Room-temperature palladium-catalyzed C-H activation: Ortho-carbonylation of aniline derivatives

Angewandte Chemie - International Edition

Volumn 48, Issue 10, 2009, Pages 1830-1833

  Houlden, Chris E ^a   Hutchby, Marc ^a   Bailey, Chris D ^a   Ford, J Gair ^c   Tyler, Simon N G ^c   Gagné, Michel R ^b   Lloyd Jones, Guy C ^a   Booker Milburn, Kevin I ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF NORTH CAROLINA   (United States)

^c ASTRAZENECA   (United Kingdom)

Author keywords

C h activation; Carbonylation; Heterocycles; Heterogeneous catalysis; Palladium

Indexed keywords

ACTIVATION ANALYSIS; AMINES; CARBONYLATION; CATALYSIS;

ANILINE DERIVATIVES; BENZOQUINONE; C-H ACTIVATION; CYCLIC IMIDES; HETEROCYCLES; HETEROGENEOUS CATALYSIS; HIGH YIELDS; PRECATALYST; ROOM TEMPERATURES;

PALLADIUM;

ANILINE; ANILINE DERIVATIVE; ANTHRANILIC ACID DERIVATIVE; ANTHRANILIC ACID METHYL ESTER; CARBON MONOXIDE; IMIDOESTER; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS; TEMPERATURE;

ANILINE COMPOUNDS; ANTHRANILIC ACIDS; CARBON MONOXIDE; CATALYSIS; IMIDOESTERS; PALLADIUM; TEMPERATURE;

EID: 61349162358     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200805842     Document Type: Article

References (39)

1. a)F. Kakiuchi, T. Kochi, Synthesis 2008, 3013-3039;
2. b) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174-238;
3. c) B. J. Li, S.-D. Yang, Z. J. Shi, Synlett 2008, 949-957;
4. d) L.-C. Campeau, D. R. Stuart, K. Fagnou, Aldrichimica Acta 2007, 40, 35.
5. During the preparation of this manuscript Yu and Giri reported the first palladium(II)-catalyzed or tho carbonylation of benzoic and phenylacetic acids by C-H insertion: R. Giri, J-Q. Yu, J. Am. Chem. Soc. 2008, 130, 14082.
6. C. E. Houlden, C. D. Bailey, J. G. Ford, M. R. Gagne, G. C. Lloyd-Jones, K. I. Booker-Milburn, J. Am. Chem. Soc. 2008, 130, 10066.
7. II-amide complexes, see: H. Horino, N. Inoue, J. Org. Chem. 1981, 46, 4416.
8. For palladium-catalyzed C-H activation reactions with phenyl amides as directing groups, see: a) (vinylation) M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2002,124, 2002;
9. b) J.-R. Wang, C.-T. Yang, L. Liu, Q-X. Guo, Tetrahedron Lett. 2007, 48, 5449;
10. c) (arylation with boronic acids) Z. Shi, B. Li, X. Wan, J. Cheng, Z. Fang, B. Cao, C. Qin, Y. Wang, Angew. Chem. 2007,119, 5650;
11. Angew. Chem. Int. Ed. 2007, 46, 5554;
12. Z. Shi, B. Li, X. Wan, J. Cheng, Z. Fang, B. Cao, C. Qin, Y. Wang, Angew. Chem. 2007, 119, 7874;
13. Angew. Chem. Int. Ed. 2007, 46, 7730 - 7730;
14. d) (arylation without boronic acids) G. Brasche, J. García- Fortanet, S. L. Buchwald, Org. Lett. 2008,10, 2207;
15. e) S. Yang, B. Li, X. Wan, Z. Shi, J. Am. Chem. Soc. 2007,129, 6066;
16. f) O. Daugulis, V. G. Zaitsev, Angew. Chem. 2005, 117, 4114;
17. Angew. Chem. Int. Ed. 2005, 44, 4046;
18. g) B.-J. Li, S.-L. Tian, Z. Fang, Z.-J. Shi, Angew. Chem. 2008, 120, 1131-1134;
19. Angew. Chem. Int. Ed. 2008, 47, 1115-1118;
20. h) (ethoxycarbonylation) W.-Y. Yu, W. N. Sit, K.-M. Lai, Z. Zhou, A. S. C. Chan, J. Am. Chem. Soc. 2008, 130, 3304;
21. i) (chlorination) X. Wan, Z. Ma, B. Li, K. Zhang, S. Cao, S. Zhang, Z. Shi, J. Am. Chem. Soc. 2006, 128, 7416.
22. For CO insertion into palladacycles, see: a) J. Dupont, C. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527;
23. b) A. D. Ryabov, Synthesis 1985, 233.
24. For palladium-catalyzed urea ortho-carbonylation using thallium intermediates, see: a) R. C. Larock, C. A. Fellows, J. Am. Chem. Soc. 1982, 104, 1900;
25. b) A. Krantz, R. W. Spencer, T. F. Tam, T. Liak, US Patent 4,665,070, 1987;
26. c) A. Krantz, R. W. Spencer, T. F. Tam, T. J. Liak, L. J. Copp, E. M. Thomas, S. P. Rafferty, J. Med. Chem. 1990, 33, 464.
27. For the synthesis, biological activity, and reactions of 2-hetero-4H-3,1-benzoxazinones see: G. M. Coppola, J. Heterocycl. Chem. 2000, 37, 1369, and references therein.
28. II/CO has been used for the manufacture of polymers from diols. From NMR studies we suggest that polycarbonate oligomers are formed from hydroquinone repeating units and methanol termini: a) M. Okamoto, J. Sugiyama, T. Yamamoto, J. Appl. Polym. Sci. 2008, 110, 3902;
29. b) K. Okuyama, J. Sugiyama, R. Nagahata, M. Asai, M. Ueda, K. Takeuchi, Macromolecules 2003, 36, 6953.
30. 2 derivative failed to react altogether.
31. 2] precatalyst system for mild and selective C-H activation (Ref. [3]).
32. Pure 8 a was subjected to the reaction conditions from Table 2. After 1.5 hours, all of 8 a was consumed and the ester 10 a was isolated in 95 % yield.
33. For recent reports on synthesis and biological activity of 2,4(1H,3H)-quinazolinediones see: a) Z. Li, H. H. Huang, H. Sun, H. Jiang, H. Liu, J. Comb. Chem. 2008, 10, 484;
34. b) C. Larksarp, H. Alper, J. Org. Chem. 2000, 65, 2773, and references therein.
35. For the formation of quinazolinediones from basic condensation of ortho-ester aryl urea groups, see: E. P. Papadopoulos, C. D. Torres, J. Heterocycl. Chem. 1982, 19, 269.
36. To the best of our knowledge, solvolysis of urea derivatives requires relatively harsh conditions, for example, high temperatures, strongly acidic or basic conditions, metal catalysis etc: a) J. Wang, Q. Li, W. Dong, M. Kang, X. Wang, S. Peng, Appl. Catal. 2004, 261, 191;
37. b) N. V. Kaminskaia, N. M. Kostíc, Inorg. Chem. 1998,37,4302;
38. 2Me 18h, 81% 48h, 100% that phenyldimethyl urea derivatives undergo hydrolysis under acidic or basic conditions via phenylisocyanate intermediates:
39. S. Salvestrini, P. DiCerbo, S. Capasso, J. Chem. Soc. Perkin Trans. 22002, 1889. We propose that the ease with which phenyldiiso-propyl urea derivatives undergo solvolysis may be a result of the leaving group ability of diisopropylamine being enhanced by the steric compression afforded by the isopropyl groups. Further mechanistic investigation is ongoing and will be reported in due course.