Stille reactions with tetraalkylstannanes and phenyltrialkylstannanes in low melting sugar-urea-salt mixtures

Advanced Synthesis and Catalysis

Volumn 348, Issue 15, 2006, Pages 2243-2247

  Imperato, Giovanni ^a   Vasold, Rudolf ^a   König, Burkhard ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Carbohydrates; Green chemistry; Palladium; Stille coupling; Turnover number

Indexed keywords

EID: 33750500337     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600248     Document Type: Review

References (28)

1. V. Farina, V. Krishnamurthy, W. J. Scott, Org. React. 1997, 50, 1-652.
2. M. Kosugi, K. Fugami, in: Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.: E. Negishi), Wiley-Interscience, New York, 2002, pp. 263-283.
3. nd edn., Wiley-VCH, Weinheim, 2004.
4. P. Espinet, A. M. Echavarren, Angew. Chem. Int. Ed. 2004, 43, 4704-4734.
5. a) D. Milstein, J. K. Stille, J. Am. Chem. Soc. 1979, 101, 4992-4998;
6. b) methylation using diazonium salts: K. Kikukawa, K. Kono, F. Wada, T. Matsuda, J. Org. Chem. 1983, 48, 1333-1336;
7. c) vinyl triflates: W. J. Scott, G. T. Crisp, J. K. Stille, J. Am. Chem. Soc. 1984, 106, 4630-4632;
8. d) Vinyl iodides: W. F. Goure, M. E. Wright, P. D. Davis, S. S. Labadie, J. K. Stille, J. Am. Chem. Soc 1984, 106, 6417-6422.
9. a) The addition of copper(I) generally improves the yields of the Stille reaction: V. Farina, S. Kapadia, B. Krishnan, C. Wang, L. S. Liebeskind, J. Org. Chem. 1994, 59, 5905-5911;
10. b) use of nickel catalysts in carbonylative methylation: M. Tanaka, Synthesis 1981, 47.
11. M. T. Barros, C. D. Maycock, M. I. Madureira, M. R. Ventura, Chem. Commun. 2001, 1662-1663.
12. D. A. Powell, T. Maki, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 510-511.
13. For a recent examples, see: a) M. S. Jensen, C. Yang, Y. Hsiao, N. Rivera, K. M. Wells, J. Y. L. Chung, N. Yasuda, D. L. Hughes, P. J. Reider, Org. Lett. 2000, 2, 1081-1084;
14. b) A. I. Roshchin, N. A. Bumagin, I. P. Beletskaya, Tetrahedron Lett. 1995, 36, 125-128;
15. c) E. Fouquet, M. Pereyre, A. L. Rodriguez, J. Org. Chem. 1997, 62, 5242-5243;
16. d) "ligandless" conditions: A. Herve, A. L. Rodriguez, E. Fouquet, E. J. Org. Chem. 2005, 70, 1953-1956.
17. C. Chiappe, G. Imperato, E. Napolitano, D. Pieraccini, Green Chem. 2004, 6, 33-36.
18. C. Chiappe, D. Pieraccini, D. Zhao, Z. Fei, P. J. Dyson, Adv. Synth. Catal. 2006, 348, 68-74.
19. K. C. Nicolaou, C. N. C. Boddy, S. Brase, N. Winssinger, Angew. Chem. Int. Ed. 1999, 38, 2096;
20. S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633;
21. A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 4176.
22. Based on commercial prices for fine chemicals, which do not fully reflect bulk material cost, the cost of the sorbitol melt, entry 2 in Table 1, is estimated to be approx. € 18.00/kg. Prices for DMSO, as a solvent with comparable properties strongly depend on solvent purity and are in the order of € 60.00/kg.
23. th edn, Merck, 1989.
24. G. Imperato, E. Eibler, J. Niedermaier, B. König, Chem. Commun. 2005, 1170-1172. The thermal stability of the melts was determined by differential scanning calorimetry; data are given in the supporting information of the communication.
25. The estimated polarity of the melts from solvatochromic measurements is between DMSO and water: G. Imperato, S. Höger, D. Lenoir, B. König, Green Chem. 2006, DOI: 10.1039/6603660k.
26. E. Napolitano, V. Farina, M. Persico, Organometallics 2003, 22, 4030-4037. We underline that the concept of nucleophilic assistance is only advanced on the basis of simple kinetics and theoretical calculations and remains therefore speculative.
27. Melts containing dimethylurea are thermally more stable than urea melts, which may produce ammonia at elevated temperatures.
28. No flash points are available for the components of the melt. Only urea and dimethylurea have a significant vapor pressure and sublime in vacuum.