Direct synthesis of alkylsilanes by platinum-catalyzed coupling of hydrosilanes and iodoalkanes

Chemical Communications

Volumn 49, Issue 2, 2013, Pages 134-136

  Inubushi, Hikaru ^a   Kondo, Hitoshi ^a   Lesbani, Aldes ^a   Miyachi, Mariko ^a   Yamanoi, Yoshinori ^a   Nishihara, Hiroshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; ALKYL GROUP; FUNCTIONAL GROUP; INSECTICIDE; IODINE DERIVATIVE; PLATINUM; SILAFLUOFEN; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; QUANTUM YIELD; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

EID: 84870488994     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc35150a     Document Type: Article

References (52)

1. S. M. Sieburth, Isosteric Replacement of Carbon with Silicon in the Design of Safer Chemicals, in Designing Safer Chemicals, ed. S. C. DeVito and R. L. Garrett, American Chemical Society, Washington, DC, 1996, pp. 74-83.
2. R. Tacke, H. Linoh, S. Patai and Z. Rappoport, Bioorganosilicon Chemistry, in The Chemistry of Organic Silicon Compounds, John Wiley & Sons, New York, vol. 2, 1989, pp. 1143-1206.
3. S. Barcza, The Value and New Directions of Silicon Chemistry for Obtaining Bioactive Compounds, in Silicon Chemistry, ed. E. R. Corey, J. Y. Corey and P. P. Gasper, Wiley, New York, 1988, pp. 135-144.
4. W. K. Moberb, G. S. Basarab, J. Cuomo, P. H. Liang and R. Greenhalgh, T. R. Roberts, Biologically Active Organosilane Compounds: Silicon-Containing Triazole Fungicides, in Pesticide Science and Biotechnology, Blackwell Scientific, Boston, 1986, pp. 57-60
5. S. M. Sieburth, C. J. Manly Pestic. Sci. 1990 28 289.
6. FMC Corporation, US Patent, 4709068, 1987.
7. Y. Katsuda, Y. Minamite, C. Vongkalung Insects 2011 2 532.
8. N. A. Rizvi, J. L. Marshall J. Clin. Oncol. 2002 20 3522.
9. P. Kocsis, S. J. Farkas J. Pharmacol. Exp. Ther. 2005 315 1237.
10. The Chemistry of Organic Silicon Compounds, ed. S. Patai and Z. Rappoport, Wiley, New York, 1989, vol. 1.
11. The Chemistry of Organic Silicon Compounds, ed. Z. Rappoport and Y. Apeloig, Wiley, New York, 1998, vol. 2.
12. Comprehensive Handbook of Hydrosilylation, ed. B. Marciniec, Pergamon Press, Oxford, 1992.
13. A. Kunai, T. Sakurai, E. Toyoda, M. Ishikawa, Y. Yamamoto Organometallics 1994 13 32-33.
14. R. Boukherroub, C. Chatgilialoglu, G. Manuel Organometallics 1996 15 1508.
15. A. Iwata, Y. Toyoshima, T. Hayashida, T. Ochi, A. Kunai, J. Ohshita J. Organomet. Chem. 2003 667 90.
16. A. Kunai, J. Ohshita J. Organomet. Chem. 2003 686 3.
17. J. Ohshita, R. Taketsugu, Y. Nakahara, A. Kunai J. Organomet. Chem. 2004 689 3258.
18. P. Srithanakit, W. Chavasiri Tetrahedron Lett. 2011 52 2505.
19. K. Miura, M. Tomita, Y. Yamada, A. Hosomi J. Org. Chem. 2007 72 787.
20. Y. Yamanoi J. Org. Chem. 2005 70 9607.
21. Y. Yamanoi, H. Nishihara Tetrahedron Lett. 2006 47 7157.
22. Y. Yamanoi, H. Nishihara J. Org. Chem. 2008 73 6671.
23. Y. Yamanoi, T. Taira, J. Sato, I. Nakamula, H. Nishihara Org. Lett. 2007 9 4543.
24. Y. Yamanoi, H. Nishihara J. Synth. Org. Chem. Jpn. 2009 67 778.
25. Y. Yabusaki, N. Ohshima, H. Kondo, T. Kusamoto, Y. Yamanoi, H. Nishihara Chem.-Eur. J. 2010 16 55-81.
26. A. Lesbani, H. Kondo, J. Sato, Y. Yamanoi, H. Nishihara Chem. Commun. 2010 46 77-84.
27. A. Lesbani, H. Kondo, Y. Yabusaki, M. Nakai, Y. Yamanoi, H. Nishihara Chem.-Eur. J. 2010 16 13519.
28. M. Murata, Y. Masuda J. Synth. Org. Chem. Jpn. 2010 68 845.
29. C. Huang, N. Chernyak, A. S. Dudnik, V. Gevorgyan Adv. Synth. Catal. 2011 353 1285.
30. N. Iranpoor, H. Firouzabadi, R. J. Azadi J. Organomet. Chem. 2010 695 887.
31. M. Iizuka, Y. Kondo Eur. J. Org. Chem. 2008 1161.
32. M. Murata, H. Ohara, R. Oiwa, S. Watanabe, Y. Masuda Synthesis 2006 1771.
33. D. Karshtedt, A. T. Bell, T. D. Tilley Organometallics 2006 25 4471.
34. A. Ochida, S. Ito, T. Miyahara, H. Ito, M. Sawamura Chem. Lett. 2006 294.
35. W. Gu, S. Liu, R. B. Silverman Org. Lett. 2002 4 4171.
36. M. Murata, S. Watanabe, Y. Masuda Tetrahedron Lett. 1999 40 9255.
37. J. Bergueiro, J. Montenegro, F. Cambeiro, C. Saá, S. López Chem.-Eur. J. 2012 18 4401.
38. M. Ciriano, M. Green, J. A. K. Howard, J. Proud, J. Spencer, F. G. A. Stone, C. A. Tsipis J. Chem. Soc., Dalton Trans. 1978 801.
39. L. A. Latif, C. Eaborn, A. P. Pidcock, N. S. Weng J. Organomet. Chem. 1994 474 217.
40. D. F. Mullica, E. L. Sappenfield, M. L. Hampden-Smith Polyhedron 1991 10 867.
41. T. Koizumi, K. Osakada, T. Yamamoto Organometallics 1997 16 6014.
42. J. Voigt, T. Braum Dalton Trans. 2011 40 12699.
43. J. Zhou, G. C. Fu J. Am. Chem. Soc. 2003 125 12527.
44. Y. Yang, X. Huang Synth. Commun. 1997 27 345.
45. S. Al-Ahmad, H. Hudali, M. H. Zaghal Inorg. Chim. Acta 1988 147 1.
46. A. Hamze, O. Provot, M. Alami, J.-D. Brion Org. Lett. 2006 8 931.
47. Y. Song, C.-I. Liu, F.-Y. Lin, J. H. No, M. Hensler, Y.-L. Liu, W.-Y. Jeng, J. Low, G. Y. Liu, V. Nizet, A. H.-J. Wang, E. Oldfield J. Med. Chem. 2009 52 3869.
48. R. G. Goel, W. O. Ogini, R. C. Srivastava J. Organomet. Chem. 1981 214 405.
49. M. A. Bennett, S. K. Bhargava, M. Ke, A. C. Willis Dalton Trans. 2000 3537.
50. T. G. Appleton, H. C. Clark, L. E. Manzer J. Organomet. Chem. 1974 65 275.
51. A. J. Canty, R. P. Watson, S. S. Karpiniec, T. Rodemann, M. G. Gardiner, R. C. Jones Organometallics 2008 27 3203.
52. R. N. Perutz, S. Sabo-Etienne Angew. Chem., Int. Ed. 2007 46 2578.