Enol tosylates as viable partners in Pd-catalyzed cross-coupling reactions

Journal of Organic Chemistry

Volumn 70, Issue 24, 2005, Pages 10124-10127

  Steinhuebel, Dietrich ^a   Baxter, Jenny M ^a,b   Palucki, Michael ^a   Davies, Ian W ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CROSSLINKING; ESTERS; PALLADIUM; REACTION KINETICS; SUBSTRATES; UNSATURATED COMPOUNDS;

CROSS-COUPLING REACTIONS; ENOL TOSYLATES; UNSATURATED ESTERS;

ALCOHOLS;

PALLADIUM; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; REACTION ANALYSIS; SONOGASHIRA REACTION; STEREOCHEMISTRY; STILLE REACTION; SUZUKI MIYAURA REACTION;

CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM; TOSYL COMPOUNDS;

EID: 28044437338     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051590s     Document Type: Article

References (36)

1. Huffman, M.; Yasuda, N. Synlett 1999, 4, 471-473.
2. Fu, X.; Zhang, S.; Yin, J.; McAllister, T. L.; Jiang, S. A.; Tann, C.; Thiruvengadam, T. K.; Zhang, F. Tetrahedron Lett. 2002, 43, 573-576
3. . Wu, J.; Liao, Y.; Yang, Z. J. Org. Chem. 2001, 66, 3642-3645.
4. Schio, L.; Chatreaux, F.; Klich, M. Tetrahedron Lett. 2000, 41, 1542
5. . Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 8704-8705.
6. Klapars, A.; Campos, K. R.; Chen, C. Y.; Volante, R. P. Org. Lett. 2005, 7, 1185-1188.
7. For phenyl besylate, see: Badone, D.; Cecchi, R.; Guzzi, U. J. Org. Chem. 1992, 57, 6321-6323.
8. Wu, J.; Zhu, Q.; Wang, L.; Fathi, R.; Yang, Z. J. Org. Chem. 2003, 68, 670-673.
9. Baxter, J. M.; Steinhuebel, D.; Palucki, M.; Davies, I. W. Org. Lett. 2005, 7, 215-218.
10. 3 at ambient temperature.
11. 3 in THF.
12. Mu, Y.; Gibbs, R. A. Tetrahedron Lett. 1995, 36, 5669-5672.
13. Molander, G. A.; Yun, C. Tetrahedron 2002, 58, 1465-1470.
14. Batey, R. A.; Thadani, A. N.; Smil, D. V. Org. Lett. 1999, 1, 1683-1686.
15. Molander, G. A.; Ito, T. Org. Lett. 2001, 3, 393-396.
16. Molander, G. A.; Rivero, M. R. Org. Lett. 2002, 4, 107-109.
17. 2 with 5b (see ref 3).
18. After 6 h, 87% conversion of 5b is observed and 27% of the undesired (E)-ester is present. Only the (E)-ester is detected after heating overnight.
19. 3N (1 equiv) in n-PrOH (0.06 M).
20. 3.
21. 3, and 1.2 equiv of styrenyltrifluoroborate.
22. 3 in THF were heated for 20 h at 60 °C. No conversion to product was observed.
23. Gebauer, O.; Bruckner, R. Synthesis 2000, 4, 588-602.
24. Casey, C. P.; Strotman, N. A. J. Org. Chem. 2005, 70, 2576-2581.
25. Nielsen, M. B.; Diederich, F. Chem. Rev. 2005, 105, 1837-1867.
26. Hayford, A.; Kaloko, J.; El-Kazaz, S.; Bass, G.; Harrison, C.; Corpew, T. Org. Lett. 2005, 7, 2671-2673.
27. 3CN with 2 equiv of DABCO.
28. Only 1 equiv, instead of 2 equiv, of DABCO is used in the coupling of the (E)-enol tosylate.
29. Soheili, A.; Albaneze-Walker, J.; Murry, J.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191-4194.
30. Complete conversion of enol tosylate is observed under the reaction conditions.
31. Twelve percent decomposition of enol tosylate 5b is observed at room temperature in THF in the presence of PhZnBr.
32. Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835-846.
33. Denmark, S. E.; Sweis, R. F. Org. Lett. 2002, 4, 3771-3774.
34. 2O.
35. 3 in toluene, 85 °C overnight.
36. Significant decomposition of enol tosylate 5b did not occur under reactions conditions.