Transition metal catalyzed manipulation of non-polar carbon-hydrogen bonds for synthetic purpose

Proceedings of the Japan Academy Series B: Physical and Biological Sciences

Volumn 87, Issue 5, 2011, Pages 230-241

  Murai, Shinji ^a  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

Addition to olefin; C H activation; Carbon hydrogen bond; Catalytic reaction; Ruthenium complex; Transition metal catalyst

Indexed keywords

CARBON; ORGANIC COMPOUND; TRANSITION ELEMENT;

CATALYSIS; CHEMISTRY; CYCLIZATION; HYDROGEN BOND; REVIEW; SYNTHESIS;

CARBON; CATALYSIS; CYCLIZATION; HYDROGEN BONDING; ORGANIC CHEMICALS; TRANSITION ELEMENTS;

EID: 79957710246     PISSN: 03862208     EISSN: 13492896     Source Type: Journal    
DOI: 10.2183/pjab.87.230     Document Type: Review

References (96)

1. Kleiman, J.P. and Dubeck, M. (1963) The preparation of cyclopentadienyl [o-(phenylazo)phenyl]-nickel. J. Am. Chem. Soc. 85, 1544-1545.
2. 2. J. Chem. Soc., 2545-2549.
3. Chatt, J. and Davidson, J.M. (1965) The tautomerism of arene and ditertiary phosphine complexes of ruthenium(0), and the preparation of new types of hydrido-complex of ruthenium(II). J. Chem. Soc., 843-855.
4. 6 complex: structure of dichlorotris(triphenylphosphine) ruthenium(II). Inorg. Chem. 4, 778- 783.
5. Bergman, R.G. (1984) Activation of alkanes with organotransition metal complexes. Science 223, 902-908.
6. Shilov, A.E. and Shul'pin, G.B. (1997) Activation of C-H bonds by metal complexes. Chem. Rev. 97, 2879-2932.
7. Jones, W.D. (1999) Activation of C-H bonds: stoichiometric reactions. In Topics in Organometallic Chemistry Vol. 3 (ed. Murai, S.). Springer, Berlin, pp. 9-46.
8. Rhone-Poulenc (1967) Dimerization of acrylonitrile to 1,4-dicyanobutene and (or) adiponitrile. Neth. Patent 6,603,115; Rhone-Poulenc (1967) Chem. Abstr. 66, 85483.
9. Tsou, D.T., Burrington, J.D., Maher, E.A. and Grasselli, R.K. (1985) Mechanism of rutheniumcatalyzed linear dimerization of acrylonitrile: a kinetic study. J. Mol. Catal. 30, 219-239.
10. Kashiwagi, K., Sugise, R., Shimakawa, T., Matuura, T., Shirai, M., Kakiuchi, F. and Murai, S. (1997) Catalytic dimerization of acrylonitrile. Organometallics 16, 2233-2235.
11. Hong, P., Yamazaki, H., Sonogashira, K. and Hagihara, N. (1978) Rhodium carbonyl cluster catalyzed addition of arenes to diphenylketene and aryl isocyanates. Chem. Lett., 535-538.
12. Jordan, R.F. and Taylor, D.F. (1989) Zirconiumcatalyzed coupling of propene and α-picoline. J. Am. Chem. Soc. 111, 778-779.
13. 2-pyrid-2-yl)+ complexes. J. Am. Chem. Soc. 116, 4491-4492.
14. Moore, E.J., Pretzer, W.R., O'Connel, T.J., Haris, J., LaBounty, L., Chou, L. and Grimmer, S.S. (1992) Catalytic and regioselective acylation of aromatic heterocycles using carbon monoxide and olefins. J. Am. Chem. Soc. 114, 5888-5890.
15. Moore, E.J. and Pretzer, W.R. (1992) Regiospecific carbonylation process for making acyl compounds from aromatic heterocycles and olefins. US Patent, US 5,081,250.
16. Jones, W.D. and Kosar, W.P. (1986) Carbon- hydrogen bond activation by ruthenium for the catalytic synthesis of indoles. J. Am. Chem. Soc. 108, 5640-5641.
17. 2]. Organometallics 13, 385-396.
18. Colquhoun, H.M., Holton, J., Thompson, D.J. and Twigg, M.V. (1984) New Pathways for Organic synthesis. Plenum, New York.
19. Heck, R.F. (1985) Palladium Reagents in Organic Synthesis. Academic Press, London.
20. Fujiwara, Y., Jintoku, T. and Takaki, K. (1990) Look what Pd catalyzes. Chemtech 20, 636-640.
21. Murahashi, S.-I., Naota, T. and Taki, H. (1985) Ruthenium-catalysed oxidation of secondary-amines to imines using tert-butyl hydroperoxide. J. Chem. Soc. Chem. Commun., 613-614.
22. Murahashi, S.-I., Naota, T. and Yonemura, K. (1988) Ruthenium-catalyzed cytochrome-P-450 type oxidation of tertiary-amines with alkyl hydroperoxides. J. Am. Chem. Soc. 110, 8256-8258.
23. Murahashi, S.-I., Naota, T., Kuwabara, T., Saito, T., Kumobayashi, H. and Akutagawa, S. (1990) Ruthenium-catalyzed oxidation of amides and lactams with peroxides. J. Am. Chem. Soc. 112, 7820-7822.
24. Murahashi, S.-I., Saito, T., Naota, T., Kumobayashi, H. and Akutagawa, S. (1991) Ruthenium-catalyzed oxidation of β-lactams with molecular oxygen and aldehydes. Tetrahedron Lett. 32, 5991- 5994.
25. Naota, T., Taki, H., Mizuno, M. and Murahashi, S.-I. (1989) Ruthenium-catalyzed aldol and Michael reactions of activated nitriles. J. Am. Chem. Soc. 111, 5954-5955.
26. Paganelli, S., Schionato, A. and Botteghi, C. (1991) Rhodium-catalyzed Michael additions of activated nitriles to α,β-unsaturated esters. Tetrahedron Lett. 32, 2807-2810.
27. Sawamura, M., Hamashima, H. and Ito, Y. (1992) TRAP-rhodium-catalyzed asymmetric Michael addition of α-cyano carboxylates. J. Am. Chem. Soc. 114, 8295-8296.
28. Yamamoto, Y., Kubota, Y., Honda, Y., Fukui, H., Asao, N. and Nemoto, H. (1994) Transition-metalcatalyzed addition of certain nucleophiles to imines. J. Am. Chem. Soc. 116, 3161-3162.
29. 2 to aldehydes. J. Chem. Soc. Chem. Commun., 1665-1666.
30. Yamamoto, Y., Al-Masum, M. and Asao, N. (1994) Palladium-catalyzed addition of activated methylene and methyne compounds to allenes. J. Am. Chem. Soc. 116, 6019-6020.
31. Murahashi, S.-I., Naota, T., Taki, H., Mizuno, M., Takaya, H., Komiya, S., Mizuho, Y., Oyasato, N., Hiraoka, M., Hirano, M. and Fukuoka, A. (1995) Ruthenium-catalyzed aldol and Michael reactions of nitriles. Carbon-carbon bond formation by,-C-H activation of nitriles. J. Am. Chem. Soc. 117, 12436-12451.
32. Sakai, K., Ide, J., Oda, O. and Nakamura, N. (1972) Synthetic studies on prostanoids 1. Synthesis of methyl 9-oxoprostanoate. Tetrahedron Lett. 13, 1287-1290.
33. Kondo, T., Tsuji, Y. and Watanabe, Y. (1987) Ruthenium complex catalyzed intermolecular hydroacylation of olefins. Tetrahedron Lett. 28, 6229-6230.
34. Marder, T.B., Roe, C. and Milstein, D. (1988) Transition-metal-catalyzed carbon-carbon bond formation via carbon-hydrogen activation. intermolecular hydroacylation: the addition of aldehydes to alkenes. Organometallics 7, 1451-1453.
35. Kondo, T., Akazome, M., Tsuji, Y. and Watanabe, Y. (1990) Ruthenium complex catalyzed intermolecular hydroacylation and transhydroformylation of olefins with aldehydes. J. Org. Chem. 55, 1286- 1291.
36. Watanabe, Y., Mitsudo, T. and Kondo, T. (1992) A new development of ruthenium complex catalysts. Carbon-carbon bond forming reactions. Shokubai 34, 173-181.
37. Watanabe, Y., Mitsudo, T. and Kondo, T. (1992) Chem. Abstr. 117, 191046.
38. Barnhart, R.W., Wang, X., Noheda, P., Bergens, S.H., Whelan, J. and Bosnich, B. (1994) Asymmetric catalysis. Asymmetric catalytic intramolecular hydroacylation of 4-pentenals using chiral rhodium diphosphine catalysts. J. Am. Chem. Soc. 116, 1821-1830.
39. Colquhoun, H.M., Thompson, D.J. and Twigg, M.V. (1991) Decarbonylation. In Carbonylation. Plenum, New York, pp. 205-226.
40. Collman, J.P., Hegedus, L.S., Norton, J.R. and Finke, R.G. (1982) Principles and Applications of Organotransition Metal Chemistry. University Science Books, Mill Valley.
41. Wilkinson, G., Stone, F.G.A. and Abel, E.W. (1982) Comprehensive Organometallic Chemistry. Pergamon, Oxford.
42. For a latest example, Trost, B.M., Romeroand, D.L. and Rise, F. (1994) Palladium-catalyzed cycloisomerization to 1,2-dialkylidenecycloalkanes. 2. Alternative catalyst system. J. Am. Chem. Soc. 116, 4268-4278.
43. Murai, S., Oodan, K., Sugise, R., Shirai, M. and Shimakawa, T. (1994) Preparation of acrylonitrile dimers. Jpn. Kokai Tokkyo Koho JP 06,009,531
44. Murai, S., Oodan, K., Sugise, R., Shirai, M. and Shimakawa, T. (1994) Chem. Abstr. 120, 191146.
45. Murai, S., Kakiuchi, F., Sekine, S., Tanaka, Y., Kamatani, A., Sonoda, M. and Chatani, N. (1993) Efficient catalytic addition of aromatic carbon- hydrogen bonds to olefins. Nature 366, 529-531.
46. Murai, S., Kakiuchi, F., Sekine, S., Tanaka, Y., Kamatani, A., Sonoda, M. and Chatani, N. (1994) Catalytic C-H/olefin coupling. Pure Appl. Chem. 66, 1527-1534.
47. Kakiuchi, F., Sekine, S., Tanaka, Y., Kamatani, A., Sonoda, M., Chatani, N. and Murai, S. (1995) Catalytic addition of aromatic carbon-hydrogen bonds to olefins with the aid of ruthenium complexes. Bull. Chem. Soc. Jpn. 68, 62-83.
48. Sonoda, M., Kakiuchi, F., Chatani, N. and Murai, S. (1995) Directing effect of functional groups in ruthenium-catalyzed addition of substituted acetophenones to an olefin. J. Organomet. Chem. 504, 151-152.
49. Kakiuchi, F., Tanaka, Y., Sato, T., Chatani, N. and Murai, S. (1995) Catalytic addition of olefinic C-H bonds to olefins. Chem. Lett., 679-680.
50. Kakiuchi, F., Yamamoto, Y., Chatani, N. and Murai, S. (1995) Catalytic addition of aromatic C-H bonds to acetylenes. Chem. Lett., 681-682.
51. Sonoda, M., Kakiuchi, F., Kamatani, A., Chatani, N. and Murai, S. (1996) Ruthenium-catalyzed addition of aromatic esters at the ortho C-H bonds to olefins. Chem. Lett., 109-110.
52. Kakiuchi, F., Yamauchi, M., Chatani, N. and Murai, S. (1996) Ruthenium-catalyzed addition of aromatic imines at the ortho C-H bonds to olefins. Chem. Lett., 111-112.
53. Fujii, N., Kakiuchi, F., Chatani, N. and Murai, S. (1996) Transition metal-catalyzed intramolecular C-H/olefin coupling. Chem. Lett., 939-940.
54. Murai, S., Chatani, N. and Kakiuchi, F. (1997) Catalytic addition of C-H bonds to multiple bonds. Pure Appl. Chem. 69, 589-594.
55. Fujii, N., Kakiuchi, F., Yamada, A., Chatani, N. and Murai, S. (1997) Asymmetric intramolecular C-H/olefin coupling: asymmetric cyclization reactions of 1,5-dienes catalyzed by rhodium complexes. Chem. Lett., 425-426.
56. Sonoda, M., Kakiuchi, F., Chatani, N. and Murai, S. (1997) Ruthenium-catalyzed addition of carbon- hydrogen bonds in aromatic ketones to olefins. The effect of various substituents at the aromatic ring. Bull. Chem. Soc. Jpn. 70, 3117-3128.
57. Fujii, N., Kakiuchi, F., Yamada, A., Chatani, N. and Murai, S. (1998) Transition metal-catalyzed intramolecular cyclization of 1,5- and 1,6-dienes via direct cleavage and addition of the carbon-hydrogen bond. Bull. Chem. Soc. Jpn. 71, 285-298.
58. Sato, T., Kakiuchi, F., Chatani, N. and Murai, S. (1998) Ruthenium-catalyzed reactions of acyclic, O-enones with olefins and their reaction mechanisms. Chem. Lett., 893-894.
59. Kakiuchi, F., Sato, T., Tsujimoto, T., Yamauchi, M., Chatani, N. and Murai, S. (1998) New protocol for the siteselective alkylation and vinylation of aromatic compounds. Catalyst-specific reactions. Chem. Lett., 1053-1054.
60. Kakiuchi, F., Sato, T., Yamauchi, M., Chatani, N. and Murai, S. (1999) Ruthenium-catalyzed coupling of aromatic carbon-hydrogen bonds in aromatic imidates with olefins. Chem. Lett., 19-20.
61. Kakiuchi, F., Sonoda, M., Tsujimoto, T., Chatani, N. and Murai, S. (1999) The ruthenium-catalyzed addition of C-H bonds in aromatic nitriles to olefins. Chem. Lett., 1083-1084.
62. Kakiuchi, F., Le Gendre, P., Yamada, A., Ohtaki, H. and Murai, S. (2000) Atropselective alkylation of biaryl compounds by means of transition metal-catalyzed C-H/olefin coupling. Tetrahedron Asymmetry 11, 2647-2651.
63. Kakiuchi, F., Sato, T., Igi, K., Chatani, N. and Murai, S. (2001) The ruthenium-catalyzed addition of β-C-H bonds in aldehydes to olefins. Chem. Lett., 386-387.
64. Kakiuchi, F., Tsujimoto, T., Sonoda, M., Chatani, N. and Murai, S. (2001) The transition metal-catalyzed addition of C-H bonds in aromatic hydrazones to olefins. Synlett, 948-951.
65. 3-catalyzed addition of C-H bonds in aromatic esters to olefins. Chem. Lett., 918-919.
66. Kakiuchi, F., Uetsuhara, T., Tanaka, Y., Chatani, N. and Murai, S. (2002) Ruthenium-catalyzed addition of olefinic C-H bonds in conjugate enones to acetylenes to give conjugate dienones. J. Mol. Catal. Chem. 182-183, 511-514.
67. Hansch, C., Leo, A. and Taft, R.W. (1991) A survey of Hammett substituent constants and resonance and field parameters. Chem. Rev. 91, 165-195.
68. McKinney, R.J., Firestein, G. and Kaesz, H.D. (1975) Metalation of aromatic ketones and anthraquinone with methylmanganese and methylrhenium carbonyl complexes. Inorg. Chem. 14, 2057-2061.
69. Trost, B.M., Imi, K. and Davies, I.W. (1995) Elaboration of conjugated alkenes initiated by insertion into a vinylic C-H bond. J. Am. Chem. Soc. 117, 5371-5372.
70. Marder, T.B., Zargarian, D., Calabrese, J.C., Herskovitz, T.H. and Milstein, D. (1987) C-H rather than O-H activation: synthesis and molecular structure of a cationic cis-hydrido-<-acetylide complex of rhodium. J. Chem. Soc. Chem. Commun., 1484-1485.
71. Bruce, M.I. (1991) Organometallic chemistry of vinylidene and related unsaturated carbenes. Chem. Rev. 91, 197-257.
72. Schore, N.E. (1988) Transition metal-mediated cycloaddition reactions of alkynes in organic synthesis. Chem. Rev. 88, 1081-1119.
73. Wakatsuki, Y. and Yamazaki, H. (1973) Cobaltcatalyzed synthesis of pyridines from acetylenes and nitriles. Tetrahedron Lett. 14, 3383-3384.
74. Trost, B.M., Martinez, J.A., Kulawiec, R.J. and Indolese, A.F. (1993) Ruthenium-catalyzed addition of allyl alcohols and acetylenes. A simple synthesis of γ,δ-unsaturated ketones. J. Am. Chem. Soc. 115, 10402-10403.
75. Naota, T., Takaya, H. and Murahashi, S.-I. (1998) Ruthenium-catalyzed reactions for organic synthesis. Chem. Rev. 98, 2599-2660.
76. 12-catalyzed reactions of pyridylolefins or N-(2-pyridyl)enamines with CO and olefins. Carbonylation at olefinic C-H bonds. J. Org. Chem. 63, 5129-5136.
77. Jun, C.-H., Hong, J.-B., Kim, Y.-H. and Chung, K.-Y. (2000) The catalytic alkylation of aromatic imines by Wilkinson's complex: The domino reaction of hydroacylation and ortho-alkylation. Angew. Chem. Int. Ed. 39, 3440-3442.
78. Ito, T., Horino, H., Koshiro, Y. and Yamamoto, A. (1982) Selective dimerization of aldehyde to esters catalyzed by hydridoruthenium complexes. Bull. Chem. Soc. Jpn. 55, 504-512 and references therein.
79. Tsuji, J. and Ohno, K. (1969) Decarbonylation reaction using transition metal compounds. Synthesis, 157-169.
80. Bosnich, B. (1998) Asymmetric catalysis. A comparative study of the mechanisms of intramolecular hydroacylation and hydrosilation. Acc. Chem. Res. 31, 667-674.
81. Lu, P., Paulasaari, J., Jin, K., Bau, R. and Weber, W.P. (1998) Preparation, characterization, and X-ray structure of the 1:1 complex of o-acetylstyrene and carbonylbis(triphenylphosphine)ruthenium. A new catalyst for the copolymerization of acetophenone and 1,3-divinyltetramethyldisiloxane. Organometallics 17, 584-588.
82. 3) (diphosphine F dppe, dppp, dppb, and dppf). Chem. Lett., 401-402.
83. Singleton, D.A. and Thomas, A.A. (1995) Highprecision simultaneous determination of multiple small kinetic isotope effects at natural abundance. J. Am. Chem. Soc. 117, 9357-9358.
84. 8-organotransition metal complexes. Bull. Chem. Soc. Jpn. 54, 1857-1867.
85. 5(L)Co] moiety. J. Organomet. Chem. 528, 199-203.
86. 6 metallacycle intermediate with agositic interaction. J. Am. Chem. Soc. 120, 12692-12693.
87. Kakiuchi, F., Igi, K., Matsumoto, M., Chatani, N. and Murai, S. (2001) Ruthenium-catalyzed dehydrogenative silylation of aryloxazolines with hydrosilanes via C-H bond cleavage. Chem. Lett., 422-423.
88. Stull, D.R., Westrum, E.F. and Shinke, G.C. (1987) The Chemical Thermodynamics of Organic Compounds. Robert E. Kreiger Publishing, Malabar, FL.
89. Waltz, K.M., He, X., Muhoro, C. and Hartwig, J.F. (1995) Hydrocarbon functionalization by transition metal boryls. J. Am. Chem. Soc. 117, 11357- 11358.
90. Chen, H., Schlecht, S., Semple, T.C. and Hartwig, J.F. (2000) Thermal, catalytic, regiospecific functionalization of alkanes. Science 287, 1995-1997.
91. Kakiuchi, F., Kan, S., Igi, K., Chatani, N. and Murai, S. (2003) A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: a new method for the arylation of aromatic compounds via C-H bond cleavage. J. Am. Chem. Soc. 125, 1698-1699.
92. 12-catalyzed reaction of pyridinylbenzenes with carbon monoxide and olefins. Carbonylation at a C-H bond in the benzene ring. J. Org. Chem. 62, 2604-2610.
93. Murai, S. (1999) Activation of unreactive bonds for organic synthesis. Topic in Organometallic Chemistry Vol. 3 (ed. Murai, S.). Springer, Berlin.
94. Kakiuchi, F. and Murai, S. (1999) Activation of C-H bonds: catalytic reactions. In Topics in Organometallic Chemistry Vol. 3 (ed. Murai, S.). Springer, Berlin, pp. 47-79.
95. Kakiuchi, F. and Chatani, N. (2003) Catalytic methods for C-H bond functionalization: application in organic synthesis. Adv. Synth. Catal. 345, 1077-1101.
96. Kakiuchi, F., Kochi, T., Mizushima, E. and Murai, S. (2010) Room temperature regioselective C-H/olefin coupling of aromatic ketones using an activated ruthenium catalyst with a carbonyl ligand and structural elucidation of key intermediates. J. Am. Chem. Soc. 132, 17741-17750.