Sequential copper(I)-catalyzed reaction of amines with o-acetylenyl- substituted phenyldiazoacetates

Advanced Synthesis and Catalysis

Volumn 350, Issue 14-15, 2008, Pages 2359-2364

  Peng, Cheng ^a,b   Cheng, Jiajia ^a,b   Wang, Jianbo ^a,b  

^a PEKING UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

Alkynes; Carbenoids; Copper; Diazo compounds; Homogeneous catalysis; Insertion

Indexed keywords

EID: 55049097647     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800249     Document Type: Article

References (63)

1. For recent reviews of tandem catalysis, see: a) R. A. Bunce, Tetrahedron 1995, 51, 13103;
2. b) P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195;
3. c) D. E. Fogg, E. N. dos Santos, Coord. Chem. Rev. 2004, 248, 2365;
4. d) J. C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001;
5. e) A. Ajamian, J. L. Gleason, Angew. Chem. Int. Ed. 2004, 43, 3754.
6. J. Louie, C. W. Bielawski, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 11312.
7. P. A. Evans, J. E. Robinson, J. Am. Chem. Soc. 2001, 123, 4609.
8. B. Mariampillai, D. Alberico, V. Bidau, M. Lautens, J. Am. Chem. Soc. 2006, 128, 14436.
9. For reviews, see: a) M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley-Interscience, New York, 1998;
10. b) T. Ye, M. A. McKervey, Chem. Rev. 1994, 94, 1091.
11. For selected recent examples of metal carbene N-H insertions, see: a) S. H. Lee, K. Yoshida, H. Matsushita, B. Clapham, G. Koch, J. Zimmermann, K. D. Janda, J. Org. Chem. 2004, 69, 8829;
12. b) J. R. Davies, P. D. Kane, C. J. Moody, J. Org. Chem. 2005, 70, 7305;
13. c) F. A. Davis, H. Xu, Y. Wu, J. Zhang, Org. Lett. 2006, 8, 2273.
14. For recent reviews, see: a) A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 219, 131;
15. b) J. F. Hartwig, in: Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.: E. Negishi), Wiley-Interscience, New York, 2002, p 1051;
16. c) T. E. MRller, M. Beller, Chem. Rev. 1998, 98, 675;
17. d) F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079;
18. e) F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104;
19. f) M. Nobis, B. Drießen-Hölscher, Angew. Chem. Int. Ed. 2001, 40, 3983;
20. g) M. Beller, J. Seayad, A. Tillack, H. Jiao, Angew. Chem. Int. Ed. 2004, 43, 3368;
21. h) S. Hong, T. J. Marks, Acc. Chem. Res. 2004, 37, 673.
22. a) E. Haak, I. Bytschkov, S. Doye, Angew. Chem. Int. Ed. 1999, 38, 3389;
23. b) E. Haak, H. Siebeneicher, S. Doye, Org. Lett. 2000, 2, 1935;
24. c) F. Pohlki, S. Doye, Angew. Chem. Int. Ed. 2001, 40, 2305;
25. d) J. S. Johnson, R. G. Bergman, J. Am. Chem. Soc. 2001, 123, 2923;
26. e) B. F. Straub, R. G. Bergman, Angew. Chem. Int. Ed. 2001, 40, 4632;
27. f) Y. Shi, J. T. Ciszewski, A. L. Odom, Organometallics 2001, 20, 3967;
28. g) C. Cao, J. T. Ciszewski, A. L. Odom, Organometallics 2001, 20, 5011;
29. h) C. Cao, Y. Shi, A. L. Odom, Org. Lett. 2002, 4, 2853;
30. i) A. Tillack, I. G. Castro, C. G. Hartung, M. Beller, Angew. Chem. Int. Ed. 2002, 41, 2541;
31. j) I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2003, 6, 935;
32. k) Y. Shi, Y. Li, A. L. Odom, J. Am. Chem. Soc. 2004, 126, 1794;
33. l) C. Lorber, R. Choukroun, L. Vendier, Organometallics 2004, 23, 1845.
34. a) I. Kadota, A. Shibuya, L. M. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570;
35. b) T. Shimada, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12670;
36. c) G. B. Bajracharya, Z. Huo, Y. Yamamoto, J. Org. Chem. 2005, 70, 4883.
37. J. J. Brunet, N. C. Chu, O. Diallo, S. Vincendeau, J. Mol. Catal. A: Chem. 2005, 240, 245.
38. a) M. Tokunaga, M. Eckert, Y. Wakatsuki, Angew. Chem. Int. Ed. 1999, 38, 3222;
39. b) Y. Uchimaru, Chem. Commun. 1999, 1133.
40. For recent reviews, see: a) R. A. Widenhoefer, X. Han, Eur. J. Org. Chem. 2006, 4555;
41. b) N. T. Patil, Y. Yamamoto, Arkivoc 2007, x, 121;
42. for recent reports, see: c) D. Kadzimirsz, D. Hildebrandt, K. Merz, G. Dyker, Chem. Commun. 2006, 661;
43. d) E. Mizushima, T. Hayashi, M. Tanaka, Org. Lett. 2003, 5, 3349.
44. a) C. G. Hartung, A. Tillack, H. Trauthwein, M. Beller, J. Org. Chem. 2001, 66, 6339;
45. b) M. Beller, C. M. Breindl Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002,1579.
46. X. Li, A. Chianese, Y. Vogel, R. H. Crabtree, Org. Lett. 2005, 7, 5437.
47. a) Y. Li, T. J. Marks, Organometallics 1996, 15, 3770;
48. b) Y. Li, T. J. Marks, J. Am. Chem. Soc. 1998, 120, 1757;
49. c) J. S. Ryu, G. Y. Li, T. J. Marks, J. Am. Chem. Soc. 2003, 125, 12584.
50. a) C. W. Kruse, R. F. Kleinschmidt, J. Am. Chem. Soc. 1961, 83, 213;
51. b) C. W. Kruse, R. F. Kleinschmidt, J. Am. Chem. Soc. 1961, 83, 216.
52. a) J. Barluenga, F. Aznar, R. Liz, R. Rodes, J. Chem. Soc. Perkin Trans. 1 1980, 2732;
53. b) J. Barluenga, F. Aznar, Synthesis 1977, 195.
54. a) P. J. Walsh, A. M. Baranger, R. G. Bergman, J. Am. Chem. Soc. 1992, 114, 1708;
55. b) A. M. Baranger, P. J. Walsh, R. G. Bergman, J. Am. Chem. Soc. 1993, 115, 2753.
56. a) A. Haskel, T. Straub, M. S. Eisen, Organometallics 1996, 15, 3773;
57. b) T. Straub, A. Haskel, T. G. Neyroud, M. Kapon, M. Botoshansky, M. S. Eisen, Organometallics 2001, 20, 5017.
58. a) L. Xu, I. R. Lewis, S. K. Davidsen, J. B. Summers, Tetrahedron Lett. 1998, 39, 5159;
59. b) T. E. Müller, M. Grosche, E. Herdtweck, A. K. Pleier, E. Walter, Y. K. Yan, Organometallics 2000, 19, 170.
60. CCDC 692612 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
61. Very recently, Wu and co-workers have reported selective synthesis of isoindole and dihydroisoquinoline derivatives by using different transition metal catalysts, see: Q. Ding, Y. Ye, R. Fan, J. Wu, J. Org. Chem. 2007, 72, 5439.
62. For recent reports on the synthesis and application of isoindole derivatives, see: a) N. Dieltiens, C. V. Stevens, Org. Lett. 2007, 9, 465;
63. b) T. Mitsumori, M. Bendikov, O. Dautel, F. Wudl, T. Shioya, H. Sato, Y. Sato, J. Am. Chem. Soc. 2004, 126, 16793.