Palladium-catalyzed amination of aryl mesylates

Angewandte Chemie - International Edition

Volumn 47, Issue 34, 2008, Pages 6402-6406

  So, Chau Ming ^a   Zhou, Zhongyuan ^a   Lau, Chak Po ^a   Kwong, Fuk Yee ^a  

^a HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

Amination; Cross coupling; Mesylates; Palladium; Phosphanes

Indexed keywords

AMINES; CHEMICAL REACTIONS; PALLADIUM; PHOSPHORUS COMPOUNDS;

CHEMICAL EQUATIONS; CROSS-COUPLING; MESYLATES; PALLADIUM-CATALYZED AMINATION; PD(OAC)2; PHOSPHANES; PHOSPHINE LIGANDS;

AMINATION;

LIGAND; MESYLIC ACID DERIVATIVE; NITROGEN; PALLADIUM; PHOSPHINE; PHOSPHINE DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CHEMISTRY;

AMINATION; CATALYSIS; LIGANDS; MESYLATES; NITROGEN; PALLADIUM; PHOSPHINES;

EID: 52049100455     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802157     Document Type: Article

References (56)

1. a) A. O. King, N. Yasuda in Organometallics in Process Chemistry (Ed.: R. D. Larsen), Springer, Berlin, 2004, pp. 205-246, and references therein;
2. b) S. A. Lawrence, Amines, Synthesis Properties, and Application; Cambridge University Press, Cambridge, 2004.
3. For early report on catalytic amination, see: a) M. Kosugi, M. Kameyama, T. Migita, Chem. Lett. 1983, 927.
4. For early reports on Buchwald-Hartwig amination, see: b) A. S. Guram, R. A. Rennels, S. L. Buchwald, Angew. Chem. 1995, 107, 1456;
5. Angew. Chem. Int. Ed. Engl. 1995, 34, 1348;
6. c) J. Louie, J. F. Hartwig, Tetrahedron Lett. 1995, 36, 3609.
7. For selected reviews: see: a) A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 219, 131;
8. b) J. F. Hartwig in Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), Wiley-Interscience, New York, 2002;
9. c) L. Jiang, S. L. Buchwald in Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. (Eds.: A. de Meijere, F. Diederich), Wiley, Weinheim, 2004.
10. a) M. Nishiyama, T. Yamamoto, Y. Koie, Tetrahedron Lett. 1998, 39, 617;
11. b) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295.
12. F. Rataboul, A. Zapf, R. Jackstell, S. Harkal, T. Riermeier, A. Monsees, U. Dingerdissen, M. Beller, Chem. Eur. J. 2004, 10, 2983.
13. J. P. Wolfe, H. Tomori, J. P. Sadighi, J. Yin, S. L. Buchwald, J. Org. Chem. 2000, 65, 1158.
14. N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553.
15. a) S. Urgaonkar, J.-H. Xu, J. G. Verkade, J. Org. Chem. 2003, 68, 8416;
16. b) C. V. Reddy, J. V. Kingston, J. G. Verkade, J. Org. Chem. 2008, 73, ASAP.
17. For a review on aryl chloride couplings, see: A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350;
18. Angew. Chem. Int. Ed. 2002, 41, 4176.
19. For recent review on the development and application of bulky electron-rich phosphines for palladium-catalyzed cross-coupling reaction of aryl halides and sulfonates, see: A. Zapf, M. Beller, Chem. Commun. 2005, 431 and references therein.
20. For Suzuki coupling, see: a) H. N. Nguyen, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 11818;
21. for Buchwald-Hartwig C-N bond coupling, see: b) X. Huang, K. W. Anderson, D. Zim, L. Jiang, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 6653;
22. for Sonogashira coupling using activated ArOTs, see: c) D. Gelman, S. L. Buchwald, Angew. Chem. 2003, 115, 6175;
23. Angew. Chem. Int. Ed. 2003, 42, 5993;.
24. For ArOTs substrates, for Kumada couplings, see: a) A. H. Roy, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 8704;
25. b) M. E. Limmert, A. H. Roy, J. F. Hartwig, J. Org. Chem. 2005, 70, 9364;
26. c) L. Ackermann, A. Althammer, Org. Lett. 2006, 8, 3457;
27. for amination, see d) B. C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1998, 120, 7369;
28. for C-S bond formation (one substrate example), see: e) M. A. FernOndez-RodrPguez, Q. Shen, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 2180;
29. for Suzuki coupling, see: f) L. Zhang, T. Meng, J. Wu, J. Org. Chem. 2007, 72, 9346.
30. For alkenyl OTs substrates, Suzuki coupling, see: g) D. Steinhuebel, J. M. Baxter, M. Palucki, I. W. Davies, J. Org. Chem. 2005, 70, 10124;
31. for Buchwald-Hartwig amidation, see: h) A. Klapars, K. R. Campos, C.-y. Chen, R. P. Volante, Org. Lett. 2005, 7, 1185;
32. for Heck coupling, see: i) A. L. Hansen, T. Skrydstrup, Org. Lett. 2005, 7, 5585;
33. j) A. L. Hansen, J.-P. Ebran, M. Ahlquist, P.-O. Norrby, T. Skrydstrup, Angew. Chem. 2006, 118, 3427;
34. Angew. Chem. Int. Ed. 2006, 45, 3349.
35. Aryl mesylate couplings have rarely been studied, only nickel-catalyzed C-C bond couplings have been reported, see: a) V. Percec, G. M. Golding, J. Smidrkal, O. Weichold, J. Org. Chem. 2004, 69, 3447;
36. b) V. Percec, J.-Y. Bae, D. H. Hill, J. Org. Chem. 1995, 60, 1060;
37. c) V. Percec, J.-Y. Bae, D. H. Hill, J. Org. Chem. 1995, 60, 1066;
38. d) V. Percec, J.-Y. Bae, D. H. Hill, J. Org. Chem. 1995, 60, 6895;
39. e) M. Ueda, A. Saitoh, S. Oh-tani, N. Miyaura, Tetrahedron 1998, 54, 13079;
40. f) Y. Kobayashi, R. Mizojiri, Tetrahedron Lett. 1996, 37, 8531.
41. For descriptions of atom economy, see: B. M. Trost, Angew. Chem. 1995, 107, 285;
42. Angew. Chem. Int. Ed. Engl. 1995, 34, 259.
43. a = -14.9). Ionization Constants of Organic Acidsin Solution (Eds.: E. P. Serjeant, B. Dempsey), Pergamon, Oxford, UK, 1979 (IUPAC Chemical Data Series No. 23).
44. C. M. So, C. P. Lau, F. Y. Kwong, Org. Lett. 2007, 9, 2795.
45. R. H. Munday, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 2754.
46. 4OTs instead of the corresponding mesylate, the reaction proceeded faster and ran to completion within 3 h, giving the isolated product in >95% yield.
47. See Supporting Information for initial screening details.
48. a) C. J. Li, T. H. Chan, Organic Reactionsin Aqueous Media, Wiley, New York, 1997;
49. b) Aqueous-Phase Organometallic Catalysis (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 1998;
50. c) U. M. Lindström, Chem. Rev. 2002, 102, 2751.
51. For selected examples, see: A. A. Danopoulos, N. Tsoureas, S. A. Macgregor, C. Smith, Organometallics 2007, 26, 253.
52. a) J. Cámpora, E. Gutierrez Puebla, J. A. Lopez, A. Monge, P. Palma, D. Del Rio, E. Carmona, Angew. Chem. 2001, 113, 3753;
53. Angew. Chem. Int. Ed. 2001, 40, 3641;
54. b) T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685.
55. For a seminal work on MAP-type ligands, see: c) P. Koçovský , S. Vyskoèil, I. Cisaøová, J. Sejbal, I. Tislerova, M. Smrcina, G. C. Lloyd-Jones, S. C. Stephen, C. P. Butts, M. Murray, V. Langer, J. Am. Chem. Soc. 1999, 121, 7714.
56. η3(arene)coordination, see: d) U. Christmann, D. A. Pantazis, J. Benet-Buchholz, J. E. McGrady, F. Maseras, R. Vilar, J. Am. Chem. Soc. 2006, 128, 6376.