Palladium-catalyzed thiocarbonylation of aryl, vinyl, and benzyl bromides

Journal of Organic Chemistry

Volumn 79, Issue 24, 2014, Pages 11830-11840

  Burhardt, Mia N ^a   Ahlburg, Andreas ^a   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON MONOXIDE; CARBONYLATION; CHLORINE COMPOUNDS; METAL HALIDES; PALLADIUM; PALLADIUM COMPOUNDS; THIOPHENE;

CATALYTIC PROTOCOL; CATALYTIC SYSTEM; CHEMICAL EQUATIONS; CHEMO-SELECTIVITY; ELECTRON-DEFICIENT; PALLADIUM CHLORIDE; PALLADIUM-CATALYZED; TWO-CHAMBER SYSTEMS;

SYNTHESIS (CHEMICAL);

ALCOHOL; ANILINE; ANISOLE; ARYL; BENZOTHIOPHENE; BENZYL BROMIDE; BENZYL CHLORIDE; CARBON 13; DIGLYME; DIOXANE; INDOLE DERIVATIVE; NUCLEOPHILE; PALLADIUM; PALLADIUM COMPLEX; SODIUM IODIDE; THIOESTER; THIOPHENE; THIOPHENOL; TOLUENE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; BENZYL DERIVATIVE; CARBON; THIOL DERIVATIVE;

CARBONYLATION; CATALYST; COLUMN CHROMATOGRAPHY; CYCLIZATION; ELECTRON; NUCLEOPHILICITY; REACTION TIME; REVIEW; SUZUKI REACTION; SYNTHESIS; THIOCARBONYLATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

BENZYL COMPOUNDS; CARBON ISOTOPES; CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM; SULFHYDRYL COMPOUNDS; VINYL COMPOUNDS;

EID: 84919687882     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5009965     Document Type: Review

References (63)

1. Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 3189.
2. Mehta, V. P.; Sharma, A.; Van der Eycken, E. Org. Lett. 2008, 10, 1147.
3. Os'kina, I. A.; Vlasov, V. M. Russ. J. Org. Chem. 2009, 4, 523.
4. Ueda, M.; Seki, K.; Imai, Y. Synthesis 1981, 991.
5. Azuma, H.; Okano, K.; Tokuyama, H. Chem. Lett. 2011, 40, 959.
6. Fukuyama, T.; Lin, S. C.; Li, L. P. J. Am. Chem. Soc. 1990, 112, 7050.
7. Kotsuki, H.; Yoshimura, N.; Ushio, Y.; Ohtsuka, T.; Ochi, M. Chem. Lett. 1986, 1003.
8. Nagashima, E.; Suzuki, K.; Sekiya, M. Chem. Pharm. Bull. 1983, 31, 3306.
9. Yousif, N. M.; Pedersen, U.; Yde, B.; Lawesson, S. O. Tetrahedron 1984, 40, 2663.
10. Alvarez-Ibarra, C.; Mendoza, M.; Orellana, G.; Quiroga, M. L. Synthesis 1989, 560.
11. (a) Wu, X. F.; Neumann, H.; Beller, M. Chem. Rev. 2013, 113, 1.
12. (b) Odell, L. R.; Larhed, M. Synlett 2012, 685.
13. (c) Wu, W. F.; Neumann, H.; Beller, M. Chem. Soc. Rev. 2011, 40, 4986.
14. (d) Brennführer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114.
15. (e) Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177.
16. (f) Grigg, R.; Mutton, S. P. Tetrahedron 2010, 66, 5515.
17. (a) Baranano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937.
18. (b) Mann, G.; Baranano, D.; Hartwig, J. F.; Rheingold, A. L.; Guzei, I. A. J. Am. Chem. Soc. 1998, 120, 9205.
19. (c) Fernandez-Rodriguez, M. A.; Shen, Q. L.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180.
20. (d) Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534.
21. (e) Fernandez-Rodriguez, M. A.; Hartwig, J. F. J. Org. Chem. 2009, 74, 1663.
22. (f) Alvaro, E.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 7858.
23. (a) Xiao, W. J.; Alper, H. J. Org. Chem. 1997, 62, 3422.
24. (b) Xiao, W. J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1998, 63, 2609.
25. (c) Xiao, W. J.; Alper, H. J. Org. Chem. 1998, 63, 7939.
26. (d) Xiao, W. J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1999, 64, 2080.
27. (e) Xiao, W. J.; Alper, H. J. Org. Chem. 1999, 64, 9646.
28. (f) Xiao, W. J.; Vasapollo, G.; Alper, H. J. Org. Chem. 2000, 65, 4138.
29. (g) Xiao, W. J.; Alper, H. J. Org. Chem. 2001, 66, 6229.
30. (h) Xiao, W. J.; Alper, H. J. Org. Chem. 2005, 70, 1802.
31. (i) Cao, H.; Xiao, W. J.; Alper, H. Adv. Synth. Catal. 2006, 348, 1807.
32. (j) Li, C. F.; Xiao, W. J.; Alper, H. J. Org. Chem. 2009, 74, 888.
33. Cao, H.; McNamee, L.; Alper, H. J. Org. Chem. 2008, 73, 3530.
34. Hu, Y. H.; Liu, J.; Lu, Z. X.; Luo, X. C.; Zhang, H.; Lan, Y.; Lei, A. W. J. Am. Chem. Soc. 2010, 132, 3153.
35. Nakaya, R.; Yorimitsu, H.; Oshima, K. Chem. Lett. 2011, 40, 904.
36. Burhardt, M. N.; Taaning, R. H.; Skrydstrup, T. Org. Lett. 2013, 15, 948.
37. COgen is commercially available at: www.sigmaaldrich.com and www.sytracks.com.
38. Hermange, P.; Lindhardt, A. T.; Taaning, R. H.; Bjerglund, K.; Lupp, D.; Skrydstrup, T. J. Am. Chem. Soc. 2011, 133, 6061.
39. (a) Neumann, K. T.; Laursen, S. R.; Lindhardt, A. T.; Bang-Andersen, B.; Skrydstrup, T. Org. Lett. 2014, 16, 2216.
40. (b) Nielsen, D. U.; Lescot, C.; Gøgsig, T. M.; Lindhardt, A. T.; Skrydstrup, T. Chem. - Eur. J. 2013, 19, 17926.
41. (c) Korsager, S.; Nielsen, D. U.; Taaning, R. H.; Lindhardt, A. T.; Skrydstrup, T. Chem. - Eur. J. 2013, 19, 17687.
42. (d) Ahlburg, A.; Lindhardt, A. T.; Taaning, R. H.; Modvig, A. E.; Skrydstrup, T. J. Org. Chem. 2013, 78, 10310.
43. (e) Korsager, S.; Nielsen, D. U.; Taaning, R. H.; Skrydstrup, T. Angew. Chem., Int. Ed. 2013, 52, 9763.
44. (f) Gøgsig, T. M.; Taaning, R. H.; Lindhardt, A. T.; Skrydstrup, T. Angew. Chem., Int. Ed. 2012, 51, 798.
45. (g) Burhardt, M. N.; Taaning, R.; Nielsen, N. C.; Skrydstrup, T. J. Org. Chem. 2012, 77, 5357.
46. (h) Gøgsig, T. M.; Nielsen, D. U.; Lindhardt, A. T.; Skrydstrup, T. Org. Lett. 2012, 14, 2536
47. Lindhardt, A. T.; Simonssen, R.; Taaning, R. H.; Gøgsig, T. M.; Nilsson, G. N.; Stenhagen, G.; Elmore, C. S.; Skrydstrup, T. J. Labelled Compd. Radiopharm. 2012, 55, 411.
48. Martinelli, J. R.; Watson, D. A.; Freckmann, D. M. M; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2008, 73, 7102
49. Wu, X. F.; Neumann, H.; Spannenberg, A.; Schulz, T.; Jiao, H. J.; Beller, M. J. Am. Chem. Soc. 2010, 132, 14596
50. Ishiyama, T.; Kizaki, H.; Hayashi, T.; Suzuki, A.; Miyaura, N. J. Org. Chem. 1998, 63, 4726.
51. Ankersmit, H. A.; Witte, P. T.; Kooilman, H.; Lakin, M. T.; Spek, A. L.; Goubitz, K.; Vrieze, K.; vanKoten, G. Inorg. Chem. 1996, 35, 6053.
52. Quesnel, J. S.; Arndsen, B. A. J. Am. Chem. Soc. 2013, 135, 16841.
53. Zhan, F.; Liang, G. Angew. Chem., Int. Ed. 2013, 52, 1266.
54. Geng, W. Z.; Wang, H. L.; Wang, Z. T.; Zhang, S. G.; Zhang, W. X.; Xi, Z. F. Tetrahedron 2012, 68, 5283.
55. Katritzky, A. R.; Kirichenko, K.; Ji, Y.; Prakash, I. Chem. Heterocycl. Compd. 2002, 38, 156.
56. Perrin, D.; Armarego, W. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: New York, 1988.
57. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512.
58. Kuhakarn, C.; Surapanich, N.; Kamtonwong, S.; Pohmakotr, M.; Reutrakul, V. Eur. J. Org. Chem. 2011, 29, 5911.
59. Arisawa, M.; Igarashi, Y.; Kobayashi, H.; Yamada, T.; Bando, K.; Ichikawa, T.; Yamaguchi, M. Tetrahedron 2011, 67, 7846.
60. Cilento, G. J. Am. Chem. Soc. 1953, 75, 3748.
61. Xia, Z.; Lv, X.; Wang, W.; Wang, X. Tetrahedron Lett. 2011, 52, 4906.
62. Arnaudov, M. G.; Ivanova, B. B.; Prangova, L. S. J. Mol. Struct. 2003, 661, 219.
63. Hewkin, C. T.; Jackson, R. W.; William, C. J. Chem. Soc., Perkin Trans. 1 1991, 3091.