A Palladium-catalyzed three-component-coupling strategy for the differential vicinal diarylation of terminal 1,3-dienes

Organic Letters

Volumn 16, Issue 17, 2014, Pages 4666-4669

  Stokes, Benjamin J ^a   Liao, Longyan ^a   De Andrade, Aline Mendes ^a   Wang, Qiaofeng ^a   Sigman, Matthew S ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE; BORONIC ACID DERIVATIVE; LIGAND; PALLADIUM;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKADIENES; ALKENES; BORONIC ACIDS; CATALYSIS; LIGANDS; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 84908382329     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502279u     Document Type: Article

References (30)

1. Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2001, 123, 8217
2. Svennebring, A.; Nilsson, P.; Larhed, M. J. Org. Chem. 2004, 69, 3345
3. Botella, L.; Nájera, C. J. Org. Chem. 2005, 70, 4360
4. Zou, G.; Huang, W.; Xiao, Y.; Tang, J. New J. Chem. 2006, 30, 803
5. Urkalan, K. B.; Sigman, M. S. Angew. Chem., Int. Ed. 2009, 48, 3146
6. Trejos, A.; Fardost, A.; Yahiaoui, S.; Larhed, M. Chem. Commun. 2009, 7587
7. Werner, E. W.; Urkalan, K. B.; Sigman, M. S. Org. Lett. 2010, 12, 2848
8. Xu, D.; Lu, C.; Chen, W. Tetrahedron 2012, 68, 1466
9. Oda, H.; Ito, K.; Kosugi, M.; Migita, T. Chem. Lett. 1994, 23, 1443
10. Huang, T.-H.; Chang, H.-M.; Wu, M.-Y.; Cheng, C.-H. J. Org. Chem. 2001, 67, 99
11. Saini, V.; Liao, L.; Wang, Q.; Jana, R.; Sigman, M. S. Org. Lett. 2013, 15, 5008
12. Liao, L.; Jana, R.; Urkalan, K. B.; Sigman, M. S. J. Am. Chem. Soc. 2011, 133, 5784
13. Saini, V.; Sigman, M. S. J. Am. Chem. Soc. 2012, 134, 11372
14. McCammant, M. S.; Liao, L.; Sigman, M. S. J. Am. Chem. Soc. 2013, 135, 4167
15. Reference 4.
16. For a review on the strategic control of β-hydride elimination in Pd-catalyzed alkene functionalization reactions, see: DeLuca, R. J.; Stokes, B. J.; Sigman, M. S. Pure Appl. Chem. 2014, 86, 395
17. Jutand, A.; Mosleh, A. Organometallics 1995, 14, 1810
18. Alcazar-Roman, L. M.; Hartwig, J. F. Organometallics 2002, 21, 491
19. Jutand, A.; Negri, S. Organometallics 2003, 22, 4229
20. Taylor, J. G.; Moro, A. V.; Correia, C. R. D. Eur. J. Org. Chem. 2011, 2011, 1403
21. Callonnec, F. o. L.; Fouquet, E.; Felpin, F. o.-X. Org. Lett. 2011, 13, 2646
22. Werner, E. W.; Sigman, M. S. J. Am. Chem. Soc. 2011, 133, 9692
23. Werner, E. W.; Mei, T.-S.; Burckle, A. J.; Sigman, M. S. Science 2012, 338, 1455
24. Oliveira, C. C.; Angnes, R. A.; Correia, C. R. D. J. Org. Chem. 2013, 78, 4373
25. Oger, N.; Le Callonnec, F.; Jacquemin, D.; Fouquet, E.; Le Grognec, E.; Felpin, F.-X. Adv. Synth. Catal. 2014, 356, 1065
26. The addition of exogenous dba has been effective in improving yields in alkene difunctionalization reactions. See: Saini, V.; Sigman, M. S. J. Am. Chem. Soc. 2012, 134, 11372
27. For a study of the steric inhibition of σ-π-σ isomerization of similar Pd-allyl intermediates, see: Liao, L.; Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 10209
28. For example, see: Thalén, L. K.; Sumic, A.; Bogár, K.; Norinder, J.; Persson, A. K. Å.; Bäckvall, J.-E. J. Org. Chem. 2010, 75, 6842
29. Stereospecific palladium-catalyzed arylations of enantiomerically enriched secondary styrenyl carbonates are challenging when a homostyrenyl arene is present because the carbonate is easily eliminated to give 1,4-diaryl-1,3-dienes. See: Zhao, J.; Ye, J.; Zhang, Y. J. Adv. Synth. Catal. 2013, 355, 491
30. For a review on the use of chiral olefins as ligands in asymmetric transition metal catalysis, see: Defieber, C.; Grützmacher, H.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 4482