Palladium-catalyzed selective decarboxylative coupling reaction versus direct C - H arylation for arylation of heteroaromatics

Applied Organometallic Chemistry

Volumn 27, Issue 10, 2013, Pages 595-600

  Fu, Haiyan ^a,b   Chen, Hua ^a   Doucet, Henri ^b  

^a Sichuan University   (China)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

arylation; catalysis; decarboxylative coupling; furans; palladium; thiophenes

Indexed keywords

ARYLATIONS; DECARBOXYLATIVE COUPLINGS; DIMETHYLACETAMIDE; FURAN DERIVATIVES; FURANS; HETEROAROMATICS; PALLADIUM-CATALYZED; PHOSPHINE-FREE;

FUNCTIONAL GROUPS; ORGANIC POLLUTANTS; PALLADIUM; PHOSPHORUS COMPOUNDS; THIOPHENE;

CATALYSIS;

EID: 84884975378     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.3037     Document Type: Article

References (41)

1. a) J. K. Stille, Angew. Chem. Int. Ed. Engl. 1986, 25, 508
2. b) J. J. Li, G. W. Gribble, Palladium in Heterocyclic Chemistry, Pergamon, Amsterdam, 2000
3. c) N. Miyaura, Top. Curr. Chem. 2002, 219, 11.
4. A. Ohta, Y. Akita, T. Ohkuwa, M. Chiba, R. Fukunaga, A. Miyafuji, T. Nakata, N. Tani, Y. Aoyagi, Heterocycles 1990, 31, 1951.
5. a) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174
6. b) L.-C. Campeau, D. R. Stuart, K. Fagnou, Aldrichim. Acta 2007, 40, 35
7. c) I. V. Seregin, V. Gevoryan, Chem. Soc. Rev. 2007, 36, 1173
8. d) T. Satoh, M. Miura, Chem. Lett. 2007, 36, 200
9. e) C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013
10. f) O. Daugulis, H.-Q. Do, D. Skabashov, Acc. Chem. Res. 2009, 42, 1074
11. g) F. Bellina, R. Rossi, Tetrahedron 2009, 65, 10269
12. h) P. Thansandote, M. Lautens, Chem. Eur. J. 2009, 15, 5874
13. i) X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. Int. Ed. 2009, 48, 5094
14. j) L. Ackermann, R. Vicente, A. Kapdi, Angew. Chem. Int. Ed. 2009, 48, 9792
15. k) J. Roger, A. L. Gottumukkala, H. Doucet, ChemCatChem 2010, 2, 20
16. l) N. Kuhl, M. N. Hopkinson, J. Wencel-Delord, F. Glorius, Angew. Chem. Int. Ed. 2012, 51, 10236.
17. B. Glover, K. A. Harvey, B. Liu, M. J. Sharp, M. F. Tymoschenko, Org. Lett. 2003, 5, 301.
18. A. Borghese, G. Geldhof, L. Antoine, Tetrahedron Lett. 2006, 47, 9249.
19. P. Forgione, M.-C. Brochu, M. St-Onge, K. H. Thesen, M. D. Bailey, F. Bilodeau, J. Am. Chem. Soc. 2006, 128, 11350.
20. J. J. Dong, H. Doucet, Eur. J. Org. Chem. 2010, 611.
21. J. J. Dong, D. Roy, R. Jacob Roy, M. Ionita, H. Doucet, Synthesis 2011, 3530.
22. S. Tanaka, S. Tamba, D. Tanaka, A. Sugie, A. Mori, J. Am. Chem. Soc. 2011, 133, 16734.
23. L. Lavenot, C. Gozzi, K. Ilg, I. Orlova, V. Penalva, M. Lemaire, J. Organomet. Chem. 1998, 567, 49.
24. A. G. Myers, D. Tanaka, M. R. Mannion, J. Am. Chem. Soc. 2002, 124, 11250.
25. a) L. J. Goossen, G. Deng, L. M. Levy, Science 2006, 313, 662
26. b) L. J. Goossen, F. Rudolphi, C. Oppel, N. Rodriguez, Angew. Chem. Int. Ed. 2008, 47, 3043.
27. For recent reviews on decarboxylative cross-coupling reactions, see: a), L. J. Goossen, N. Rodriguez, K. Goossen, Angew. Chem. Int. Ed. 2008, 47, 3100
28. b) S. M. Bonesi, M. Fagnoni, Chem. Eur. J. 2010, 16, 13572
29. c) J. Cornella, I. Larrosa, Synthesis 2012, 44, 653.
30. For recent palladium-catalysed decarboxylative couplings reactions, see: a), P. Forgione, M.-C. Brochu, M. St-Onge, K. H. Thesen, M. D. Bailey, F. Bilodeau, J. Am. Chem. Soc. 2006, 128, 11350
31. b) L. J. Goossen, B. Zimmermann, C. Linder, N. Rodriguez, P. P. Lange, J. Hartung, Adv. Synth. Catal. 2009, 351, 2667
32. c) L. J. Goossen, C. Linder, N. Rodriguez, P. P. Lange, Chem. Eur. J. 2009, 15, 9336
33. d) F. Bilodeau, M.-C. Brochu, N. Guimond, K. H. Thesen, P. Forgione, J. Org. Chem. 2010, 75, 1550
34. e) Y. Jiang, Y. Fu, L. Liu, Sci. China Chem. 2012, 55, 2057
35. f) D. Nandi, Y.-M. Jhou, J.-Y. Lee, B.-C. Kuo, C.-Y. Liu, P.-W. Huang, H. M. Lee, J. Org. Chem. 2012, 77, 9384
36. g) P. Hu, M. Zhang, X. Jie, W. Su, Angew. Chem. Int. Ed. 2012, 51, 227
37. h) X. Li, D. Zou, F. Leng, C. Sun, J. Li, Y. Wu, Y. Wu, Chem. Commun. 2013, 49, 312.
38. H. Y. Fu, H. Doucet, Eur. J. Org. Chem. 2011, 7163.
39. T. Cantat, E. Génin, C. Giroud, G. Meyer, A. Jutand, J. Organomet. Chem. 2003, 687, 365.
40. a) A. I. Meyers, R. F. Spohn, J. Org. Chem. 1985, 50, 4872
41. b) J. Yu, N. Castagnoli Jr, Bioorg. Med. Chem. 1999, 7, 231