Pd-catalyzed oxidative coupling of monosubstituted sydnones and terminal alkynes

Tetrahedron Letters

Volumn 52, Issue 29, 2011, Pages 3797-3801

  Wu, Chunrui ^a   Li, Pan ^a   Fang, Yuesi ^b   Zhao, Jingjing ^a   Xue, Weichao ^a   Li, Yang ^a   Larock, Richard C ^b   Shi, Feng ^a  

^a HENAN UNIVERSITY   (China)

^b IOWA STATE UNIVERSITY   (United States)

Author keywords

C H functionalization; Cross coupling; Pd catalysis; Sydnone

Indexed keywords

4 ALKYNYLSYDNONE DERIVATIVE; ALKYNE; PALLADIUM; SYDNONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CROSS COUPLING REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 79959195498     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.058     Document Type: Article

References (70)

1. For excellent reviews of sydnones, see: (a) Browne, D. L.; Harrity, J. P. A. Tetrahedron 2010, 66, 553;
2. (b) Stewart, F. H. C. Chem. Rev. 1964, 64, 129;
3. (c) Baker, W.; Ollis, W. D. Q. Rev. (London) 1957, 11, 15.
4. (a) Padwa, A. 1, 3-Dipolar Cycloaddition Chemistry; John Wiley & Sons: New York, 1984;
5. (b) Padwa, A.; Pearson, W. H. Synthetic Applications of 1, 3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products; Wiley: New York, Chichester, 2002.
6. Earl, J. C.; Mackney, A. W. J. Chem. Soc. 1935, 899.
7. (a) Brooks, P.; Walker, J. J. Chem. Soc. 1959, 4409;
8. (b) Moustafa, M. A.; Gineinah, M. M.; Nasr, M. N.; Bayoumi, W. A. H. Arch. Pharmacol. 2004, 337, 427.
9. (a) Kier, L. B.; Roche, E. B. J. Pharm. Sci. 1967, 56, 149;
10. (b) Grynberg, N.; Gomes, R.; Shinzato, T.; Echevarria, A.; Miller, J. Anticancer Res. 1992, 12, 1025;
11. (c) Dunkley, C. S.; Thoman, C. J. Bioorg. Med. Chem. Lett. 2003, 13, 2899.
12. (a) Pala, G.; Mantegani, A.; Coppi, G.; Genova, R. Chim. Ther. 1969, 4, 31;
13. (b) Wagner, H.; Hill, J. B. J. Med. Chem. 1974, 17, 1337;
14. (c) Hill, J. B.; Ray, R. E.; Wagner, H.; Aspinall, R. L. J. Med. Chem. 1975, 18, 50.
15. McCaustland, D. J.; Burton, W. H.; Cheng, C. C. J. Heterocycl. Chem. 1971, 8, 89.
16. (a) Dumitraşcu, F.; Mitan, C. I.; Dumitrescu, D.; Drâghici, M. T.; Caproiu, M. T. ARKIVOC 2002, 2, 80;
17. (b) Dumitraşcu, F.; Drâghici, M. T.; Dumitrescu, D.; Tarko, L.; Râileanu, D. Liebigs Ann. 1997, 2613;
18. (c) Turnbull, K.; Ito, S. Synth. Commun. 1996, 26, 1441;
19. (d) Kato, H.; Ohta, M. Bull. Chem. Soc. Jpn. 1962, 35, 1418.
20. (a) Turnbull, K.; George, J. C. Synth. Commun. 1996, 26, 2757;
21. (b) Tien, H.-J.; Yeh, J.-C.; Wu, S.-J. J. Chin. Chem. Soc. 1992, 39, 443;
22. (c) Turnbull, K.; Gross, K. C.; Hall, T. A. Synth. Commun. 1998, 28, 931;
23. (d) Azarifar, D.; Bosra, H. G.; Tajbaksh, M. J. Heterocycl. Chem. 2007, 44, 467.
24. (a) Browne, D. L.; Helm, M. D.; Plant, A.; Harrity, J. P. A. Angew. Chem., Int. Ed. 2007, 46, 8656;
25. (b) Rai, N. S.; Kalluraya, B.; Lingappa, B.; Shenoy, S.; Puranic, V. G. Eur. J. Med. Chem. 2008, 43, 1715;
26. (c) Foster, R. S.; Huang, J.; Vivat, J. F.; Browne, D. L.; Harrity, J. P. A. Org. Biomol. Chem. 2009, 7, 4052;
27. (d) Harju, K.; Vesterinen, J.; Yli-Kauhaluoma, J. Org. Lett. 2009, 11, 2219;
28. (e) Browne, D. L.; Taylor, J. B.; Plant, A.; Harrity, J. P. A. J. Org. Chem. 2010, 75, 984;
29. (f) Browne, D. L.; Vivat, J. F.; Plant, A.; Gomez-Bengoa, E.; Harrity, J. P. A. J. Am. Chem. Soc. 2009, 131, 7762;
30. (g) Browne, D. L.; Taylor, J. B.; Plant, A.; Harrity, J. P. A. J. Org. Chem. 2009, 74, 396.
31. (a) Baker, W.; Ollis, W. D.; Poole, V. D. J. Chem. Soc. 1950, 1542;
32. (b) Thoman, C. J.; Voaden, D. J. Org. Synth. 1965, 45, 96.
33. (a) Applegate, J.; Turnbull, K. Synthesis 1988, 1011;
34. (b) Azarifar, D.; Borsa, H. G. Synthesis 2006, 1123;
35. (c) Azarifar, D.; Borsa, H. G.; Tajbaksh, M.; Habibzadeh, S. Heterocycles 2007, 71, 1815.
36. Wu, C.; Fang, Y.; Larock, R. C.; Shi, F. Org. Lett. 2010, 12, 2234.
37. (a) Rodriguez, A.; Moran, W. J. Synthesis 2009, 650;
38. (b) Rodriguez, A.; Fennessey, R. V.; Moran, W. J. Tetrahedron Lett. 2009, 50, 3942.
39. Cherepanov, I. A.; Bronova, D. D.; Balantseva, E. Y.; Kalinin, V. N. Mendeleev Commun. 1997, 7, 93.
40. Kalinin, V. N.; Min, S. F. J. Organomet. Chem. 1988, 352, C34.
41. Turnbull, K.; Krein, D. M.; Tullis, S. A. Synth. Commun. 2003, 33, 2209.
42. For selected recent accounts and reports, see: (a) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677;
43. (b) Ge, H.; Niphakis, M. J.; Georg, G. I. J. Am. Chem. Soc. 2008, 130, 3708;
44. (c) Peng, C.; Wang, Y.; Wang, J. J. Am. Chem. Soc. 2008, 130, 1556;
45. (d) McDonald, R. I.; Stahl, S. S. Angew. Chem., Int. Ed. 2010, 49, 5529;
46. (e) Rogers, M. M.; Kotov, V.; Chatwichien, J.; Stahl, S. S. Org. Lett. 2007, 9, 4331;
47. (f) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147;
48. (g) Kalyani, D.; Satterfield, A. D.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 8419;
49. (h) Delcamp, J. H.; Brucks, A. P.; White, M. C. J. Am. Chem. Soc. 2008, 130, 11270;
50. (i) Reed, S. A.; Mazzotti, A. R.; White, M. C. J. Am. Chem. Soc. 2009, 131, 11701;
51. (j) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094;
52. (k) Wang, D.-H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315;
53. (l) Liégault, B.; Lee, D.; Huestis, M. P.; Stuart, D. R.; Fagnou, K. J. Org. Chem. 2008, 73, 5022;
54. (m) Yoo, K. S.; O'Neill, J.; Sakaguchi, S.; Giles, R.; Lee, J. H.; Jung, K. W. J. Org. Chem. 2010, 75, 95;
55. (n) Shi, Z.; Ding, S.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 7895;
56. (o) Shi, Z.; Zhang, C.; Li, S.; Pan, D.; Ding, S.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 4572;
57. (p) Shi, Z.; Cui, Y.; Jiao, N. Org. Lett. 2010, 12, 2908;
58. (q) Liu, C.; Jin, L.; Lei, A. Synlett 2010, 2527;
59. (r) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
60. (a) Ye, Z.; Liu, M.; Lin, B.; Wu, H.; Ding, J.; Cheng, J. Tetrahedron Lett. 2009, 50, 530;
61. (b) Yang, L.; Zhao, L.; Li, C.-J. Chem. Commun. 2010, 46, 4184;
62. (c) Chen, M.; Zheng, X.; Li, W.; He, J.; Lei, A. J. Am. Chem. Soc. 2010, 132, 4101;
63. (d) Kim, S. H.; Yoon, J.; Chang, S. Org. Lett. 2011, 13, 1474;
64. For a brief review of oxidative coupling involving terminal alkynes catalyzed by other metals, see: (e) Shao, Z.; Peng, F. Angew. Chem., Int. Ed. 2010, 49, 9566.
65. 3 (M+H) 297.0425, found 297.0422.
66. An N-benzyl variant was also attempted. It resulted in a mixture containing the desired product, but we were not able to purify the product.
67. For reports of the mechanistic details of aerobatic oxidation of Pd(0) to Pd(II), see: (a) Konnick, M. M.; Decharin, N.; Popp, B. V.; Stahl, S. S. Chem. Sci. 2011, 2, 326;
68. (b) Popp, B. V.; Stahl, S. S. Chem. Eur. J. 2009, 15, 2915;
69. (c) Konnick, M. M.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 5753.
70. 14