Facile, high-yield functionalization of germanium and tin by oxidative insertion of tetrelenes into the E-H bonds of inorganic acids (E = C, N, O, F): Arene elimination versus oxidative addition and formation of a germanium cation-water complex

Organometallics

Volumn 32, Issue 2, 2013, Pages 617-622

  Brown, Zachary D ^a   Erickson, Jeremy D ^a   Fettinger, James C ^a   Power, Philip P ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON SPECIES; FUNCTIONALIZATIONS; GERMYLENES; OXIDATIVE ADDITIONS; OXIDATIVE INSERTION; STANNYLENES; TRACE AMOUNTS; TRIFLIC ACIDS;

HYDROGEN; INORGANIC ACIDS; TIN;

GERMANIUM;

EID: 84872910682     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om301121x     Document Type: Article

References (60)

1. Martin, D.; Soleilhavoup, M.; Bertrand, G. Chem. Sci. 2011, 2, 389-399
2. Arduengo, A. J., III. Acc. Chem. Res. 2011, 32, 913-921
3. Lappert, M. F. J. Organomet. Chem. 2005, 690, 5467-5473
4. Power, P. P. Acc. Chem. Res. 2011, 44, 627-637
5. Power, P. P. Nature 2010, 463, 171-177
6. Al-Rafia, S. M. I.; Malcolm, A. C.; McDonald, R.; Ferguson, M. J.; Rivard, E. Angew. Chem., Int. Ed. 2011, 50, 8354-8357
7. Sekiguchi, A.; Kinjo, R.; Ichinohe, M. Science 2004, 305, 1755
8. Stender, M.; Phillips, A. D.; Wright, R. J.; Power, P. P. Angew. Chem., Int. Ed. 2002, 41, 1785-1787
9. Phillips, A. D.; Wright, R. J.; Olmstead, M. M.; Power, P. P. J. Am. Chem. Soc. 2002, 124, 5930-5931
10. Pu, L.; Twamley, B.; Power, P. P. J. Am. Chem. Soc. 2000, 122, 3524-3525
11. Yao, S.; Xiong, Y.; Driess, M. Chem.-Eur. J. 2010, 16, 1281-1288
12. Li, L.; Fukawa, T.; Matsuo, T.; Hashizume, D.; Fueno, H.; Tanaka, K.; Tameo, K. Nat. Chem. 2012, 4, 361-365.
13. Spikes, G. H.; Fettinger, J. C.; Power, P. P. J. Am. Chem. Soc. 2005, 127, 12232-12233
14. Welch, G. C.; San Juan, R. R.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124-1126
15. Geier, S. J.; Gilbert, T. M.; Stephan, D. W. J. Am. Chem. Soc. 2008, 130, 12632-12633
16. Ullrich, M.; Lough, A. J.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 52-53
17. Frey, G. D.; Lavallo, V.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. Science 2007, 316, 439-441
18. Jana, A.; Schulzke, C.; Roesky, H. W. J. Am. Chem. Soc. 2009, 131, 4600-4601
19. Xiong, Y.; Yao, S.; Müller, R.; Kaupp, M.; Driess, M. J. Am. Chem. Soc. 2010, 132, 6912-6913
20. Zhu, Z. L.; Wang, X. P.; Peng, Y.; Lei, H.; Fettinger, J. C.; Power, P. P. Angew. Chem., Int. Ed. 2009, 48, 2031-2034
21. Peng, Y.; Guo, J. D.; Ellis, B. D.; Zhu, Z. L.; Fettinger, J. C.; Power, P. P. J. Am. Chem. Soc. 2009, 131, 16272-16282
22. Khan, S.; Michel, R.; Sen, S. S.; Roesky, H. W.; Stalke, D. Angew. Chem., Int. Ed. 2011, 50, 11786-11789
23. Masuda, J. D.; Schoeller, W. W.; Donnadieu, B.; Bertrand, G. J. Am. Chem. Soc. 2007, 129, 14180-14181
24. Masuda, J. D.; Schoeller, W. W.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2007, 46, 7052-7055
25. Xiong, Y.; Yao, S.; Brym, M.; Driess, M. Angew. Chem., Int. Ed. 2007, 46, 4511-4513
26. Caputo, C. A.; Zhu, Z. L.; Brown, Z. D.; Fettinger, J. C.; Power, P. P. Chem. Commun. 2011, 47, 7506-7508
27. Peng, Y.; Ellis, B. D.; Wang, X. P.; Fettinger, J. C.; Power, P. P. Science 2009, 325, 1668-1670
28. McCahill, J. S. J.; Welch, G. C.; Stephan, D. W. Angew. Chem., Int. Ed. 2007, 46, 4968-4971
29. Breton, G. W.; Kropp, P. J. e-Encyclopedia of Reagents for Organic Synthesis; Wiley: New York, 2010, "Hydrazoic Acid".
30. Romeder, G. e-Encyclopedia of Reagents for Organic Synthesis; Wiley: New York, 2010, "Hydrogen Cyanide".
31. a values are almost always larger in organic solvents, where the solvent is not as effective at supporting the charges that develop upon ionization. See: Ansilyn, E. V.; Daugherty, D. A. Modern Physical Organic Chemistry; University Science Books: Sausalito, 2006; p 271.
32. Friestand, G. K.; Branchaud, B. P. e-Encyclopedia of Reagents for Organic Synthesis; Wiley: New York, 2010, "Tetrafluoroboric Acid".
33. Subramanian, L. R.; Martinex, A. G.; Hanack, M. e-Encyclopedia of Reagents for Organic Synthesis; Wiley: New York, 2010, " Trifluormethanesulfonic Acid".
34. Simons, R. S.; Pu, L. H.; Olmstead, M. M.; Power, P. P. Organometallics 1997, 16, 1920
35. Brown, Z. D.; Vasko, P.; Fettinger, J. C.; Tuononen, H. M.; Power, P. P. J. Am. Chem. Soc. 2012, 134, 4045-4048
36. SMART (Version 5.054) and SAINT (Version 7.46a); Bruker AXS Inc.: Madison, WI, USA, 2002.
37. Blessing, R. H. An Empirical Correction for Absorption Anisotropy Acta Crystallogr. 1995, A51, 33-38
38. Sheldrick, G. M. SADABS, Siemens Area Detector Absorption Correction; Universität Göttingen: Göttingen, Germany, 2008.
39. Sheldrick, G. M. SHELXS97 and SHELXL97; Universität Göttingen: Göttingen, Germany, 1997.
40. Morán, M.; Gayoso, M. J. Organomet. Chem. 1983, 243, 423-426
41. Shäfer, H.; Saak, W.; Weidenbruch, M. J. Organomet. Chem. 2000, 604, 211-213
42. Hihara, G.; Hynes, R. C.; Lebuis, A.-M.; Rivière-Baudet, M.; Wharf, I.; Onyszchuk, M. J. Organomet. Chem. 2000, 598, 276-285
43. Filippou, A. C.; Portius, P.; Kociok-Köhn, G. Chem. Commun. 1998, 2327-2328
44. Zigler, K. J.; Haller, R.; West; Gordon, M. S. Organometallics 1989, 8, 1656-1660
45. Pasceri, R.; Bartrum, H. E.; Hayes, C. J.; Moody, C. J. Chem. Commun. 2012, 10.1039/c2cc37284c
46. Lesbre, M.; Mazerolles, P.; Satgé, J. Organic Compounds of Germanium; Wiley: London, 1971; p 20.
47. Bourk, S. C.; MacLachlan, M. J.; Lough, A. J.; Manners, I. Chem.-Eur. J. 2005, 11, 1989-2000
48. Tamm, M.; Kunsh, A.; Bannenberg, T.; Randoll, S.; Jones, P. G. Organometallics 2007, 26, 417-424
49. Tetrafluorboric acid has been shown to effectively oxidize a germyl-rhenium complex featuring a triphenylgermane ligand. See: Lee, K. E.; Arif, A. M.; Gladysz, J. A. Organometallics 1991, 10, 751-760
50. Takeda, N.; Kajiwara, T.; Suzuki, H.; Okazaki, R.; Tokitoh, N. Chem.-Eur. J. 2003, 9, 3530-3543
51. Jutzi, P.; Kohl, F.; Hofmann, P.; Krüger, C.; Tsay, Y.-H. Chem. Ber. 1980, 113, 757-769
52. Reed, C. A. Acc. Chem. Res. 1998, 31, 325-332
53. Rupar, P. A.; Staroverov, V. N.; Baines, K. M. Science 2008, 322, 1360-1363
54. Rupar, P. A.; Bandyopadhyay, R.; Cooper, B. F. T.; Stinchcombe, M. R.; Ragogna, P. J.; Macdonald, C. L. B.; Baines, K. M. Angew. Chem., Int. Ed. 2009, 48, 5155-5158
55. Rupar, P. A.; Staroverov, V. N.; Baines, K. M. Organometallics 2010, 29, 4871-4881
56. Stender, M.; Phillips, A. D.; Power, P. P. Inorg. Chem. 2001, 40, 5314-5315
57. Xiong, Y.; Yao, S.; Inoue, S.; Berkfeld, A.; Driess, M. Chem. Commun. 2012, 48, 12198-1220
58. Li, J.; Schenk, C.; Winter, F.; Scherer, H.; Trapp, N.; Higelin, A.; Keller, S.; Pöttgen, R.; Krossing, I.; Jones, C. Angew. Chem., Int. Ed. 2012, 51, 9557-9561
59. Cosledan, F.; Rivière, C. P.; Satgé, J.; Veith, M.; Huch, V. Organometallics 1998, 17, 2222-2227
60. Antoniotti, P.; Grandinetti, F.; Volpe, P. J. Phys. Chem. 1995, 99, 17724-17728