Synthesis of aryl stannanes from silyl triflates via aryne intermediates

Synlett

Volumn , Issue 3, 2011, Pages 345-348

  Lakshmi, B Vasantha ^a   Wefelscheid, Ulrike K ^a   Kazmaier, Uli ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

aryl stannanes; arynes; hydrostannation; one pot reaction; Stille coupling

Indexed keywords

FLUORIDE; PHENYLSTANNANE; STANNANE DERIVATIVE; SULFONIC ACID DERIVATIVE; TETRABUTYLAMMONIUM; TETRABUTYLAMMONIUM FLUORIDE; TIN; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; HYBRID; HYDROSTANNATION; MICROWAVE IRRADIATION; NUCLEOPHILICITY; ONE POT SYNTHESIS; ROOM TEMPERATURE; SILYLATION; STILLE REACTION;

EID: 79551689147     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259311     Document Type: Article

References (38)

1. Stille J K., Angew. Chem., Int. Ed. Engl. 1986 25 508; Angew. Chem. 1986, 98, 504
2. Davies A G., In Comprehensive Organometallic Chemistry II Vol. 2 Pergamon New York 1995 217
3. Davies A G., Organotin Chemistry VCH Weinheim 1997
4. For reviews, see:, Smith N D., Mancuso J, Lautens M, Chem. Rev. 2000 100 3257
5. Trost B M., Ball Z T., Synthesis 2005 853; and references cited therein
6. Hayashi T, Ishigedani M, Tetrahedron 2001 57 2589
7. Gilman H, Rosenberg S D., J. Am. Chem. Soc. 1953 75 2507
8. Earbon C, Seconi G, J. Chem. Soc., Perkin Trans. 2 1976 925
9. Iddon B, Lim B L., J. Chem. Soc., Perkin Trans. 1 1983 271
10. Knochel P, Singer R D., Chem. Rev. 1993 93 2117
11. Zhu X, Blough B E., Caroll F I., Tetrahedron Lett. 2000 41 9219
12. Gosmini C, Perichon J, Org. Biomol. Chem. 2005 216
13. Kosugi M, Shiminu K, Ohtani A, Migita T, Chem. Lett. 1981 829
14. Kosugi M, Ohya T, Migita T, Bull. Chem. Soc. Jpn. 1983 56 3855
15. Lockhart M T., Chopa A B., Rossi R A., J. Organomet. Chem. 1999 582 229
16. Chopa A B., Lockhart M T., Silbestri G, Organometallics 2001 20 3358
17. Chopa A B., Lockhart M T., Silbestri G, Organometallics 2000 19 2249
18. Yoshida H, Tanino K, Ohshita J, Kunai A, Angew. Chem. Int. Ed. 2004 43 5052; Angew. Chem. 2004, 116, 5162
19. Yoshida H, Tanino K, Ohshita J, Kunai A, Chem. Commun. 2005 5678
20. Kazmaier U, Schauß D, Pohlman M, Org. Lett. 1999 1 1017
21. Kazmaier U, Pohlman M, Schauß D, Eur. J. Org. Chem. 2000 2761
22. Kazmaier U, Schauß D, Pohlman M, Raddatz S, Synthesis 2000 914
23. Kazmaier U, Schauß D, Raddatz S, Pohlman M, Chem. Eur. J. 2001 7 456
24. Braune S, Kazmaier U, J. Organomet. Chem. 2002 641 26
25. Braune S, Pohlman M, Kazmaier U, J. Org. Chem. 2004 69 468
26. Kazmaier U, Drrenbächer S, Wesquet A, Lucas S, Kummeter M, Synthesis 2007 320
27. Lakshmi B V., Kazmaier U, Synlett 2010 407
28. Himeshima Y, Sonoda T, Kobayashi H, Chem. Lett. 1983 1211
29. Peña D, Escudero S, Pérez D, Guitián E, Castedo L, Angew. Chem. Int. Ed. 1998 37 2659; Angew. Chem. 1998, 110, 2804. For this and other methods to generate arines and for applications see the following reviews
30. Pellissier H, Santelli M, Tetrahedron 2003 59 701
31. Yoshida H, Ohshita J, Kunai A, Bull. Chem. Soc. Jpn. 2010 83 199
32. Himeshima Y, Kobayashi H, Sonoda T, J. Am. Chem. Soc. 1985 107 5286
33. Peña D, Pérez D, Guitián E, Castedo L, J. Org. Chem. 2000 65 6944
34. Peña D, Cobas A, Pérez D, Guitián E, Synthesis 2002 1454
35. Zhijian L, Larock R C., J. Org. Chem. 2006 71 3198
36. Yoshida H, Terayama T, Ohshita J, Kunai A, Chem. Commun. 2004 1980
37. Lee K, Gallagher W P., Toskey E A., Chong W, Maleczka R E. Jr., J. Organomet. Chem. 2006 691 1462
38. Moriello, A. S.; Balas, L.; Ligresti, A.; Cascio, M. G.; Durand, T.; Morera, E.; Ortar, G.; Di Marzo, V. J. Med. Chem. 2006, 49, 2320.