Grignard allylic substitution reaction catalyzed by 1,2,3-triazol-5-ylidene magnesium complexes

Tetrahedron Letters

Volumn 54, Issue 11, 2013, Pages 1360-1363

  Nomura, Ryosuke ^a   Tsuchiya, Yuji ^a   Ishikawa, Hiroyuki ^a   Okamoto, Sentaro ^a  

^a KANAGAWA UNIVERSITY   (Japan)

Author keywords

12,3 Triazol 5 ylidene; Allylic substitution; Grignard reagent

Indexed keywords

1,2,3 TRIAZOL 5 YLIDENE MAGNESIUM DERIVATIVE; ALKENE DERIVATIVE; ALKYL GROUP; ALLYL COMPOUND; CHLORIDE; GRIGNARD REAGENT; MAGNESIUM DERIVATIVE; ORGANOMETALLIC COMPOUND; PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; GRIGNARD REACTION; SUBSTITUTION REACTION;

EID: 84874944097     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.12.124     Document Type: Article

References (57)

1. Ehlers, A. W.; van Klink, G. P. M.; van Eis, M. J.; Bickelhaupt, F.; Nederkoorn, P. H. J.; Lammertsma, K. J. Mol. Model. 2000, 6, 186
2. Kneisel, F. F.; Dochnahl, M.; Knochel, P. Angew. Chem., Int. Ed. 2004, 1017, 43
3. Gong, L.-Z.; Knochel, P. Synlett 2005, 267
4. Kneisel, F. F.; Leuser, H.; Knochel, P. Synthesis 2005, 2625
5. Ren, H.; Krasovskiy, A.; Knochel, P. Org. Lett. 2004, 6, 4215
6. Liu, C.-Y.; Knochel, P. Org. Lett. 2005, 7, 2543
7. Liu, C.-Y.; Ren, H.; Knochel, P. Org. Lett. 2006, 8, 617
8. Boudet, N.; Lachs, J. R.; Knochel, P. Org. Lett. 2007, 9, 5525
9. Shi, L.; Chu, Y.; Knochel, P.; Mayr, H. J. Org. Chem. 2009, 74, 2760
10. Shi, L.; Chu, Y.; Knochel, P.; Mayr, H. Org. Lett. 2009, 11, 3502.
11. Apsimon, J.; Colier, T. L. Tetrahedron 1986, 42, 5157
12. Tomioka, K. Synthesis 1990, 541
13. Akiyama, T.; Shimizu, M.; Mukaiyama, T. Chem. Lett. 1984, 611
14. Nakajima, M.; Tomioka, T.; Koga, K. Tetrahedron 1993, 49, 9735
15. Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 9751
16. Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
17. Denmark, S. E.; Beutner, G. L.; Wynn, T.; Eastgate, M. D. J. Am. Chem. Soc. 2005, 127, 3774.
18. Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129
19. Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763.
20. Arduengo, A. J. Acc. Chem. Res. 1999, 32, 913
21. Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39
22. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290
23. Carbene Chemistry. From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Marcel Dekker: New York, 2002.
24. Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534
25. Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2239
26. Scott, N. M.; Nolan, S. P. Eur. J. Inorg. Chem. 1815, 2005
27. Hahn, F. E. Angew. Chem., Int. Ed. 2006, 45, 1348
28. N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: Weinheim, Germany, 2006
29. Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122.
30. Lee, Y.; Hoveyda, A. H. J. Am. Chem. Soc. 2006, 128, 15604.
31. Kobayashi, K.; Ueno, M.; Naka, H.; Kondo, Y. Chem. Commun. 2008, 3780
32. Ueno, M.; Wheatley, A. E. H.; Kondo, Y. Chem. Commun. 2006, 3549.
33. Jackowski, O.; Alexakis, A. Angew. Chem., Int. Ed. 2010, 49, 3346
34. Grassi, D.; Alexakis, A. Org. Lett. 2012, 14, 1568
35. Grassi, D.; Li, H.; Alexakis, A. Chem. Commun. 2012, 48, 11404.
36. Okamoto, S.; Ishikaw, H.; Shibata, Y.; Suhara, Y. Tetrahedron Lett. 2010, 51, 5704.
37. Albrecht, M. Chem. Commun. 2008, 3601
38. Mathew, P.; Neels, A.; Albrecht, M. J. Am. Chem. Soc. 2008, 130, 13534
39. Schuster, O.; Yang, L.; Raubenheimer, H. G.; Albrecht, M. Chem. Rev. 2009, 109, 3445
40. Guisado-Barrios, G.; Bouffard, J.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2010, 49, 4759.
41. Chianese, A. R.; Li, X. W.; Janzen, M. C.; Faller, J. W.; Crabtree, R. H. Organometallics 2003, 22, 1663
42. Heckenroth, M.; Neels, A.; Garnier, M. G.; Aebi, P.; Ehlers, A. W.; Albrecht, M. Chem. Eur. J. 2009, 15, 9375
43. Yang, L.; Kruger, A.; Neels, A.; Albrecht, M. Organometallics 2008, 27, 3161.
44. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 565
45. Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952
46. Finn, M. G.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1231.
47. Karthikeyan, T.; Sankararaman, S. Tetrahedron Lett. 2009, 50, 5834
48. Lalrempuia, R.; McDaniel, N. D.; Müller-Bunz, H.; Bernhard, S.; Albrecht, M. Angew. Chem., Int. Ed. 2010, 49, 9765
49. Nakamura, T.; Ogata, K.; Kukuzawa, S. Chem. Lett. 2010, 39, 920
50. Kilpin, K. J.; Paul, U. S. D.; Lee, A.-L.; Crowley, J. D. Chem. Commun. 2011, 47, 328
51. Nakamura, T.; Terashima, T.; Ogata, K.; Fukuzawa, S. Org. Lett. 2011, 13, 620
52. Saravanakuman, R.; Ramkumar, V.; Sankararaman, S. Organometallics 2011, 30, 1689
53. Prades, A.; Peris, E.; Albrecht, M. Organometallics 2011, 30, 1162
54. Bouffard, J.; Keitz, B. K.; Tonner, R.; Guisado-Barrios, G.; Frenking, G.; Grubbs, R. H.; Bertrand, G. Organometallics 2011, 30, 2617
55. Bernet, L.; Lalrempuia, R.; Ghattas, W.; Mueller-Bunz, H.; Vigara, L.; Llobet, A.; Albrecht, M. Chem. Commun. 2011, 47, 8058.
56. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057
57. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.