Carbon-sulfur bond formation catalyzed by [Pd(IPr*OMe) (cin)Cl] (cin = cinnamyl)

Journal of Organic Chemistry

Volumn 78, Issue 18, 2013, Pages 9303-9308

  Bastug, Gulluzar ^a   Nolan, Steven P ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLTHIOLS; ARYL HALIDES; CARBON SULFUR BONDS; CROSS COUPLING REACTIONS; N-HETEROCYCLIC CARBENES;

CARBON; ORGANIC COMPOUNDS; SULFUR;

PALLADIUM COMPOUNDS;

CARBENE; CARBON; HETEROCYCLIC COMPOUND; PALLADIUM; SULFUR;

ANION EXCHANGE; ARTICLE; CARBON SULFUR BOND; CATALYSIS; CHEMICAL BOND; CROSS COUPLING REACTION; NUCLEOPHILICITY; REACTION TIME; SUBSTITUTION REACTION;

EID: 84884554925     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401492n     Document Type: Article

References (53)

1. Thomas, G. L.; Spandl, R. J.; Glansdorp, F. G.; Welch, M.; Bender, A.; Cockfield, J.; Lindsay, J. A.; Bryant, C.; Brown, D. F. J.; Loiseleur, O.; Rudyk, H.; Ladlow, M.; Spring, D. R. Angew. Chem., Int. Ed. 2008, 47, 2808
2. Grand, B. L.; Pignier, C.; Letienne, R.; Cuisiat, F.; Rolland, F.; Mas, A.; Vacher, B. J. Med. Chem. 2008, 51, 3856
3. Inoue, H.; Konda, M.; Hashiyama, T.; Otsuka, H.; Takahashi, K.; Gaino, M.; Date, T.; Aoe, K.; Takeda, M.; Murata, S.; Narita, H.; Nagao, T. J. Med. Chem. 1991, 34, 675
4. Liu, G.; Link, J. T.; Pei, Z.; Reilly, E. B.; Leitza, S.; Nguyen, B.; Marsh, K. C.; Okasinski, G. F.; Von Geldern, T. W.; Ormes, M.; Fowler, K.; Gallatin, M. J. Med. Chem. 2000, 43, 4025
5. Nielsen, S. F.; Nielsen, E. O.; Olsen, G. M.; Liljefors, T.; Peters, D. J. Med. Chem. 2000, 43, 2217
6. Rayner, C. M. Advances in Sulfur Chemistry, Vol. 2; JAI Press: Greenwich, CT, 2000.
7. Voss, J.; Solladie, G.; Trost, B. M.; Fleming, I. In Comprehensive Organic Synthesis, Vol. 6; Pergamon Press: Oxford, U.K., 1991.
8. Wardell, J. L.; Patai, S. In The Chemistry of the Thiol Group; Wiley: Chichester, U.K., 1974.
9. Thuillier, A.; Metzner, P. Sulfur Reagents in Organic Synthesis; Academic Press: New York, 1994.
10. Paradisi, C.; Trost, B. M.; Fleming, I. In Comprehensive Organic Synthesis, Vol. 4; Pergamon Press: Oxford. U.K., 1991.
11. Caruso, A. J.; Colley, A. M.; Bryant, G. L. J. Org. Chem. 1991, 56, 862
12. Ham, J.; Yang, I.; Kang, H. J. Org. Chem. 2004, 69, 3236
13. Sandrinelli, F.; Perrio, S.; Averbuch-Pouchot, M.-T. Org. Lett. 2002, 4, 3619
14. Ullmann, F.; Sponagel, P. Ber. Dtsch. Chem. Ges. 1905, 38, 2211
15. Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312
16. Liebeskind, L. S.; Yang, H.; Li, H. Angew. Chem., Int. Ed. 2009, 48, 1417
17. Yu, Y.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2004, 6, 2631
18. Yu, Y.; Liebeskind, L. S. J. Org. Chem. 2004, 69, 3554
19. Wang, L.; He, W.; Yu, Z. Chem. Soc. Rev. 2013, 42, 599
20. Correa, A.; Mancheño, O. G.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108
21. Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596
22. Bichler, P.; Love, J. A. Top. Organomet. Chem. 2010, 31, 39-64
23. Eichman, C. C.; Stambuli, J. P. Molecules 2011, 16, 590
24. Cheng, J. H.; Ramesh, C.; Kao, H. L.; Wang, Y. J.; Chan, C. C.; Lee, C. F. J. Org. Chem. 2012, 77, 10369
25. Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-i.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385
26. Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 13
27. Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513
28. Li, G. Y. J. Org. Chem. 2002, 67, 3643
29. Murata, M.; Buchwald, S. L. Tetrahedron 2004, 60, 7397
30. Gao, G.-Y.; Colvin, A. J.; Chen, Y.; Zhang, X. P. J. Org. Chem. 2004, 69, 8886
31. Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587
32. Cai, L.; Cuevas, J.; Peng, Y.-Y.; Pike, V. W. Tetrahedron Lett. 2006, 47, 4449
33. Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1995, 36, 4133
34. Schopfer, U.; Schlapbach, A. Tetrahedron 2001, 57, 3069
35. Baranano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937
36. Fernández-Rodríguez, M. A.; Hartwig, J. F. J. Org. Chem. 2009, 74, 1663
37. Fernández-Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. Chem.-Eur. J. 2006, 12, 7782
38. Eichman, C. C.; Stambuli, J. P. J. Org. Chem. 2009, 74, 4005
39. Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205
40. Valente, C.; Çalimsiz, S.; Hoi, K. H.; Mallik, D.; Sayah, M.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 3314 and references cited therein
41. Wang, L.; Zhou, W.-Y.; Chen, S.-C.; He, M.-Y.; Chen, Q. Adv. Synth. Catal. 2012, 354, 839
42. Fu, C.-F.; Liu, Y.-H.; Peng, S.-M.; Liu, S.-T. Tetrahedron 2010, 66, 2119
43. Shi, Y.; Cai, Z.; Guan, P.; Pang, G. Synlett 2011, 2090
44. Sayah, M.; Organ, M. G. Chem.-Eur. J. 2011, 17, 11719
45. Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 6940
46. Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122
47. Fortman, G. C.; Nolan, S. P. Chem. Soc. Rev. 2011, 40, 5151
48. Díez-González, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612
49. Meiries, S.; Speck, K.; Cordes, D. B.; Slawin, A. M. Z.; Nolan, S. P. Organometallics 2013, 32, 330
50. Song, Y.-J.; Jung, I. G.; Lee, H.; Lee, Y. T.; Chung, Y. K.; Jang, H.-Y. Tetrahedron Lett. 2007, 48, 6142
51. Chartoire, A.; Lesieur, M.; Falivene, L.; Slawin, A. M. Z.; Cavallo, L.; Cazin, C. S. J.; Nolan, S. P. Chem.-Eur. J. 2012, 18, 4517
52. Sayah, M.; Lough, A. J.; Organ, M. G. Chem.-Eur. J. 2013, 19, 2749
53. Soria-Castro, S. M.; Peñéñory, A. B. Beilstein J. Org. Chem. 2013, 9, 467