chem. Res. 2004, 37, 653-661
19. Tamaru, Y.; Kimura, M. Org. Synth. 2006, 83, 88-96
20. Kimura, M.; Nojiri, D.; Fukushima, M.; Oi, S.; Sonoda, Y.; Inoue, Y. Org. Lett. 2009, 11, 3794-3797
21. Bing, Y.; Menard, F.; Isono, N.; Lautens, M. Synthesis 2009, 853-859
22. Vasylyev, M.; Alper, H. J. Org. Chem. 2010, 75, 2710-2713
23. Christmann, M.; Braese, S., Eds. Asymmetric Synthesis-The Essentials; Wiley-VCH: Weinheim, Germany, 2007.
24. Lin, G.-Q.; Li, Y.-M.; Chan, A. S. C. Principles and Applications of Asymmetric Synthesis; Wiley: New York, 2001.
25. Leung, D.; Folmer-Andersen, J. F.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 2008, 130, 12318-12327
26. Leung, D.; Anslyn, E. V. J. Am. Chem. Soc. 2008, 130, 12328-12333
27. Folmer-Andersen, J. F.; Kitamura, M.; Anslyn, E. V. J. Am. Chem. Soc. 2006, 128, 5652-5653
28. Zhu, L.; Shabbir, S. H.; Anslyn, E. V. Chem.-Eur. J. 2006, 13, 99-104
29. Shabbir, S. H.; Regan, C. J.; Anslyn, E. V. Proc. Natl. Acad. Sci. 2009, 106, 10487-10492
30. Nieto, S.; Lynch, V. M.; Anslyn, E. V.; Kim, H.; Chin, J. J. Am. Chem. Soc. 2008, 130, 9232-9233
31. Mei, X.; Wolf, C. J. Am. Chem. Soc. 2006, 128, 13326-13327
32. Liu, S.; Pestano, J. P. C.; Wolf, C. J. Org. Chem. 2008, 73, 4267-4270
33. Holmes, A. E.; Zahn, S.; Canary, J. W. Chirality 2002, 14, 471-477
34. Zhang, J.; Holmes, A. E.; Sharma, A.; Brooks, N. R.; Rarig, R. S.; Zubieta, J.; Canary, J. W. Chirality 2003, 15, 180-189
35. Corradini, R.; Paganuzzi, C.; Marchelli, R.; Pagliari, S.; Sforza, S.; Dossena, A.; Galaverna, G.; Duchateau, A. J. Mater. Chem. 2005, 15, 2741-2746
36. Corradini, R.; Paganuzzi, C.; Marchelli, R.; Pagliari, S.; Dossena, A.; Duchateau, A. J. Inclusion Phenom. Macrocycl. Chem. 2007, 57, 625-630
37. Tsukamoto, M.; Kagan, H. B. Adv. Synth. Catal. 2002, 344, 453-463
38. Finn, M. G. Chirality 2002, 14, 534-540
39. Pu, L. Chem. Rev. 2004, 104, 1687-1716
40. Charbonneau, V.; Ogilvie, W. W. Mini-Rev. Org. Chem. 2005, 2, 313-332
41. Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284-310
42. Loch, J. A.; Crabtree, R. H. Pure Appl. Chem. 2001, 73, 119-128
43. Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem.-Eur. J. 1998, 4, 1885-1889
44. Sprout, C. M.; Richmond, M. L.; Seto, C. T. J. Org. Chem. 2005, 70, 7408-7417
45. He, X; Zhang, Q.; Wang, W.; Lin, L.; Liu, X.; Feng, X. Org. Lett. 2011, 13, 804-807
46. Germain, M. E.; Temprado, M.; Castonguay, A.; Kryatova, O. P.; Rybak-Akimova, E. V.; Curley, J. J.; Mendiratta, A.; Tsai, Y.-C.; Cummins, C. C.; Prabhakar, R.; McDonough, J. E.; Hoff, C. D. J. Am. Chem. Soc. 2009, 131, 15412-15423
47. Achord, P.; Fujita, E.; Muckerman, J. T.; Scott, B.; Fortman, G. C.; Temprado, M.; Cai, X.; Captain, B.; Isrow, D.; Weir, J. J.; McDonough, J. E.; Hoff, C. D. Inorg. Chem. 2009, 48, 7891-7904
48. Fortman, G. C.; Captain, B.; Hoff, C. D. Inorg. Chem. 2009, 48, 1808-1810
49. Sonnenberger, D. C.; Morss, L. R.; Marks, T. J. Organometallics 1985, 4, 352-355
50. Schock, L. E.; Marks, T. J. J. Am. Chem. Soc. 1988, 110, 7701-7715
51. Nolan, S. P.; Stern, D.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 7844-7853
52. Deck, P. A.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 6128-6129
53. Smith, D. C., Jr.; Stevens, E. D.; Nolan, S. P. Inorg. Chem. 1999, 38, 5277-5281
54. Wang, K.; Goldman, A. S.; Li, C.; Nolan, S. P. Organometallics 1995, 14, 4010-4013
55. Maar, C. M.; Huang, J.; Nolan, S. P. Organometallics 1998, 17, 5018-5024
56. Huang, J.; Haar, C. M.; Nolan, S. P.; Marshall, W. J.; Moloy, K. G. J. Am. Chem. Soc. 1998, 120, 7806-7815
57. Serron, S.; Nolan, S. P. Organometallics 1996, 15, 4301-4306
58. Blackmond, D. G. Angew. Chem., Int. Ed. 2005, 44, 4302-4320
59. Burke, N. E.; Singhal, A.; Hintz, M. J.; Ley, J. A.; Hui, H.; Smith, L. R.; Blake, D. M. J. Am. Chem. Soc. 1979, 101, 74-79
60. Jesse, A. C.; Cordfunke, E. H. P.; Ouweltjes, W. Thermochim. Acta 1979, 30, 293-302
61. Hynes, M. J. J. Chem. Soc., Dalton Trans. 1993, 311-312
62. Job, P. Ann. Chim. 1928, 9, 113-203
63. Blanda, M. T.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1989, 54, 4626-4636
64. Stodeman, M.; Wadso, I. Pure Appl. Chem. 1995, 67, 1059-1068
65. Wadso, I. Trends Biotechnol. 1986, 4, 45-51
66. Wiseman, T.; Williston, S.; Brandts, J. F.; Lin, L. N. Anal. Biochem. 1989, 179, 131-137
67. Bondi, A. J. Phys. Chem. 1964, 68, 441-452
68. Rowland, R. S.; Taylor, R. J. Phys. Chem. 1996, 100, 7384-7391
69. Baenziger, N. C.; Mottel, E. A.; Doyle, J. R. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1991, C47, 539-541
70. Dahlenburg, L.; Osthoff, N.; Heinemann, F. W. Acta Crystallogr., Sect. E: Struct. Rep. 2001, E57, m117-m118
71. Kölle, U.; Görissen, R.; Wagner, T. Chem. Ber. 1995, 128, 911-917
72. Yin, F.; Cao, R.; Goddard, A.; Zhang, Y.; Oldfield, E. J. Am. Chem. Soc. 2006, 128, 3524-3525
73. Bravard, F.; Rosset, C.; Delangle, P. Dalton Trans. 2004, 2012-2018