Pd-catalyzed sequential C-C bond formation and cleavage: Evidence for an unexpected generation of arylpalladium(II) species

Journal of the American Chemical Society

Volumn 134, Issue 28, 2012, Pages 11308-11311

  Youn, So Won ^a   Kim, Byung Seok ^a   Jagdale, Arun R ^a  

^a Hanyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL; C-C BOND FORMATION; C-C BOND FORMING; CATALYZED REACTIONS; CLEAVAGE EVENTS; ELIMINATION PROCESS; IN-SITU; KETO ESTER; MECHANISTIC STUDIES; MIZOROKI-HECK REACTION; PD CATALYST;

PALLADIUM COMPOUNDS;

CATALYSIS;

1 NAPHTHOL; ALKENYL 1,3 DICARBONYL; ARYLPALLADIUM; CARBON; CARBONYL DERIVATIVE; PALLADIUM; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; MASS FRAGMENTOGRAPHY; MIZOROKI HECK REACTION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84863901402     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja304616q     Document Type: Article

References (40)

1. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
2. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
3. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
4. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
5. Murakami, M.; Matsuda, T. Chem. Commun. 2011, 47, 1100
6. Bonesi, S. M.; Fagnoni, M. Chem.-Eur. J. 2010, 16, 13572
7. Seiser, T.; Cramer, N. Org. Biomol. Chem. 2009, 7, 2835
8. Necas, D.; Kotora, M. Curr. Org. Chem. 2007, 11, 1566
9. Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610
10. Mitsudo, T.; Kondo, T. Synlett 2001, 309
11. Murakami, M.; Ito, Y. Top. Organomet. Chem. 1999, 3, 97
12. Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870
13. Aïssa, C. Synthesis 2011, 3389
14. Murakami, M.; Makino, M.; Ashida, S.; Matsuda, T. Bull. Chem. Soc. Jpn. 2006, 79, 1315
15. Satoh, T.; Miura, M. Top. Organomet. Chem. 2005, 14, 1
16. Terao, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2001, 123, 10407
17. Jagdale, A. R.; Youn, S. W. Eur. J. Org. Chem. 2011, 3904
18. Jagdale, A. R.; Park, J. H.; Youn, S. W. J. Org. Chem. 2011, 76, 7204
19. Zhou, C.-Y.; Che, C.-M. J. Am. Chem. Soc. 2007, 129, 5828
20. Pei, T.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11290
21. Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 2056
22. Cucciolito, M. E.; D'Amora, A.; Vitagliano, A. Organometallics 2010, 29, 5878
23. Li, Y.; Yu, Z.; Wu, S. J. Org. Chem. 2008, 73, 5647
24. Nguyen, R.-V.; Yao, X.-Q.; Bohle, D. S.; Li, C.-J. Org. Lett. 2005, 7, 673
25. Yao, X.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 6884
26. Han, X.; Widenhoefer, R. A. J. Org. Chem. 2004, 69, 1738
27. Pei, T.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 648
28. Trend, R. M.; Ramtohul, Y. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 17778
29. Trend, R. M.; Ramtohul, Y. K.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2003, 42, 2892
30. Pd-catalyzed intra- and intermolecular allylic alkylation between 1,3-dicarbonyls and alkenes: Lin, S.; Song, C.-X.; Cai, G.-X.; Wang, W.-H.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 12901
31. 3 for the synthesis of naphthols through 1,2-rearrangement of aryl groups: Shahzad, S. A.; Vivant, C.; Wirth, T. Org. Lett. 2010, 12, 1364
32. Heck, R. F. Acc. Chem. Res. 1979, 12, 146
33. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009
34. Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494
35. Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234
36. Chernyak, N.; Gorelsky, S. I.; Gevorgyan, V. Angew. Chem., Int. Ed. 2011, 50, 2342
37. Metz, A. E.; Berritt, S.; Dreher, S. D.; Kozlowski, M. C. Org. Lett. 2012, 14, 760
38. Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222
39. Halcrow, M. A.; Urbanos, F.; Chaudret, B. Organometallics 1993, 12, 955
40. Wang, A.; Jiang, H. J. Org. Chem. 2010, 75, 2321