Formation of C-C bonds via rutheniumcatalyzed transfer hydrogenation

Pure and Applied Chemistry

Volumn 84, Issue 8, 2012, Pages 1729-1739

  Moran, Joseph ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

C C bond formation; Catalysis; Ruthenium catalysis; Transfer hydrogenation

Indexed keywords

BOND FORMING; C-C BOND FORMATION; C-C BONDS; CARBONYL ADDITION; ENANTIOSELECTIVE; ORGANOMETALLIC REAGENT; OXIDATION LEVEL; PRIMARY ALCOHOLS; REDUCTANTS; RUTHENIUM CATALYSIS; TRANSFER HYDROGENATIONS;

ALDEHYDES; CATALYSIS; ORGANOMETALLICS; RUTHENIUM;

HYDROGENATION;

EID: 84864490215     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/PAC-CON-11-10-18     Document Type: Article

References (91)

1. C. D. Frohning, C. W. Kohlpaintner. In Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1, B. Cornils, W. A. Herrmann (Eds.), pp. 29-104, Wiley-VCH, Weinheim (1996).
2. P. W. N. M. van Leeuwen. Homogeneous Catalysis: Understanding the Art, Kluwer, Dordrecht (2004).
3. For a review of ruthenium-catalyzed alkene hydroformylation, see: P. Kalck, Y. Peres, J. Jenck. Adv. Organomet. Chem. 32, 121 (1991).
4. R. L. Patman, J. F. Bower, I. S. Kim, M. J. Krische. Aldrichim. Acta 41, 95 (2008).
5. J. F. Bower, I. S. Kim, R. L. Patman, M. J. Krische. Angew. Chem., Int. Ed. 48, 34 (2009).
6. S. B. Han, I. S. Kim, M. J. Krische. Chem. Commun. 7278 (2009).
7. J. F. Bower, M. J. Krische. Top. Organomet. Chem. 34, 107 (2011).
8. T. D. Nixon, M. K. Whittlesey, J. M. J. Williams. Dalton Trans. 753 (2009).
9. G. E. Dobereiner, R. H. Crabtree. Chem. Rev. 110, 681 (2010).
10. G. Guillena, D. J. Ramón, M. Yus. Chem. Rev. 110, 1611 (2010).
11. For a previous review on ruthenium-catalyzed transfer hydrogenative C-C bond formation, see: F. Shibahara, M. J. Krische. Chem. Lett. 37, 1102 (2008).
12. B. M. Trost, F. D. Toste, A. B. Pinkerton. Chem. Rev. 101, 2067 (2001).
13. T. Kondo, T.-a. Mitsudo. Curr. Org. Chem. 6, 1163 (2002).
14. S. Derien, F. Monnier, P. H. Dixneuf. Top. Organomet. Chem. 11, 1 (2004).
15. Y. Tsuji, T. Mukai, T. Kondo, Y. Watanabe. J. Organomet. Chem. 369, C51 (1989).
16. T. Kondo, H. Ono, N. Satake, T.-a. Mitsudo, Y. Watanabe. Organometallics 14, 1945 (1995).
17. C.-M. Yu, S. Lee, Y.-T. Hong, S.-K. Yoon. Tetrahedron Lett. 45, 6557 (2004).
18. S. Omura, T. Fukuyama, J. Horiguchi, Y. Murakami, I. Ryu. J. Am. Chem. Soc. 130, 14094 (2008).
19. S. E. Denmark, S. T. Nguyen. Org. Lett. 11, 781 (2009).
20. P. V. Ramachandran. Aldrichim. Acta 35, 23 (2002).
21. S. E. Denmark, J. Fu. Chem. Rev. 103, 2763 (2003).
22. C.-M. Yu, J. Youn, H.-K. Jung. Bull. Kor. Chem. Soc. 27, 463 (2006).
23. I. Marek, G. Sklute. Chem. Commun. 1683 (2007).
24. D. G. Hall. Synlett 1644 (2007).
25. H. Lachance, D. G. Hall. Org. React. 73, 1 (2008).
26. For selected reviews of carbonyl allylation based on the reductive coupling of metallo-u-allyls derived from allylic alcohols, ethers, or carboxylates, see: (a) Y. Masuyama. "Palladium-catalyzed carbonyl allylation via c-allylpalladium complexes", in Advances in Metal-Organic Chemistry, Vol. 3, L. S. Liebeskind (Ed.), pp. 255-303, JAI Press, Greenwich (1994).
27. Y. Tamaru. "Palladium-catalyzed reactions of allyl and related derivatives with organo-electrophiles", in Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 2, E.-i. Negishi, A. de Meijere (Eds.), pp. 1917-1943, John Wiley, New York (2002).
28. Y. Tamaru. J. Organomet. Chem. 576, 215 (1999).
29. T. Kondo, T.-a. Mitsudo. Curr. Org. Chem. 6, 1163 (2002).
30. Y. Tamaru. Eur. J. Org. Chem. 2647 (2005).
31. G. Zanoni, A. Pontiroli, A. Marchetti, G. Vidari. Eur. J. Org. Chem. 3599 (2007).
32. A. Fürstner, N. Shi. J. Am. Chem. Soc. 118, 2533 (1996).
33. M. Avalos, R. Babiano, P. Cintas, J. L. Jiménez, J. C. Palacios. Chem. Soc. Rev. 28, 169 (1999).
34. M. Bandini, P. G. Cozzi, A. Umani-Ronchi. Chem. Commun. 919 (2002).
35. G. C. Hargaden, P. J. Guiry. Adv. Syn. Catal. 349, 2407 (2007).
36. M. Inoue, T. Suzuki, A. Kinoshita, M. Nakada. Chem. Rec. 8, 169 (2008).
37. E. Skucas, J. F. Bower, M. J. Krische. J. Am. Chem. Soc. 129, 12678 (2007).
38. J. F. Bower, E. Skucas, R. L. Patman, M. J. Krische. J. Am. Chem. Soc. 129, 15134 (2007).
39. J. F. Bower, R. L. Patman, M. J. Krische. Org. Lett. 10, 1033 (2008).
40. S. B. Han, I. S. Kim, H. Han, M. J. Krische. J. Am. Chem. Soc. 131, 6916 (2009).
41. J. R. Zbieg, T. Fukuzumi, M. J. Krische. Adv. Synth. Catal. 352, 2416 (2010).
42. M.-Y. Ngai, E. Skucas, M. J. Krische. Org. Lett. 10, 2705 (2008).
43. J. R. Zbieg, E. L. McInturff, J. C. Leung, M. J. Krische. J. Am. Chem. Soc. 133, 1141 (2011).
44. E. Skucas, J. R. Zbieg, M. J. Krische. J. Am. Chem. Soc. 131, 5054 (2009).
45. J. R. Zbieg, E. L. McInturff, M. J. Krische. Org. Lett. 12, 2514 (2010).
46. F. Shibahara, J. F. Bower, M. J. Krische. J. Am. Chem. Soc. 130, 6338 (2008).
47. F. Shibahara, J. F. Bower, M. J. Krische. J. Am. Chem. Soc. 130, 14120 (2008).
48. S. Omura, T. Fukuyama, J. Horiguchi, Y. Murakami, I. Ryu. J. Am. Chem. Soc. 130, 14094 (2008).
49. J. R. Zbieg, J. Moran, M. J. Krische. J. Am. Chem. Soc. 133, 10582 (2011).
50. P. Isnard, B. Denise, R. P. A. Sneeden, J. M. Cognion, P. Durual. J. Organomet. Chem. 240, 285 (1982).
51. P. Isnard, B. Denise, R. P. A. Sneeden, J. M. Cognion, P. Durual. J. Organomet. Chem. 256, 135 (1983).
52. T. Kondo, Y. Tsuji, Y. Watanabe. Tetrahedron Lett. 28, 6229 (1987).
53. T. Kondo, M. Akazome, Y. Tsuji, Y. Watanabe. J. Org. Chem. 55, 1286 (1990).
54. T. Kondo, N. Hiraishi, Y. Morisaki, K. Wada, Y. Watanabe, T.-A Mitsudo. Organometallics 17, 2131 (1998).
55. T. Smejkal, H. Han, B. Breit, M. J. Krische. J. Am. Chem. Soc. 131, 10366 (2009).
56. H. Han, M. J. Krische. Org. Lett. 12, 2844 (2009).
57. F. Sato, M. Kusakabe, Y. Kobayashi. J. Chem. Soc., Chem. Commun. 1131 (1984).
58. M. D. Helm, P. Mayer, P. Knochel. Chem. Commun. 1916 (2008).
59. For a recent review of carbonyl vinylation, see: M. C. Kauffman, P. J. Walsh. In Science of Synthesis, Stereoselective Synthesis, Vol. 2, G. A. Molander (Ed.), pp. 449-495, Thieme, Stuttgart (2011).
60. I. Ojima, M. Tzamarioudaki, C.-Y. Tsai. J. Am. Chem. Soc. 116, 3643 (1994).
61. W. E. Crowe, M. J. Rachita. J. Am. Chem. Soc. 117, 6787 (1995).
62. N. M. Kablaoui, S. L. Buchwald. J. Am. Chem. Soc. 117, 6785 (1995).
63. E. Oblinger, J. Montgomery. J. Am. Chem. Soc. 119, 9065 (1997).
64. X.-Q. Tang, J. Montgomery. J. Am. Chem. Soc. 121, 6098 (1999).
65. X.-Q. Tang, J. Montgomery. J. Am. Chem. Soc. 122, 6950 (2000).
66. G. M. Mahandru, G. Liu, J. Montgomery. J. Am. Chem. Soc. 126, 3698 (2004).
67. B. Knapp-Reed, G. M. Mahandru, J. Montgomery. J. Am. Chem. Soc. 127, 13156 (2005).
68. M. R. Chaulagain, G. J. Sormunen, J. Montgomery. J. Am. Chem. Soc. 129, 9568 (2007).
69. H. A. Malik, G. J. Sormunen, J. Montgomery. J. Am. Chem. Soc. 132, 6304 (2010).
70. W.-S. Huang, J. Chan, T. F. Jamison. Org. Lett. 2, 4221 (2000).
71. K. M. Miller, W.-S. Huang, T. F. Jamison. J. Am. Chem. Soc. 125, 3442 (2003).
72. K. M. Miller, T. F. Jamison. Org. Lett. 7, 3077 (2005).
73. K. Takai, S. Sakamoto, T. Isshiki. Org. Lett. 5, 653 (2003).
74. J.-R. Kong, M.-Y. Ngai, M. J. Krische. J. Am. Chem. Soc. 128, 718 (2006).
75. C.-W. Cho, M. J. Krische. Org. Lett. 8, 3873 (2006).
76. Y.-T. Hong, C.-W. Cho, E. Skucas, M. J. Krische. Org. Lett. 9, 3745 (2007).
77. V. Komanduri, M. J. Krische. J. Am. Chem. Soc. 128, 16448 (2006).
78. P. Liu, M. J. Krische, K. N. Houk. Chem.-Eur. J. 17, 4021 (2011).
79. Y. Musashi, S. Sakaki. J. Am. Chem. Soc. 124, 7588 (2002).
80. V. M. Williams, J.-R. Kong, B.-J. Ko, Y. Mantri, J. S. Brodbelt, M.-H. Baik, M. J. Krische. J. Am. Chem. Soc. 131, 16054 (2009).
81. J.-R. Kong, C.-W. Cho, M. J. Krische. J. Am. Chem. Soc. 127, 11269 (2005).
82. R. L. Patman, M. R. Chaulagain, V. M. Williams, M. J. Krische. J. Am. Chem. Soc. 131, 2066 (2009).
83. V. M. Williams, J. C. Leung, R. L. Patman, M. J. Krische. Tetrahedron 65, 5024 (2009).
84. C. C. Bausch, R. L. Patman, B. Breit, M. J. Krische. Angew. Chem., Int. Ed. 50, 5687 (2011).
85. J. C. Leung, R. L. Patman, B. Sam, M. J. Krische. Chem.-Eur. J. 17, 12437 (2011).
86. J.-L. Moreau. The Chemistry of Ketenes, Allenes and Related Compounds, S. Patai (Ed.), pp. 363-413, John Wiley, New York (1980).
87. J. A. Marshall. Chem. Rev. 96, 31 (1996).
88. B. W. Gung. Org. React. 64, 1 (2004).
89. J. A. Marshall, B. W. Gung, M. L. Grachan. Modern Allene Chemistry, N. Krause, A. S. K. Hashmi (Eds.), pp. 493-592, Wiley-VCH, Weinheim (2004).
90. J. A. Marshall. J. Org. Chem. 72, 8153 (2007).
91. R. L. Patman, V. M. Williams, J. F. Bower, M. J. Krische. Angew. Chem., Int. Ed. 47, 5220 (2008).