Synthesis of chiral N-heterocyclic carbene ligands with rigid backbones and application to the palladium-catalyzed enantioselective intramolecular α-arylation of amides

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1666-1669

  Liu, Lantao ^a   Ishida, Naoki ^a   Ashida, Shinji ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79953171936     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200149s     Document Type: Article

References (48)

1. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290
2. Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2239
3. Crudden, C. M.; Allen, D. P. Coord. Chem. Rev. 2004, 248, 2247
4. N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: Weinheim, Germany, 2006.
5. N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Springer: Berlin, Germany, 2007.
6. Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Angew. Chem., Int. Ed. 2007, 46, 2768
7. Würtz, S.; Glorius, F. Acc. Chem. Res. 2008, 41, 1523
8. Diéz-Gonzláez, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612
9. Poyatos, M.; Mata, J. A.; Peris, E. Chem. Rev. 2009, 109, 3677
10. Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 6940
11. For reviews, see: Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951
12. Cesar, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619
13. Snead, D. R.; Seo, H.; Hong, S. Curr. Org. Chem. 2008, 12, 1370 and the references cited therein
14. For recent progress in asymmetric reactions catalyzed by transition metal-NHC complexes, see: Selim, K. B.; Matsumoto, Y.; Yamada, K.; Tomioka, K. Angew. Chem., Int. Ed. 2009, 48, 8733
15. Scarborough, C. C.; Bergant, A.; Sazamaa, G. T.; Guzeia, I. A.; Spencera, L. C.; Stahl, S. S. Tetrahedron 2009, 65, 5084
16. Stenne, B.; Timperio, J.; Savoie, J.; Dudding, T.; Collins, S. K. Org. Lett. 2010, 12, 2032
17. Tiede, S.; Berger, A.; Schlesiger, D.; Rost, D.; Lühl, A.; Blechert, S. Angew. Chem., Int. Ed. 2010, 49, 3972
18. May, T. L.; Dabrowski, J. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2011, 133, 736 and references cited therein
19. Clavier, H.; Correa, A.; Cavallo, L.; Escudero-Adan, E. C.; Benet-Buchholz, J.; Slawin, A. M. Z.; Nolan, S. P. Eur. J. Inorg. Chem. 2009, 1767
20. Ragone, F.; Poater, A.; Cavallo, L. J. Am. Chem. Soc. 2010, 132, 4249
21. Glorius, F.; Altenhoff, G.; Goddard, R.; Lehmann, C. W. Chem. Commun. 2002, 2704
22. Würtz, S.; Lohre, C.; Fröhlich, R.; Bergander, K.; Glorius, F. J. Am. Chem. Soc. 2009, 131, 8344
23. Bexrud, J.; Lautens, M. Org. Lett. 2010, 12, 3160
24. Herrmann, W. A.; Baskakov, D.; Herdtweck, E.; Hoffmann, S. D.; Bunlaksananusorn, T.; Rampf, F.; Rodefeld, L. Organometallics 2006, 25, 2449
25. Cavell, K. J.; Elliott, M. C.; Nielsen, D. J.; Paine, J. S. Dalton Trans. 2006, 4922
26. Baskakov, D.; Herrmann, W. A.; Herdtweck, E.; Hoffmann, S. D. Organometallics 2007, 26, 626
27. Seo, H.; Hirsch-Weil, D.; Abboud, K. A.; Hong, S. J. Org. Chem. 2008, 73, 1983
28. Li, J.; Stewart, I. C.; Grubbs, R. H. Organometallics 2010, 29, 3765
29. For a meso-NHC ligand with a similar skeleton see: Vehlow, K.; Gessler, S.; Blechert, S. Angew. Chem., Int. Ed. 2007, 46, 8082
30. See Supporting Information for experimental details.
31. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805
32. The coupling reaction of diamine 10 with bulkier bromobenzenes such as 2-bromobiphenyl and 2- tert -butylbromobenzene failed to give the corresponding diarylated diamines.
33. The palladium-NHC complexes were synthesized from various Pd(II) precursors with the chiral imidazolidinium salt 6; however, recrystalization of the complexes failed to afford the single crystals suitable for X-ray crystallographic analysis.
34. CCDC-802011 (13) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data-request/cif.
35. Díez-González, S.; Stevens, E. D.; Scott, N. M.; Petersen, J. L.; Nolan, S. P. Chem.-Eur. J. 2008, 14, 158
36. bur value of the new NHC was calculated by SambVca with the standard parameters: radius of sphere 3.5 Å, distance from sphere 2.1 Å, mesh step 0.05 Å. Poater, A.; Cosenza, B.; Correa, A.; Giusdice, S.; Ragone, F.; Scarano, V.; Cavallo, L. Eur. J. Inorg. Chem. 2009, 1559
37. Clavier, H.; Nolan, S. P. Chem. Commun. 2010, 841
38. For the reviews of α-arylation reactions, see: Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082
39. Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010, 49, 676
40. For a review of asymmetric synthesis of oxindoles bearing a tetrasubstituted stereocenter, see: Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381
41. Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402
42. Arao, T.; Kondo, K.; Aoyama, T. Chem. Pharm. Bull. 2006, 54, 1743
43. Luan, X.; Mariz, R.; Robert, C.; Gatti, M.; Blumentritt, S.; Dorta, R. Org. Lett. 2008, 10, 5569
44. Luan, X.; Wu, L.; Drinkel, E.; Mariz, R.; Gatti, M.; Dorta, R. Org. Lett. 2010, 12, 1912
45. Kündig, E. P.; Seidel, T. M.; Jia, Y.-X.; Bernardinelli, G. Angew. Chem., Int. Ed. 2007, 46, 8484
46. Jia, Y.-X.; Hillgren, J. M.; Watsonm, E. L.; Marsden, S. P.; Kündig, E. P. Chem. Commun. 2008, 4040
47. Jia, Y.-X.; Katayev, D.; Bernardinelli, G.; Seidel, T. M.; Kündig, E. P. Chem.-Eur. J. 2010, 16, 6300
48. No reaction was observed with aryl chloride 16 even at higher temperature and in other solvents such as dioxane and toluene.