Gold(I)-catalyzed synthesis of (1E,3E)-dienes from propargylic esters

Journal of Organometallic Chemistry

Volumn 694, Issue 4, 2009, Pages 482-485

  Dudnik, Alexander S ^a   Schwier, Todd ^a   Gevorgyan, Vladimir ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

1,3 Dienes; Gold; Homogeneous catalysis; Propargylic esters; Rearrangement

Indexed keywords

CATALYSIS; ESTERIFICATION; FOURIER TRANSFORMS; GOLD; GOLD COMPOUNDS; ORGANIC COMPOUNDS; PROTON TRANSFER; REACTION KINETICS;

1,3-DIENES; CASCADE PROCESSES; DOMINO TRANSFORMATION; HOMOGENEOUS CATALYSIS; PHOSPHATYLOXY MIGRATIONS; PROPARGYLIC ESTERS; REARRANGEMENT;

ESTERS;

EID: 58649104163     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.08.010     Document Type: Article

References (43)

1. For recent reviews, see:. Marco-Contelles J., and Soriano E. Chem. Eur. J. 13 (2007) 1350
2. Marion N., and Nolan S.P. Angew. Chem., Int. Ed. 46 (2007) 2750
3. For recent reviews, see:. Ma S., Yu S., and Gu Z. Angew. Chem., Int. Ed. 45 (2006) 200
4. Hashmi A.S.K. Angew. Chem., Int. Ed. 44 (2005) 6990
5. Hoffmann-Röder A., and Krause N. Org. Biomol. Chem. 3 (2005) 387
6. Echavarren A.M., and Nevado C. Chem. Soc. Rev. 33 (2004) 431
7. Dyker G. Angew. Chem., Int. Ed. 39 (2000) 4237
8. Hashmi A.S.K. Chem. Rev. 107 (2007) 3180
9. Hashmi A.S.K., and Hutchings G.J. Angew. Chem., Int. Ed. 45 (2006) 7896
10. Fürstner A., and Davies P.W. Angew. Chem., Int. Ed. 46 (2007) 3410
11. Yamamoto Y. J. Org. Chem. 72 (2007) 7817
12. Zhang L., Sun J., and Kozmin S.A. Adv. Synth. Catal. 348 (2006) 2271
13. Widenhoefer R.A., and Han X. Eur. J. Org. Chem. (2006) 4555
14. Ishida T., and Haruta M. Angew. Chem., Int. Ed. 46 (2007) 7154
15. Gorin D.J., and Toste F.D. Nature 446 (2007) 395
16. Amijs C.H.M., López-Carrillo V., and Echavarren A.M. Org. Lett. 9 (2007) 4021
17. Yu M., Zhang G., and Zhang L. Org. Lett. 9 (2007) 2147
18. Wang S., and Zhang L. J. Am. Chem. Soc. 128 (2006) 8414
19. Lemière G., Gandon V., Cariou K., Fukuyama T., Dhimane A.-L., Fensterbank L., and Malacria M. Org. Lett. 9 (2007) 2207
20. Buzas A., and Gagosz F. J. Am. Chem. Soc. 128 (2006) 12614
21. Marion N., Díez-González S., Frémont P., Noble A.R., and Nolan S.P. Angew. Chem., Int. Ed. 45 (2006) 3647
22. Zhang L., and Wang S. J. Am. Chem. Soc. 128 (2006) 1442
23. Buzas A., Istrate F., and Gagosz F. Org. Lett. 8 (2006) 1957
24. Zhang L. J. Am. Chem. Soc. 127 (2005) 16804
25. Sromek A.W., Kel'in A.V., and Gevorgyan V. Angew. Chem., Int. Ed. 43 (2004) 2280
26. Schwier T., Sromek A.W., Yap D.M.L., Chernyak D., and Gevorgyan V. J. Am. Chem. Soc. 129 (2007) 9868
27. For Au(I)-catalyzed synthesis of 2-acyloxy-1,3-dienes from allenes via formal 1,3-acyloxy migration, see:. Buzas A., Istrate F., and Gagosz F. Org. Lett. 9 (2007) 985
28. Wang S., and Zhang L. Org. Lett. 8 (2006) 4585
29. Li G., Zhang G., and Zhang L. J. Am. Chem. Soc. 130 (2008) 3740
30. Dudnik A.S., Schwier T., and Gevorgyan V. Org. Lett. 10 (2008) 1465
31. For general review, see:. Ducrot P.H. In: Katritzky A.R., and Taylor R.J.K. (Eds). Comprehensive Organic Functional Group Transformations II vol. 1 (2005), Elsevier, Oxford, UK 375-426
32. Saucy G., Marbet R., Lindlar H., and Isler O. Helv. Chim. Acta 42 (1959) 1945
33. Schlossarczyk H., Sieber W., Hesse M., Hansen H.-J., and Schmid H. Helv. Chim. Acta 56 (1973) 875
34. Cookson R.C., Cramp M.C., and Parsons P.J. J. Chem. Soc., Chem. Commun. (1980) 197
35. There has been a recent discussion on the role of Brønsted acids in homogenous transition metal-catalyzed reactions. For the most relevant references, see:. Hashmi A.S.K. Catal. Today 122 (2007) 211
36. Li Z., Zhang J., Brouwer C., Yang C.-G., Reich N.W., and He C. Org. Lett. 8 (2006) 4175
37. Rosenfeld D.C., Shekhar S., Takemiya A., Utsunomiya M., and Hartwig J.F. Org. Lett. 8 (2006) 4179
38. Rhee J.U., and Krische M.J. Org. Lett. 7 (2005) 2493
39. 4P: 282.10210. Found: 282.10225%.
40. Unfortunately, employment of internal alkynes possessing alkyl- and aryl substituents in this transformation led to unseparable mixtures of 1,3-dienes in low yields.
41. For reviews, see:. Allin S.M., and Baird R.D. Curr. Org. Chem. 5 (2001) 395
42. Nubbemeyer U. Synthesis 7 (2003) 961
43. Fanning K.N., Jamieson A.G., and Sutherland A. Curr. Org. Chem. 10 (2006) 1007