Hydrosilylation of internal alkynes catalyzed by tris- Imidazolium salt-Stabilized palladium nanoparticles

Advanced Synthesis and Catalysis

Volumn 356, Issue 1, 2014, Pages 179-188

  Planellas, Marc ^a   Guo, Wusheng ^a   Alonso, Francisco ^a   Yus, Miguel ^b   Shafir, Alexandr ^a   Pleixats, Roser ^a   Parella, Teodor ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^b UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Alkynes; hydrosilylation; Imidazolium salts; Nanoparticles; Palladium; Transfer hydrogenation

Indexed keywords

EID: 84893976095     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201300641     Document Type: Article

References (63)

1. a) I. Ojima, Z. Li, J. Zhu, in: The Chemistry of Organo-silicon Compounds; (Eds.: Z. Rappoport, Y. Apeloig), Wiley-VCH, Weinheim, 1998, Vol. 2, pp 1687-1792;
2. b) B. Marciniec; H. Maciejewski, C. Pietraszuk, P. Pawluc, in: Hydrosilylation: A Comprehensive Review on Recent Advances, Advances in Silicon Science Series, (Ed.: B. Marciniec), Springer Verlag, Berlin, Heidelberg, 2009, Vol. 1, Chapter 2.
3. B. M. Trost, Z. T. Ball, T. Jçge, J. Am. Chem. Soc. 2002, 124, 7922-7923.
4. For some recent reviews on the palladium-catalyzed cross-coupling of organosilicon reagents, see: a) Y. Nakao, T. Hiyama, Chem. Soc. Rev. 2011, 40, 4893-4901;
5. b) H. F. Sore, W. R. J. D. Galloway, D. R. Spring, Chem. Soc. Rev. 2012, 41, 1845-1866.
6. a) K. Tamao, N. Ishida, T. Tanaka, M. Kumada, Orga-nometallics 1983, 2, 1694-1696;
7. b) I. Fleming, R. Hen-ning, H. Plaut, J. Chem. Soc. Chem. Commun. 1984, 29-31.
8. a) J. L. Speier, J. A. Webster, H. H. Barnes, J. Am. Chem. Soc. 1957, 79, 974-979;
9. b) G. Chandra, P. Y Lo, P. B. Hitchcock, M. F Lappert, Organometallics 1987, 6, 191-192;
10. c) B. D. Karstedt, U.S. Patent 3,775,452, 1973;
11. d) J. Stein, L. N. Lewis, Y Gao, R. A. Scott, J. Am. Chem. Soc. 1999,121, 3693-3703.
12. For the early work, see: a) M. A. Esteruelas, J. Herrero, L. A. Oro, Organometallics 1993, 12, 2377-2379.
13. For later work, see: b) Y Na, S. Chang, Org. Lett. 2000, 2, 1887-1889;
14. c) S. V Maifeld, M. T. Tran, D. Lee, Tetrahedron Lett. 2005, 46, 105-108;
15. d) C. Menozzi, PI. Dalko, J. Cossy, J. Org. Chem. 2005, 70, 10717-10719;
16. e) C. S. Aricó, L. R. Cox, Org. Biomol. Chem. 2004, 2, 2558-2562;
17. f) B. M. Trost, Z. T. Ball, J. Am. Chem. Soc. 2001, 123, 12726-12727;
18. g) B. M. Trost, Z. T Ball, J. Am. Chem. Soc. 2005,127, 17644-17655.
19. a) W A. Solomonsz, G. A. Rance, M. Suyetin, A. La Torre, E. Bichoutskaia, A. N. Khlobystov, Chem. Eur. J. 2012, 18, 13180-13187;
20. b) A. Psyllaki, I. N. Lykakis, M. Stratakis, Tetrahedron 2012, 68, 8724-8731.
21. a) F. Alonso, R. Buitrago, Y. Moglie, J. Ruiz-Martinez, A. Sepffllveda-Escribano, M. Yus, J. Organomet. Chem. 2011, 696, 368-372;
22. b) F. Alonso, R. Buitrago, Y. Moglie, A. Sepffllveda-Escribano, M. Yus, Organometallics 2012, 31, 2336-2342;
23. c) R. Cano, M. Yus, D. J. Ramon, ACS Catal. 2012, 2,1070-1078.
24. a) A. Roucoux, J. Schulz, H. Patin, Chem. Rev. 2002, 102, 3757-3778;
25. b) M. Moreno-Mañas, R. Pleixats, Acc. Chem. Res. 2003, 36, 638-643;
26. c) A. Balanta, C. Godard, C. Claver, Chem. Soc. Rev. 2011, 40, 4973-4985;
27. d) Nanoparticles and Catalysis, (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2008.
28. M. Benohoud, S. Tuokko, P. M. Pihko, Chem. Eur. J. 2011.17, 8404-8413.
29. M. Tamura, H. Fujihara, J. Am. Chem. Soc. 2003, 125, 15742-15743.
30. a) D. Motoda, H. Shinokubo, K. Oshima, Synlett 2002, 1529-1531;
31. b) Y Sumida, T Kato, S. Yoshida, T Hosoya, Org. Lett. 2012, 14, 1552-1555;
32. c) H. Zhou, C. Moberg, Org. Lett. 2013,15, 1444-1447.
33. M. Planellas, R. Pleixats, A. Shafir, Adv. Synth. Catal. 2012, 354, 651-662.
34. K. Philippot, B. Chaudret, Organometallic Derived Metals, Colloids and Nanop articles, in: Comprehensive Organometallic Chemistry III, (Eds.: R. H. Crabtree, M. P. Mingos), Elsevier, 2007, Vol. 12, Chapter 12-03, pp 71-99.
35. a) M. F. Rettig, P. M. Maitlis, Inorg. Synth. 1990, 28, 110-113.
36. D. A. Rooke, E. M. Ferreira, Angew. Chem. 2012, 124, 3279-3284;
37. Angew. Chem. Int. Ed. 2012, 51, 3225-3230.
38. S. Gil, J. F. Espinosa, T Parella, J. Magn. Reson. 2011, 213, 145-150.
39. a) T Mitsudome, S. Arita, H. Mori, T Mizugaki, K. Jit-sukawa, K. Kaneda, Angew. Chem. 2008, 120, 8056-8058;
40. Angew. Chem. Int. Ed. 2008, 47, 7938-7940;
41. b) T Mitsudome, A. Noujima, T Mizugaki, K. Jitsukawa, K. Kaneda, Chem. Commun. 2009, 5302-5304;
42. c) N. Asao, Y Ishikawa, N. Hatakeyama, Menggenbateer, Y Ya-mamoto, M. Chen, W Zhang, A. Inoue, Angew. Chem. 2010, 122, 10291-10293;
43. Angew. Chem. Int. Ed. 2010, 49, 10093-10095;
44. d) W Li, A. Wang, X. Yang, Y Huang, T Zhang, Chem. Commun. 2012, 48, 9183-9185;
45. e) M. Yan, T Jin, Y Ishikawa, T Minato, T Fujita, L.-Y Chen, M. Bao, N. Asao, M.-W Chen, Y Yamamoto, J. Am. Chem. Soc. 2012, 134, 17536-17542;
46. f) K. Shimizu, T Kubo, A. Satsuma, Chem. Eur. J. 2012.18, 2226-2229;
47. g) M. Jeon, J. Han, J. Park, Chem-CatChem 2012, 4, 521-524;
48. h) K. Shimizu, K. Shimura, N. Imaiida, A. Satsuma, J. Mol. Catal. A: Chem. 2012, 365, 50-54;
49. i) E. A. Ison, R. A. Corbin, M. M. Abu-Omar, J. Am. Chem. Soc. 2005,127, 11938-11939;
50. j) Y Lee, D. Seomoon, S. Kim, H. Han, S. Chang, P. H. Lee, J. Org. Chem. 2004, 69, 1741-1743;
51. k) D.-W Wang, D-Sh. Wang, Q.-A. Chen, Y.-G Zhou, Chem. Eur. J. 2010, 16, 1133-1136;
52. l) M. Lee, S. Ko, S. Chang, J. Am. Chem. Soc. 2000, 122, 12011-12012;
53. m) E. Choi, C. Lee, Y Na, S. Chang, Org. Lett. 2002, 4, 2369-2371;
54. n) K. Mori, M. Tano, T Mizugaki, K. Ebitani, K. Kaneda, New. J. Chem. 2002, 26, 1536-1538;
55. o) S. T Tan, J. W Kee, W Y Fan, Organometallics 2011, 30, 4008-4013;
56. p) W Sattler, G Parkin, J. Am. Chem. Soc. 2012, 134, 17462-17465;
57. q) M. Jeon, J. Han, J. Park, ACS Catal. 2012, 2,1539-1549.
58. J. M. Tour, J. P. Cooper, S. L. Pendalwar, J. Org. Chem. 1990, 55, 3452-3453.
59. I. N. Lykakis, A. Psyllaki, M. Stratakis, J. Am. Chem. Soc. 2011, 133, 10426-10429.
60. C. Gryparis, M. Stratakis, Chem. Commun. 2012, 48, 10751-10753.
61. A. M. Whittaker, G. Lalic, Org. Lett. 2013, 15, 1112-1115.
62. P. K. Mandal, J. S. McMurray, J. Org. Chem. 2007, 72, 6599-6601.
63. Formation of HD from a mixture of Et3SiH, D2O and 1b-Pd in C6D6 at 333 K was detected by 1H NMR as a 1:1:1 signal at 4.43 ppm (JHD = 42.7 Hz) (see the Supporting Information). The chemical shift and coupling constant are in agreement with the reported values for HD in toluene-d8, see: J. Y.-C. Chen, A. A. Marti, N. J. Turro, K. Komatsu, Y. Murata, R. G. Lawler, J. Phys. Chem. B 2010,114,14689-14695.