Chemoselective tin-boron exchange aided by the use of dummy ligands at the tin atom

Organometallics

Volumn 33, Issue 19, 2014, Pages 5097-5100

  Hermeke, Julia ^a   Mewald, Marius ^a   Irran, Elisabeth ^a   Oestreich, Martin ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMOSELECTIVE; TIN ATOMS;

EID: 84908006895     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om500851r     Document Type: Article

References (38)

1. Brinckman, F. E.; Stone, F. G. A. Abstracts of Papers; 135th Meeting of the American Chemical Society, April 5-10, 1959, Boston, MA; American Chemical Society: Washington, DC, 1959; 26-M.
2. Brinckman, F. E.; Stone, F. G. A. Chem. Ind. 1959, 254-255
3. Niedenzu, K.; Dawson, J. W. J. Am. Chem. Soc. 1960, 82, 4223-4228
4. Burch, J. E.; Gerrard, W.; Howarth, M.; Mooney, E. F. J. Chem. Soc. 1960, 4916-4918
5. 3)-Sn (cf. Scheme 1, top). Conversely, steric factors are supposed to account for the preferred transmetalation of Me-Sn over Bn-Sn bonds (cf. Scheme 1, bottom). Electronic effects of substituents at the migrating group(s) might create exceptions from these general rules.
6. Paetzold, P. I.; Smolka, H. G. Chem. Ber. 1970, 103, 289-295
7. Gross, U.-M.; Bartels, M.; Kaufmann, D. J. Organomet. Chem. 1988, 344, 277-283
8. Mewald, M.; Fröhlich, R.; Oestreich, M. Chem. Eur. J. 2011, 17, 9406-9414
9. Erker, G. Dalton Trans. 2005, 1883-1890
10. Piers, W. E. Adv. Organomet. Chem. 2004, 52, 1-76
11. Piers, W. E.; Chivers, T. Chem. Soc. Rev. 1997, 26, 345-354
12. Chen, D.; Leich, V.; Pan, F.; Klankermayer, J. Chem. Eur. J. 2012, 18, 5184-5187
13. Mewald, M.; Oestreich, M. Chem. Eur. J. 2012, 18, 14079-14084
14. Hermeke, J.; Mewald, M.; Oestreich, M. J. Am. Chem. Soc. 2013, 135, 17537-17546
15. Chen, D.; Klankermayer, J. Chem. Commun. 2008, 2130-2131
16. Chen, D.; Wang, Y.; Klankermayer, J. Angew. Chem., Int. Ed. 2010, 49, 9475-9478
17. Sumerin, V.; Chernichenko, K.; Nieger, M.; Leskelä, M.; Rieger, B.; Repo, T. Adv. Synth. Catal. 2011, 353, 2093-2110
18. Ghattas, G.; Chen, D.; Fangfang, P.; Klankermayer, J. Dalton Trans. 2012, 41, 9026-9029
19. Liu, Y.; Du, H. J. Am. Chem. Soc. 2013, 135, 6810-6813
20. Topics in Current Chemistry; Erker, G.; Stephan, D. W., Eds.; Springer: Heidelberg, Germany, 2013; Vol. 332 (Frustrated Lewis Pairs I, Uncovering and Understanding).
21. Topics in Current Chemistry; Erker, G.; Stephan, D. W., Eds.; Springer: Heidelberg, Germany, 2013; Vol. 334 (Frustrated Lewis Pairs II, Expanding the Scope).
22. Sundararaman, A.; Jäkle, F. J. Organomet. Chem. 2003, 681, 134-142
23. 3, intermolecular)
24. 2BCl, intermolecular)
25. 3, inter-/intramolecular)
26. 2, intramolecular)
27. 2BCl, intermolecular)
28. 3, intermolecular)
29. 2BCl, intermolecular)
30. 3, intermolecular)
31. Bertz, S. H.; Eriksson, M.; Miao, G.; Snyder, J. P. J. Am. Chem. Soc. 1996, 118, 10906-10907
32. Berger, S.; Langer, F.; Lutz, C.; Knochel, P.; Mobley, T. A.; Reddy, C. K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1496-1498
33. Nanni, D.; Curran, D. P. Tetrahedron: Asymmetry 1996, 7, 2417-2422
34. Compound 13 was reported by Yanagisawa and co-workers in several publications, yet without characterization data. For its first appearance in the literature, see: Izumiseki, A.; Yoshida, K.; Yanagisawa, A. Org. Lett. 2009, 11, 5310-5313
35. Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139-5151
36. Chong, J. M.; MacDonald, G. K.; Park, S. B.; Wilkinson, S. H. J. Org. Chem. 1993, 58, 1266-1268
37. Laurence, C.; Gal, J.-F.; Lewis Basicity and Affinity Scales; Wiley: Chichester, U.K., 2010.
38. Chase, P. A.; Henderson, L. D.; Piers, W. E.; Parvez, M.; Clegg, W.; Elsegood, M. R. J. Organometallics 2006, 25, 349-357