Flow heck reactions using extremely low loadings of phosphine-free palladium acetate

Organic Letters

Volumn 15, Issue 17, 2013, Pages 4342-4345

  Cyr, Patrick ^a   Deng, Stella T ^a   Hawkins, Joel M ^a   Price, Kristin E ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; BROMINATED HYDROCARBON; IODINATED HYDROCARBON; LIGAND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; TEMPERATURE;

ACETATES; CATALYSIS; HYDROCARBONS, BROMINATED; HYDROCARBONS, IODINATED; LIGANDS; MOLECULAR STRUCTURE; PALLADIUM; TEMPERATURE;

EID: 84883823116     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4018134     Document Type: Article

References (28)

1. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066
2. Heck, R. F. Acc. Chem. Res. 1979, 12, 146-151
3. Schmidt, A. F.; Al Halaiqa, A.; Smirnov, V. V. Synlett 2006, 18, 2861-2878
4. Diek, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133-1136
5. Herrmann, W. A.; Brossmer, C.; Ofele, K.; Reisinger, C. P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844-1848
6. Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000
7. Ripin, D. H. B.; Bourassa, D. E.; Brandt, T.; Castaldi, M. J.; Frost, H. N.; Hawkins, J.; Johnson, P. H.; Massett, S. S.; Neumann, K.; Phillips, J.; Raggon, J. W.; Rose, P. R.; Rutherford, J. L.; Sitter, B.; Stewart, A. M., III; Vetelino, M. G.; Wei, L. Org. Process Res. Dev. 2005, 9, 440-450
8. Jiang, X.; Lee, G. T.; Prasad, K.; Repic, O. Org. Process Res. Dev. 2008, 12, 1137-1141
9. Caron, S.; Vazquez, E.; Stevens, R. W.; Nakao, K.; Koike, H.; Murata, Y. J. Org. Chem. 2003, 68, 4104-4107
10. Chekal, B. P.; Guinness, S. M.; Lillie, B. M.; McLaughlin, R. W.; Palmer, C. W.; Post, R. J.; Sieser, J. E.; Singer, R. A.; Sluggett, G. W.; Vaidyanathan, R.; Withbroe, G. J. Org. Process Res. Dev. 2013, ASAP; DOI: 10.1021/op400088k.
11. Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177-2250
12. Konigsberger, K.; Chen, G. P.; Wu, R. R.; Girgis, M. J.; Prasad, K.; Repic, O.; Blacklock, T. J. Org. Process Res. Dev. 2003, 7, 733-742
13. Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37, 2320-2322
14. Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581
15. Jeffery, T. Adv. Met.-Org. Chem. 1996, 5, 153-260
16. Reetz, M. T.; de Vries, J. G. Chem. Commun. 2004, 1559-1563
17. Gurtler, C.; Buchwald, S. L. Chem.-Eur. J. 1999, 5, 3107-3112
18. Mason, B. P.; Price, K. E.; Steinbacher, J. L.; Bogdan, A. R.; McQuade, D. T. Chem. Rev. 2007, 107, 2300-2318
19. Noel, T.; Buchwald, S. L. Chem. Soc. Rev. 2011, 40, 5010-5029
20. Glasnov, T. N.; Findenig, S.; Kappe, C. O. Chem.-Eur. J. 2009, 15, 1001-1010
21. Conjure and Propel flow systems were used for these experiments (www.accendocorporation.com).
22. Bogdan, A. R.; Sach, N. W. Adv. Synth. Catal. 2009, 351, 849-854
23. (NMP/NaOAc) de Vries, A. H. M.; Mulders, J. M. C. A.; Mommers, J. H. M.; Henderickx, H. J. W.; deVries, J. G. Org. Lett. 2003, 5, 3285-3288
24. (NMP/DMG/NaOAc) Reetz, M. T.; Westermann, E.; Lohmer, R.; Lohmer, G. Tetrahedron Lett. 1998, 39, 8449-8452
25. 2NMe) Gurtler, C.; Buchwald, S. L. Chem.-Eur. J. 1999, 5, 3107-3112
26. For more information on resting states: Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000
27. Evans, J.; O'Neill, L.; Kambhampati, V. L.; Rayner, G.; Turin, S.; Genge, A.; Dent, A. J.; Neisius, T. J. Chem. Soc., Dalton Trans. 2002, 2207-2212
28. Figure 2 is a small multiple graph. For more information on small multiples, see: Tufte, E. R. The Visual Display of Quantitative Information, 2 nd ed.; Graphics Press LLC: Cheshire, CT, 2001; p 42.