Mizoroki-Heck Reactions with Metals Other than Palladium

The Mizoroki-Heck Reaction

Volumn , Issue , 2009, Pages 383-403

  Ackermann, Lutz ^a   Born, Robert ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Catalytic Mizoroki Heck type functionalization reaction of alkenes and palladium; Iridium catalysed Mizoroki Heck type reactions; Mizoroki Heck reactions with metals other than palladium; Nickel catalysed Mizoroki Heck type reactions; Pincer type nickel(II) complex 45; Platinum and iridium based catalysts; Ruthenium catalysed alkenylation of methyl acrylate

Indexed keywords

EID: 84889323392     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470716076.ch10     Document Type: Chapter

References (75)

1. Mizoroki, T., Mori, K. and Ozaki, A. (1971) Arylation of olefin with aryl iodide catalyzed by palladium. Bull. Chem. Soc. Jpn., 44, 581.
2. Heck, R.F. and Nolley, J.P. Jr. (1972) Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J. Org. Chem., 37, 2320.
3. Beller, M. and Bolm, C. (eds) (2004) Transition Metals for Organic Synthesis, 2nd edn, Wiley-VCH Verlag GmbH, Weinheim.
4. De Meijere, A. and Diederich, F. (eds) (2004) Metal-Catalyzed Cross-Coupling Reactions, 2nd edn, Wiley-VCH Verlag GmbH, Weinheim.
5. Beletskaya, I.P. and Cheprakov, A.V. (2000) The Heck reaction as a sharpening stone of palladium catalysis. Chem. Rev., 100, 3009-66.
6. Weissman,H., Song, X. andMilstein,D. (2001) Ru-catalyzed oxidative coupling of arenes with olefins using O2. J. Am. Chem. Soc., 123, 337-8
7. Kakiuchi, F., Sato, T., Yamauchi, M. et al. (1999) Ruthenium-catalyzed coupling of aromatic carbon-hydrogen bonds in aromatic imidates with olefins. Chem. Lett., 28, 19-20.
8. Mori, A., Danda, Y., Fujii, T. et al. (2001) Hydroxorhodium complex-catalyzed carbon-carbon bond-forming reactions of silanediols with α,β-unsaturated carbonyl compounds. Mizoroki-Heck-type reactions vs conjugate addition. J. Am. Chem. Soc., 123, 10774-5.
9. Lautens, M., Roy, A., Fukuoka, K. et al. (2001) Rhodium-catalyzed coupling reactions of arylboronic acids to olefins in aqueous media. J. Am. Chem. Soc., 123, 5358-9.
10. Amengual, R., Michelet, V. and Gen̂et, J.-P. (2002) New studies of Rh-catalyzed addition of boronic acid under basic conditions in aqueous medium. Tetrahedron Lett., 43, 5905-8
11. Martinez, R., Voica, F., Genet, J.-P. and Darses, S. (2007) Base-freeMizoroki-Heck reaction catalyzed by rhodium complexes. Org. Lett., 9, 3213-6.
12. Zou, G., Wang, Z., Zhu, J. and Tang, J. (2003) Rhodium-catalyzed Heck-type reaction of arylboronic acids with α,β-unsaturated esters: tuning β-hydrogen elimination versus hydrolysis of alkylrhodium species. Chem. Commun., 2438-9.
13. Lautens, M., Mancuso, J. and Grover, H. (2004) Rhodium-catalyzed Heck-type coupling of boronic acids with activated alkenes in an aqueous emulsion. Synthesis, 2006-14.
14. De la Herrán, G., Murcia, C. and Csákÿ, A.G. (2005) Rhodium-catalyzed reaction of aryl-and alkenylboronic acids with 2,4-dienoate esters: conjugate addition and Heck reaction products. Org. Lett., 7, 5629-32.
15. Farrington, E.J., Brown, J.M., Barnard, C.F.J. and Rowsell, E. (2002) Ruthenium-catalyzed oxidative Heck reactions. Angew. Chem. Int. Ed., 41, 169-71.
16. Farrington, E.J., Barnard, C.F.J., Rowsell, E. and Brown, J.M. (2005) Ruthenium complexcatalysed Heck reactions of areneboronic acids; mechanism, synthesis and halide tolerance. Adv. Synth. Catal., 347, 185-95.
17. Koike, T., Du, X., Sanada, T. et al. (2003) Iridium-catalyzed Mizoroki-Heck-type reaction of organosilicon reagents. Angew. Chem. Int. Ed., 42, 89-92.
18. Ishiyama, T. and Hartwig, J.F. (2000) A Heck-type reaction involving carbon-heteroatom double bonds. Rhodium(I)-catalyzed coupling of aryl halides with N-pyrazyl aldimines. J. Am. Chem. Soc., 122, 12043-4.
19. Ley, S.V. and Thomas, A.W. (2003) Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation. Angew. Chem. Int. Ed., 42, 5400-49.
20. Kunz, K., Scholz, U. and Ganzer, D. (2003) Renaissance of Ullmann and Goldberg reactions-progress in copper catalyzed C-N-, C-O-and C-S-coupling. Synlett, 2428-39.
21. Iyer, S., Ramesh, C., Sarkar, A. and Wadgaonkar, P.P. (1997) The vinylation of aryl and vinyl halides catalyzed by copper salts. Tetrahedron Lett., 38, 8113-6.
22. Li, J.-H., Wang, D.-P. and Xie, Y.-X. (2005) CuI/Dabco as a highly active catalytic system for the Heck-type reaction. Tetrahedron Lett., 46, 4941-4.
23. Loupy, A. (ed.) (2002) Microwaves in Organic Synthesis,Wiley-VCH Verlag GmbH,Weinheim.
24. Declerck, V., Martinez, J. and Lamaty, F. (2006) Microwave-assisted copper-catalyzed Heck reaction in PEG solvent. Synlett, 3029-32.
25. Yang, Y., Zhou, R., Zhao, S. et al. (2003) Silica-supported poly-γ-aminopropylsilane Ni2+, Cu2+, Co2+ complexes: efficient catalysts for Heck vinylation reaction. J. Mol. Catal. A, 192, 303-6.
26. Iyer, S. and Thakur, V.V. (2000) The novel use of Ni, Co, Cu and Mn heterogenous catalysts for the Heck reaction. J. Mol. Catal. A, 157, 275-8.
27. Yang, Y., Zhou, R., Zhao, S. and Zheng, X. (2003) The vinylation of aryl iodides catalyzed by silica-supported poly-γ-aminopropylsilica Ni, Cu, Co complexes. Catal. Lett., 85, 87-90.
28. Calò, V., Nacci, A., Monopoli, A. et al. (2005) Copper bronze catalyzed Heck reaction in ionic liquids. Org. Lett., 7, 617-20.
29. Lin, B.-L., Liu, L., Fu, Y. et al. (2004) Comparing nickel-and palladium-catalyzed Heck reactions. Organometallics, 23, 2114-23.
30. Chiusoli, G.P., Salerno, G., Giroldini, W. and Pallini, L. (1981) Transition metal-catalyzed synthesis of organic acids by chelation-promoted regioselective double bond insertion. J. Organomet. Chem., 219, C16-20.
31. Colon, I. (1982) Substituted olefins. US Patent 4334081
32. Rollin, Y., Meyer, G., Troupel, M. et al. (1983) Electrocatalytic assistance by nickel complexes of a coupling reaction between alkenes and aromatic halides leading to substituted olefins. J. Chem. Soc., Chem. Commun., 793-4.
33. Boldrini, G.P., Savoia, D., Tagliavini, E. et al. (1986) Nickel-catalyzed coupling of activated alkenes with organic halides. J. Organomet. Chem., 301, C62-4.
34. Lebedev, S.A., Lopatina, V.S., Petrov, E.S. and Beletskaya, I.P. (1988) Condensation of organic bromides with vinyl compounds catalysed by nickel complexes in the presence of zinc. J. Organomet. Chem., 344, 253-9.
35. Sustmann, R., Hopp, P. and Holl, P. (1989) Reactions of organic halides with olefins under Ni(0)-catalysis. Formal addition of hydrocarbons to CC-double bonds. Tetrahedron Lett., 30, 689-92.
36. Kelkar, A.A., Hanaoka, T., Kubota, Y. and Sugi, Y. (1994) The vinylation of bromobiphenyls using homogeneous nickel catalysts. Catal. Lett., 29, 69-75.
37. Ma, S., Wang, H., Gao, K. and Zhao, F. (2006) Nickel complexes catalyzed Heck reaction of iodobenzene and methyl acrylate. J. Mol. Catal. A: Chem., 248, 17-20.
38. Iyer, S., Ramesh, C. and Ramani, A. (1997) Ni(0) catalyzed reactions of aryl and vinyl halides with alkenes and alkynes. Tetrahedron Lett., 38, 8533-6.
39. Inamoto, K., Kuroda, J., Danjo, T. and Sakamoto, T. (2005) Highly efficient nickel-catalyzed Heck reaction using Ni(acac)2/N-heterocyclic carbene catalyst. Synlett, 1624-6.
40. Inamoto, K., Kuroda, J., Hiroya, K. et al. (2006) Synthesis and catalytic activity of a pincer-type bis(imidazolin-2-ylidene) nickel(II) complex. Organometallics, 25, 3095-8.
41. Nakao, Y., Yada, A., Satoh, J. et al. (2006) Arylcyanation of norbornene and norbornadiene catalyzed by nickel. Chem. Lett., 35, 790-1.
42. Bhanage, B.M., Zhao, F.G., Shirai, M. and Arai, M. (1998) Comparison of activity and selectivity of various metal-TPPTS complex catalysts in ethylene glycol-toluene biphasic Heck vinylation reactions of iodobenzene. Tetrahedron Lett., 39, 9509-12.
43. Bhanage, B.M., Zhao, F., Shirai, M. and Arai, M. (1998) Heck reaction using nickel/TPPTS catalyst and inorganic base on supported ethylene glycol phase. Catal. Lett., 54, 195-8.
44. Houdayer, A., Schneider, R., Billaud, D. et al. (2005) New polyaniline/Ni(0) nanocomposites: synthesis, characterization and evaluation of their catalytic activity in Heck couplings. Synth. Met., 151, 165-74.
45. Kelkar, A.A. (1996) The vinylation of aryl iodides using homogeneous platinum complex catalyst. Tetrahedron Lett., 37, 8917-20.
46. Horniakova, J., Nakamura, H., Kawase, R. et al. (2005) Pyridine-derived ruthenium and platinum complexes immobilized on ordered mesoporous silica as catalysts for Heck vinylation. J. Mol. Catal. A, 233, 49-54.
47. Kantam, M.L.,Roy,M., Roy, S. et al. (2006) Layered double hydroxide-supported nanoplatinum: an efficient and reusable ligand-free catalyst for Heck and Stille coupling of iodoarenes. Synlett, 2266-8.
48. Pattenden, G. (1988) Cobalt-mediated radical reactions in organic synthesis. Chem. Soc. Rev., 17, 361-82.
49. Iyer, S. (1995) The vinylation of aryl iodides catalysed by Co,Rh and Ir complexes. J. Organomet. Chem., 490, C27-8.
50. Gomes, P., Gosmini, C., Nédélec, J.-Y. and Périchon, J. (2002) Electrochemical vinylation of aryl and vinyl halides with acrylate esters catalyzed by cobalt bromide. Tetrahedron Lett., 43, 5901-3.
51. Zhou, P., Li, Y., Sun, P. et al. (2007) A novel Heck reaction catalyzed by Co hollow nanospheres in ligand-free condition. Chem. Commun., 1418-20.
52. Terao, J. and Kambe, N. (2001) Titanocene-catalyzed reaction of alkenes and dienes with alkyl halides and chlorosilanes. J. Synth. Org. Chem. Jpn., 59, 1044-51
53. Terao, J., Watabe, H., Miyamoto, M. and Kambe, N. (2003) Titanocene-catalyzed alkylation of aryl-substituted alkenes with alkyl halides. Bull. Chem. Soc. Jpn., 76, 2209-14
54. Terao, J. and Kambe, N. (2006) Transition metal-catalyzed C-C-bond formation reactions using alkyl halides. Bull. Chem. Soc. Jpn., 79, 663-72.
55. Affo,W., Ohmiya,H., Fujioka, T. et al. (2006) Cobalt-catalyzed trimethylsilylmethylmagnesiumpromoted radical alkenylation of alkyl halides: a complement to the Heck reaction. J. Am. Chem. Soc., 128, 8068-77.
56. Branchaud, B.P. and Detlefsen, W.D. (1991) Cobaloxime-catalyzed radical alkyl-styryl crosscouplings. Tetrahedron Lett., 32, 6273-6.
57. Ikeda, Y., Nakamura, T., Yorimitsu, H. and Oshima, K. (2002) Cobalt-catalyzed Heck-type reaction of alkyl halides with styrenes. J. Am. Chem. Soc., 124, 6514-5.
58. Ikeda,Y.,Yorimitsu, H., Shinokubo, H. andOshima, K. (2004) Cobalt-mediated Mizoroki-Hecktype reaction of epoxide with styrene. Adv. Synth. Catal., 346, 1631-4.
59. Fujioka, T., Nakamura, T., Yorimitsu, H. and Oshima, K. (2002) Cobalt-catalyzed intramolecular Heck-type reaction of 6-halo-1-hexene derivatives. Org. Lett., 4, 2257-9.
60. Grigg, R., Stevenson, P. andWorakun, T. (1988) The regioselectivity of rhodium and palladiumcatalysed cyclisations of 2-bromo-1,6-and 1,7-dienes. Tetrahedron, 44, 2033-48.
61. Grigg, R., Sridharan, V., Stevenson, P. et al. (1990) The synthesis of fused ring nitrogen heterocycles via regiospecific intramolecular Heck reactions. Tetrahedron, 46, 4003-18.
62. Sugihara, T., Satoh, T.,Miura,M. and Nomura, M. (2004) Rhodium-catalyzed coupling reaction of aroyl chlorides with alkenes. Adv. Synth. Catal., 346, 1765-72.
63. Sugihara, T., Satoh, T., Miura, M. and Nomura, M. (2003) Rhodium-catalyzed Mizoroki-Hecktype arylation of alkenes with aroyl chlorides under phosphane-and base-free conditions. Angew. Chem. Int. Ed., 42, 4672-4.
64. Dubbaka, S.R. and Vogel, P. (2005) Palladium-catalyzed desulfitative Mizoroki-Heck coupling of sulfonyl chlorideswith mono-and disubstituted olefins: rhodium-catalyzed desulfitative Hecktype reactions under phosphine-and base-free conditions. Chem. Eur. J., 11, 2633-41.
65. Kamigata, N., Ozaki, J.-i., and Kobayashi, M. (1985) Reaction of alkenesulfonyl chlorides with olefins catalyzed by a ruthenium(II) complex. A novel method for synthesis of (E,E)-1,4-diaryl-1,3-butadienes. J. Org. Chem., 50, 5045-50.
66. Mitsudo, T., Takagi, M., Zhang, S.-W., and Watanabe, Y. (1992) Ruthenium complex-catalyzed coupling of vinyl halides with olefins. J. Organomet. Chem., 423, 405-14.
67. Na, Y., Park, S., Han, S.B. et al. (2004) Ruthenium-catalyzed Heck-type olefination and Suzuki coupling reactions: studies on the nature of catalytic species. J. Am. Chem. Soc., 126, 250-8.
68. Oi, S., Sakai, K. and Inoue, Y. (2005) Ruthenium-catalyzed arylation of 2-alkenylpyridines with aryl bromides: alternative E,Z-selectivity to Mizoroki-Heck reaction. Org. Lett., 7, 4009-11.
69. Ackermann, L., Born, R. and Álvarez Bercedo, P. (2007) Ruthenium(IV) alkylidenes as precatalysts for direct arylations of alkenes with aryl chlorides and an application to sequential catalysis. Angew. Chem. Int. Ed., 46, 6364-7.
70. Littke, A.F. and Fu, G.C. (2002) Palladium-catalyzed coupling reactions of aryl chlorides. Angew. Chem. Int. Ed., 41, 4176-211.
71. Ackermann, L. (2005) Phosphine oxides as preligands in ruthenium-catalyzed arylations via C-H-bond functionalization using aryl chlorides. Org. Lett., 7, 3123-5.
72. Campeau, L.-C., Parisien, M., Jean, A. and Fagnou, K. (2006) Catalytic direct arylation with aryl chlorides, bromides, and iodides: intramolecular studies leading to new intermolecular reactions. J. Am. Chem. Soc., 128, 581-90.
73. Lafrance, M., Rowley, C.N., Woo, T.K. and Fagnou, K. (2006) Catalytic intermolecular direct arylation of perfluorobenzenes. J. Am. Chem. Soc., 128, 8754-6.
74. Chiong, H.A. and Daugulis, O. (2007) Palladium-catalyzed arylation of electron-rich heterocycles with aryl chlorides. Org. Lett., 9, 1449-51.
75. Littke, A.F. and Fu, G.C. (2001) A versatile catalyst for Heck reactions of aryl chlorides and aryl bromides under mild conditions. J. Am. Chem. Soc., 123, 6989-7000.