Thioetherification of Chloroheteroarenes: A Binuclear Catalyst Promotes Wide Scope and High Functional-Group Tolerance

Chemistry - A European Journal

Volumn 20, Issue 39, 2014, Pages 12584-12594

  Platon, Mélanie ^a   Wijaya, Novi ^b   Rampazzi, Vincent ^a   Cui, Luchao ^b   Rousselin, Yoann ^a   Saeys, Mark ^b   Hierso, Jean Cyrille ^a,c  

^a UNIVERSITÉ DE BOURGOGNE   (France)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^c INSTITUT UNIVERSITAIRE DE FRANCE   (France)

Author keywords

binuclear catalyst; density functional calculations; phosphane ligands; tetradentate ligands; thioetherification

Indexed keywords

DENSITY FUNCTIONAL THEORY; LIGANDS; PALLADIUM; PYRIDINE;

CATALYST ACTIVATION; FUNCTIONALIZED PYRIDINES; PALLADIUM CATALYST; PALLADIUM LOADING; PHOSPHANE LIGANDS; REACTIVE FUNCTIONS; TETRADENTATE LIGANDS; THIOETHERIFICATION;

CATALYSTS;

EID: 84982263934     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201403337     Document Type: Article

References (56)

1. Z. Yu in Homogeneous Catalysis for Unreactive Bond Activation (Ed.: Z.-J. Shi), Wiley-VCH, Weinheim, 2014;
2. L. Wang, W. Hea, Z. Yu, Chem. Soc. Rev. 2013, 42, 599;
3. L. Ackermann, Modern Arylation Methods, Wiley-VCH, Weinheim, 2009.
4. P. Emond, J. Vercouillie, R. Innis, S. Chalon, S. Mavel, Y. Frangin, C. Halldin, J.-C. Besnard, D. Guilloteau, J. Med. Chem. 2002, 45, 1253;
5. B. C. H. May, J. A. Zorn, J. Witkop, A. C. Wallace, G. Legname, S. B. Prusiner, F. E. Cohen, J. Med. Chem. 2007, 50, 65.
6. M. Kosugi, T. Shimizu, T. Migita, Chem. Lett. 1978, 13–14;
7. T. Migita, T. Shimizu, Y. Asami, J. Shiobara, Y. Kato, M. Kosugi, Bull. Chem. Soc. Jpn. 1980, 53, 1385–1389;
8. M. Kosugi, M. Kameyama, T. Migita, Chem. Lett. 1983, 927.
9. G. Y. Li, Angew. Chem. 2001, 113, 1561;
10. Angew. Chem. Int. Ed. 2001, 40, 1513.
11. U. Schopfer, A. Schlapbach, Tetrahedron 2001, 57, 3069.
12. T. Itoh, T. Mase, Org. Lett. 2004, 6, 4587.
13. M. Murata, S. L. Buchwald, Tetrahedron 2004, 60, 7397.
14. C. Mispelaere-Canivet, J.-F. Spindler, S. Perrio, P. Beslin, Tetrahedron 2005, 61, 5253–5259.
15. M. A. Fernández-Rodríguez, Q. Shen, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 2180;
16. M. A. Fernández-Rodríguez, J. F. Hartwig, Chem. Eur. J. 2006, 12, 7782.
17. C. C. Eichman, J. P. Stambuli, J. Org. Chem. 2009, 74, 4005.
18. C.-F. Fu, Y.-H. Liu, S.-M. Peng, S.-T. Liu, Tetrahedron 2010, 66, 2119.
19. For representative examples, see:
20. L. Rout, T. K. Sen, T. Punniyamurthy, Angew. Chem. 2007, 119, 5679;
21. Angew. Chem. Int. Ed. 2007, 46, 5583;
22. M. Carril, R. SanMartin, E. Domínguez, I. Tellitu, Chem. Eur. J. 2007, 13, 5100;
23. R. Xu, J.-P. Wan, H. Mao, Y. Pan, J. Am. Chem. Soc. 2010, 132, 15531.
24. From iron salts, see:
25. A. Correa, M. Carril, C. Bolm, Angew. Chem. 2008, 120, 2922;
26. Angew. Chem. Int. Ed. 2008, 47, 2880;
27. J.-R. Wu, C.-H. Lin, C.-F. Lee, Chem. Commun. 2009, 4450; from cobalt, see:
28. Y.-C. Wong, T. T. Jayanth, C.-H. Cheng, Org. Lett. 2006, 8, 5613.
29. From bimetallic systems, see for Fe/Cu:
30. X. Ku, H. Hang, H. Jiang, H. Liu, J. Comb. Chem. 2009, 11, 338; see for Pd/Cu:
31. Z. Duan, S. Ranjit, P. Zhang, X. Liu, Chem. Eur. J. 2009, 15, 3666.
32. E. Alvaro, J. F. Hartwig, J. Am. Chem. Soc. 2009, 131, 7858;
33. G. Mann, D. Baranano, J. F. Hartwig, A. L. Rheingold, I. A. Guzei, J. Am. Chem. Soc. 1998, 120, 9205;
34. D. Baranano, J. F. Hartwig, J. Am. Chem. Soc. 1995, 117, 2937;
35. S. Shekhar, P. Ryberg, J. F. Hartwig, J. S. Mathew, D. G. Blackmond, E. R. Strieter, S. L. Buchwald, J. Am. Chem. Soc. 2006, 128, 3584.
36. J. F. Hartwig, Acc. Chem. Res. 2008, 41, 1534.
37. T. Yamamoto, Y. Sekine, Inorg. Chim. Acta 1984, 83, 47.
38. T. Kondo, T.-a. Mitsudo, Chem. Rev. 2000, 100, 3205;
39. I. P. Beletskaya, V. P. Ananikov, Chem. Rev. 2011, 111, 1596.
40. J.-C. Hierso, A. Fihri, V. V. Ivanov, B. Hanquet, N. Pirio, B. Donnadieu, B. Rebière, R. Amardeil, P. Meunier, J. Am. Chem. Soc. 2004, 126, 11077.
41. J.-C. Hierso, A. Fihri, R. Amardeil, P. Meunier, H. Doucet, M. Santelli, V. V. Ivanov, Org. Lett. 2004, 6, 3473.
42. D. Roy, S. Mom, M. Beaupérin, H. Doucet, J.-C. Hierso, Angew. Chem. 2010, 122, 6800;
43. Angew. Chem. Int. Ed. 2010, 49, 6650;
44. D. Roy, S. Mom, D. Lucas, H. Cattey, J.-C. Hierso, H. Doucet, Chem. Eur. J. 2011, 17, 6453.
45. M. Platon, L. Cui, S. Mom, P. Richard, M. Saeys, J.-C. Hierso, Adv. Synth. Catal. 2011, 353, 3403.
46. As reported in reference [10], in the presence of 2 mol % Pd, only a 47 % yield of 3 b was achieved while all other related thioethers were easily formed.
47. 3-Halopyridines are notably difficult to couple by transition-metal-catalyzed reactions; see:
48. O. Navarro, N. Marion, J. Mei, S. P. Nolan, Chem. Eur. J. 2006, 12, 5142;
49. T. Hatakeyama, S. Hashimoto, K. Ishizuka, M. Nakamura, J. Am. Chem. Soc. 2009, 131, 11949;
50. G. Gribble, J. J. Li in Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist (Eds.: J. Baldwin, R. M. Williams, J.-E. Bäckvall), Pergamon, Amsterdam, 2000.
51. Five-membered-ring heteroaryl halides are usually more demanding substrates: L. Salvi, N. R. Davis, S. Z. Ali, S. L. Buchwald, Org. Lett. 2012, 14, 170.
52. Fluorine and Health: Molecular Imaging, Biomedical Materials and Pharmaceuticals (Eds.: A. Tressaud, G. Haufe), Elsevier, Amsterdam, 2008.
53. C. Adamo, V. Barone, J. Chem. Phys. 1999, 110, 6158.
54. Revision A.M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. FoxWallingfordCTGaussian 09, 02, Gaussian, Inc., 2009.
55. F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297.
56. A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 2009, 113, 6378.