Taylor-made palladium-pincer complexes: A new source of more efficient catalysts for sustainable organic synthesis

Inorganica Chimica Acta

Volumn 363, Issue 9, 2010, Pages 1903-1911

  Moreno, Isabel ^a   SanMartin, Raul ^a   Inés, Blanca ^a   Churruca, Fátima ^a   Domínguez, Esther ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Catalysis; Cross coupling; Palladium; Pincer; Sustainable protocols

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; PALLADIUM; PALLADIUM COMPOUNDS;

CATALYTIC SYSTEM; CROSS-COUPLINGS; EFFICIENT CATALYSTS; ORGANIC SYNTHESIS; PALLADACYCLES; PALLADIUM COMPLEXES; PALLADIUM PINCER-COMPLEXES; PINCER;

SYNTHESIS (CHEMICAL);

EID: 77953321076     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2009.03.003     Document Type: Review

References (87)

1. For a revision on the use of pincer complexes in organic synthesis, see:. Singleton J.T. Tetrahedron 59 (2003) 1837
2. For some examples related with the immobilization of pincer palladacycles onto heterogeneous and/or polymer support see:. Bergbreiter D.E., Osburn P.L., and Frels J. J. Am. Chem. Soc. 123 (2001) 11105
3. Chanthateyanonth R., and Alper H. Adv. Synth. Catal. 346 (2004) 1375
4. Rietveld M.H.P., Grove D.M., and van Koten G. New J. Chem. 21 (1997) 751
5. Dijkstra H.P., Slag M.Q., McDonald A., Kruthof C.A., Kreiter R., Mills A.M., Lutz M., Spek A.L., Klopper W., van Klink G.P.M., and van Koten G. Eur. J. Inorg. Chem. (2003) 830
6. Slagt M.Q., van Zwieten D.A.P., Moerkerk A.J.C.M., Gebbink R.J.M.K., and van Koten G. Coord. Chem. Rev. 248 (2004) 2275
7. The application of such NCN-palladacycles in cross-coupling reactions is described in:. Magill A.M., McGuines D.S., Cavell K.J., Britovsek G.J.P., Gibson V.C., White A.J.P., Williams D.J., and White A.M. J. Organomet. Chem. 617-618 (2001) 546
8. Jung I.G., Son S.U., Park K.H., Chung K.-C., Lee J.W., and Chung Y.K. Organometallics 22 (2003) 4715
9. Díez-Barra E., Guerra J., Hornillos V., Merino S., and Tejeda J. Organometallics 22 (2003) 4610
10. Gupta A.K., Rim C.Y., and Oh C.H. Synlett (2004) 2227
11. Takenaka K., Minakawa M., and Uozomi Y. J. Am. Chem. Soc. 127 (2005) 12273
12. Soro B., Stoccoro S., Minghetti G., Zucca A., Cinellu M.A., Gladiali S., Manassero M., and Sansoni M. Organometallics 24 (2005) 53
13. Soro B., Stocorro S., Minghetti G., Zucca A., Cinellu M.A., Manassero M., and Gladiali S. Inorg. Chim. Acta 359 (2006) 1879
14. Churruca F., SanMartin R., Tellitu I., and Domínguez E. Synlett (2005) 3116
15. Hartshorn C., and Steel P.J. Organometallics 17 (1998) 4387
16. For the seminal works on this subject, see:. Heck R.F., and Nolley J.P. J. Org. Chem. 37 (1972) 2320
17. Mizoroki T., Mori K., and Ozaki A. Bull. Chem. Soc. Jpn. 44 (1971) 581
18. For a review on Suzuki coupling see:. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
19. Suzuki A. J. Organomet. Chem. 576 (1999) 147
20. For a seminal work see:. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. 16 (1975) 4467
21. Eberhard M.R., Wang Z., and Jensen C.M. Chem. Commun. (2002) 818
22. Loch J.A., Albrech M., Peris E., Mata J., Faller J., and Crabtree R.H. Organometallics 21 (2002) 700
23. Mas-Marzá E., Segarra A.M., Claver C., Perisb E., and Fernández E. Tetrahedron Lett. 44 (2003) 6595
24. Luo Q., Eibauer S., and Reiser O. J. Mol. Catal. A: Chem. 268 (2007) 65
25. Although mechanistic studies suggest that metallic palladium(0) plays a significant role in the catalysis, the participation as catalyst of the pincer complexes is not completely excluded:. Eberhard M.R. Org. Lett. 6 (2004) 2125
26. Sommer W.J., Yu K.Q., Sears J.S., Ji Y.Y., Zheng X.L., Davis R.J., Sherrill C.D., Jones C.W., and Weck M. Organometallics 24 (2005) 4351
27. Ohff M., Ohff A., van der Boom E., and Milstein D. J. Am. Chem. Soc. 119 (1997) 11687
28. Morales-Morales D., Cramer R.E., and Jensen C.M. J. Organomet. Chem. 654 (2002) 44
29. Olsson D., Nilsson P., El Masnaouy M., and Wendt O.F. Dalton Trans. (2005) 1924
30. For a review about phosphine-based pincer complexes see:. van der Boom M.E., and Milstein D. Chem. Rev. 103 (2003) 1759
31. Miyazaki F., Yamaguchi K., and Shibsaki M. Tetrahedron Lett. 40 (1999) 7379
32. Bedford R.B., Draper S.M., Scully P.N., and Welch S.L. New J. Chem. 24 (2000) 745
33. Morales-Morales D., Grause C., Kasaoka K., Redón R., Cramer R.E., and Jensen C.M. Inorg. Chim. Acta 300-302 (2000) 958
34. Morales-Morales D., Redón R., Yung C., and Jensen C.M. Chem. Commun. (2000) 1619 See also Ref. [10]
35. Naghipour A., Sabounchei S.J., Morales-Morales D., Hernández-Ortega S., and Jensen C.M. J. Organomet. Chem. 689 (2004) 2494
36. Beller M., and Zapf A. Synlett (1998) 792
37. Churruca F., SanMartín R., Tellitu I., and Domínguez E. Tetrahedron Lett. 47 (2006) 3233
38. PCP palladium pincer complexes have been used in allylic alkylation:. Wang Z., Eberhard M.R., Jensen C.M., Matsukawa S., and Yamamoto Y. J. Organomet. Chem. 681 (2003) 185
39. Allylic stannylation:. Wallner O.A., and Szabó K. Org. Lett. 6 (2004) 1829
40. Allylation of aldehydes and imines:. Solin N., Walner O.A., and Szabó K.J. Org. Lett. 7 (2005) 689
41. Churruca F., SanMartin R., Tellitu I., and Domínguez E. Org. Lett. 4 (2002) 1591
42. Churruca F., SanMartin R., Tellitu I., and Domínguez E. Tetrahedron Lett. 44 (2003) 5925
43. Churruca F., SanMartin R., Carril M., Tellitu I., and Domínguez E. Tetrahedron 60 (2004) 2393
44. Carril M., SanMartin R., Tellitu I., and Domínguez E. Org. Lett. 7 (2005) 4787
45. Ogo S., Takebe Y., Uehara K., Yamazaki T., Nakai H., Watanabe Y., and Fukuzumi S.S. Organometallics 25 (2006) 331
46. Benito-Garagorri D., Bocokic V., Mereiter K., and Kirchner K. Organometallics 25 (2006) 3817
47. Other recent works regarding the synthesis and employment of PCP pincer ligands are described in:. Kimura T., and Uozomi Y. Organometallics 25 (2006) 4883
48. Gong J.-F., Zhang Y.-H., Song M.-P., and Xu C. Organometallics 26 (2007) 6487
49. Naghipour A., Sabounchei S.J., Morales-Morales D., Canseco-González D., and Jensen C.M. Polyhedron 26 (2007) 1445
50. Neo K.E., Huynh H.V., Koh L.L., Henderson W., and Hor T.S.A. J. Organomet. Chem. 693 (2008) 1628
51. Bolliger J.L., Blacque O., and Frech C.M. Chem. Eur. J. 14 (2008) 7969
52. Peris E., Loch J.A., Mata J., and Crabtree R.H. Chem. Commun. (2001) 201
53. A revision about the catalytic applications of N-heterocyclic carbenes in:. Peris E., and Crabtree R.H. Coord. Chem. Rev. 248 (2004) 2239
54. Gründermann S., Albrecht M., Loch J.A., Faller J.W., and Crabtree R.H. Organometallics 20 (2001) 5485
55. The incorporation of aryl substituents in the imidazole rings does not improve the catalytic activity of this type of complexes in Heck reaction:. Tulloch A.A.D., Danopoulos A.A., Tizzard G.J., Coles S.J., Hursthouse M.B., Hay-Motherwell R.S., and Motherwell W.B. Chem. Commun. (2001) 1270
56. Ekkehardt F., Jahnke M.C., Gomez-Benítez V., Morales-Morales D., and Pape T. Organometallics 24 (2005) 6458
57. Poyatos M., Márquez F., Peris E., Claver C., and Fernández E. New J. Chem. 27 (2003) 425
58. Steel P.G., and Teasdale C.W.T. Tetrahedron Lett. 45 (2004) 8977
59. Churruca F., SanMartin R., Inés B., Tellitu I., and Domínguez E. Adv. Synth. Catal. 348 (2006) 1836
60. Wei W., Qin Y., Luo M., Xia P., and Wong M.S. Organometallics 27 (2008) 2268
61. Tu T., Malineli J., and Dötz K.H. Adv. Synth. Catal. 350 (2008) 1791
62. For other unsymmetrical pincer complexes employed as catalysts in cross-coupling reactions see:. Bravo J., Cativiela C., Navarro R., and Urriolabeitia E.P. J. Organomet. Chem. 650 (2002) 157
63. Chen C.-T., Chan Y.-S., Tzeng Y.-R., and Chen M.-T. Dalton Trans. (2004) 2691
64. Bianchini C., Lenoble G., Oberhauser W., Parisel S., and Zanobini M. Eur. J. Inorg. Chem. (2005) 4794
65. Chen M.-T., Huang C.-A., and Chen C.-T. Eur. J. Inorg. Chem. (2006) 4642
66. Debono N., Iglesias M., and Sánchez F. Adv. Synth. Catal. 349 (2007) 2370
67. Bröring M., Kleeberg C., and Köhler S. Inorg. Chem. 47 (2008) 6404
68. PCN pincer complexes have been used as catalysts in other reactions. See for example:. Motoyama Y., Shimozono K., and Nishiyama H. Inorg. Chim. Acta 359 (2006) 1725
69. Rosa R.G., Ebeling G., Dupont J., and Monteiro A.L. Synthesis (2003) 2894
70. Consorti C.S., Ebeling G., Flores F.R., Rominger F., and Dupont J. Adv. Synth. Catal. 346 (2004) 617
71. Rosa G.R., Rosa C.H., Rominger F.R., Dupont J., and Monteiro A.L. Inorg. Chim. Acta 359 (2006) 1947
72. Inés B., SanMartín R., Churruca F., Domínguez E., Urtiaga M.K., and Arriortua M.I. Organometallics 27 (2008) 2833
73. For more details about the synthesis and characterization of complex 12, included crystallographic data see Ref. [26].
74. Hatanaka Y., and Hiyama T.J. Org. Chem. 53 (1988) 918
75. Although in his pioneering report Hiyama claimed the need of fluoride ions to facilitate the transmetallation step, later it has been demonstrated that this process can be similarly promoted by sodium hydroxide:. Handy C.J., Manoso A.S., McEroy W.T., Seganish W.M., and DeShong P. Tetrahedron 61 (2005) 12201
76. Gordillo A., de Jesús E., and López-Mardomingo C. Org. Lett. 8 (2006) 3517
77. The addition of fluoride ion or the use of organic solvents did not get better results. For more details see Ref. [26].
78. Inés B., Moreno I., Sanmartín R., and Domínguez E. J. Org. Chem. 73 (2008) 8448
79. Kondolff I., Doucet H., and Santelli M. Tetrahedron 60 (2004) 3813
80. Palladium catalyzed cross-coupling of α-haloenones with arylboronic acids have been scarcely studied. See for example:. Felpin F.-X. J. Org. Chem. 70 (2005) 8575
81. Banks J.C., Van Mele D., and Frost C.G. Tetrahedron Lett. 47 (2006) 2863
82. Burns M.J., Fairlamb J.S., Kapdi A.R., Sehnal P., and Taylor R.J.K. Org. Lett. 9 (2007) 5397
83. Dawood K.M. Tetrahedron 63 (2007) 9642
84. For the use of a NCN symmetric pincer in a Suzuki coupling with one benzyl derivative see Ref. [13].
85. For a recent review on palladium-catalyzed functionalization of benzylic derivatives, see:. Liégault B., Renaud J.-L., and Bruneau C. Chem. Soc. Rev. 37 (2008) 290
86. All of our efforts to accomplishing the reaction in neat water were unsuccessful and in all cases the starting materials were recovered.
87. A PCP palladium pincer has been used in a Suzuki coupling with bromoundecane as electrophilic partner. See Ref. [25].