Improved protocols for the molybdenum-catalyzed hydrostannation of alkynes

Synlett

Volumn , Issue 7, 2006, Pages 1105-1109

  Wesquet, Alexander O ^a   Dörrenbächer, Sandra ^a   Kazmaier, Uli ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Alkynes; Hydrostannation; Microwave; Molybdenum; Stannanes

Indexed keywords

(2 TRIBUTYLSTANNYL) N ALLYL PHTHALIMIDE; (2 TRIBUTYLSTANNYLPROP 2 ENE 1 SULFANYL)BENZENE; 1 (2 TRIBUTYLSTANNYLPROP 2 ENE 1 SULFANYL) 2,3,4,5,6 PENTAFLUOROBENZENE; 1 (ALLYLOXYMETHYLVINYL)TRIBUTYLSTANNANE; 2 (2 TRIBUTYLSTANNYLPROP 2 ENE 1 SULFONYL)PYRIDINE; 4 (2 TRIBUTYLSTANNYLPROP 2 ENE 1 SULFANYL)PYRIDINE; 4 NITROPHENYL (2 TRIBUTYLSTANNYL)ALLYLETHER; ALKYNE DERIVATIVE; MOLYBDENUM; TRIBUTYLTIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICROWAVE IRRADIATION; SYNTHESIS;

EID: 33646677930     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-939683     Document Type: Article

References (29)

1. Hegedus, L. S. Organische Synthese mit Übergangsmetallen; VCH: Weinheim, 1995.
2. A comprehensive survey on palladium-catalyzed reactions can be found in: Malleron, J. L.; Fiaud, J. C.; Legros, J. Y. Handbook of Palladium-Catalyzed Organic Reactions; Academic Press: San Diego, 1997.
3. (a) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
4. (b) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508;
5. Angew. Chem. 1986, 98, 504.
6. (c) Pereyre, M.; Quintard, J. P.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987.
7. (d) Davies, A. G. Organotin Chemistry; VCH: Weinheim, 1997.
8. (a) Davies, A. G. Comprehensive Organometallic Chemistry II, Vol. 2; Pergamon: Oxford, 1995, 217.
9. (b) Smith, N. D.; Mancuso, J.; Lautens, M. Chem. Rev. 2000, 100, 3257.
10. Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881.
11. Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857.
12. Leung, L. T.; Leung, S. K.; Chiu, P. Org. Lett. 2005, 7, 5249.
13. (a) Kazmaier, U.; Schauß, D.; Pohlman, M. Org. Lett. 1999, I, 1017.
14. (b) Kazmaier, U.; Pohlman, M.; Schauß, D. Eur. J. Org. Chem. 2000, 2761.
15. (c) Kazmaier, U.; Braune, S. J. Organomet. Chem. 2002, 641, 2629.
16. (d) Braune, S.; Pohlman, M.; Kazmaier, U. J. Org. Chem. 2004, 69, 468.
17. (e) Kazmaier, U.; Klein, M. Chem. Commun. 2005, 501.
18. (a) Kazmaier, U.; Schauß, D.; Pohlman, M.; Raddatz, S. Synthesis 2000, 914.
19. (b) Kazmaier, U.; Schauß, D.; Raddatz, S.; Pohlman, M. Chem. Eur. J. 2001, 7, 456.
20. 2Sn: C, 58.01 ; H, 7.41; N, 2.94.
21. Kazmaier, U.; Wesquet, A. O. Synlett 2005, 1271.
22. (a) Kocienski, P. J.; Lythgoe, B.; Ruston, S. J. Chem. Soc., Perkin Trans. 1 1978, 829.
23. (b) Kocienski, P. J.; Lythgoe, B.; Waterhouse, U. J. Chem. Soc., Perkin Trans. 1 1980, 1045.
24. A CEM Discover microwave oven was used.
25. For some representative examples of microwave-assisted cross-couplings and one-pot hydrostannation/Stille coupling reactions: (a) Larhed, M.; Hallberg, A. J. Org. Chem. 1996, 61, 9582.
26. (b) Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539.
27. Maleczka, R. E. Jr.; Lavis, J. M.; Clark, D. H.; Gallagher, W. P. Org. Lett. 2000, 2, 3655.
28. 3SnH (1.1 equiv) was added. After the flask was sealed under a dry argon atmosphere, the solution was heated in a microwave oven for 5-10 min at 100-250 W. After cooling, the reaction mixture was concentrated and the residue purified by chromatography (hexanes-EtOAc) to obtain the desired product as a colorless oil. Caution! The rapid increase in temperature and pressure may result in an explosion, therefore the microwave-assisted reactions should only be repeated in vessels with a suitable septum as a pressure-relief device.
29. m).