Carbohydrate-containing N-heterocyclic carbene complexes

Journal of Organometallic Chemistry

Volumn 692, Issue 21, 2007, Pages 4593-4602

  Tewes, Friederike ^a   Schlecker, Andreas ^a   Harms, Klaus ^a   Glorius, Frank ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Carbohydrates; Catalysis; N Heterocyclic carbenes; Palladium complex; Silver complex

Indexed keywords

ALDEHYDES; CARBOHYDRATES; CATALYSTS; COMPLEXATION; METAL COMPLEXES; MOLECULAR STRUCTURE; PALLADIUM COMPOUNDS; SILVER COMPOUNDS; SYNTHESIS (CHEMICAL);

HETEROCYCLIC CARBENE COMPLEXES; PALLADIUM COMPLEX; SILVER COMPLEX;

OLEFINS;

EID: 34548526297     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2007.05.007     Document Type: Article

References (78)

1. Lindhorst T.K. Chem. Unserer Zeit 34 (2000) 38
2. Nelson D.L., and Cox M.M. Lehninger Principles of Biochemistry (2004), Palgrave Macmillan
3. Liu X.Y., Stocker B.L., and Seeberger P.H. J. Am. Chem. Soc. 128 (2006) 3638 and references cited therein
4. Kunz H. Pure Appl. Chem. 67 (1995) 1627
5. For a review, see:. Gnas Y., and Glorius F. Synthesis 12 (2006) 1899 and references cited therein
6. Klegraf E., Knauer S., and Kunz H. Angew. Chem., Int. Ed. 45 (2006) 2623 and references cited therein
7. Park H., and RajanBabu T.V. J. Am. Chem. Soc. 124 (2002) 734
8. Brunner H., Schönherr M., and Zabel M. Tetrahedron: Asymmetry 2 (2001) 2671
9. Castillón S., Claver C., and Di{dotless}́az Y. Chem. Soc. Rev. 34 (2005) 702
10. Khiar N., Suárez B., Stiller M., Valdivia V., and Fernández I. Phosphorus Sulfur Silicon 180 (2005) 1253
11. RajanBabu T.V., and Casalnuovo A.L. Pure Appl. Chem. 66 (1994) 1535
12. For a carbohydrate derived organocatalyst, see:. Becker C., Hoben C., and Kunz H. Adv. Synth. Catal. 349 (2007) 417
13. Taylor M.S., and Jacobsen E.N. Angew. Chem., Int. Ed. 45 (2006) 1520 and references cited therein
14. Arduengo III A.J., Harlow R.L., and Kline M. J. Am. Chem. Soc. 113 (1991) 361
15. See also:. Igau A., Grützmacher H., Baceiredo A., and Bertrand G. J. Am. Chem. Soc. 110 (1988) 6463
16. Reviews on NHC:. Herrmann W.A. Angew. Chem., Int. Ed. 41 (2002) 1291
17. In: Nolan S.P. (Ed). N-Heterocyclic Carbenes in Synthesis (2006), Wiley-VCH
18. In: Glorius F. (Ed). N-Heterocyclic Carbenes in Transition Metal Catalysis (2006), Springer
19. Cavell K.J., and McGuinness D.S. Coord. Chem. Rev. 248 (2004) 671
20. Peris E., and Crabtree R.H. Coord. Chem. Rev. 248 (2004) 2239
21. Hillier A.C., Grasa G.A., Viciu M.S., Lee H.M., Yang C.L., and Nolan S.P. J. Organomet. Chem. 653 (2002) 69
22. Bourissou O., Guerret O., Gabbaï F.P., and Bertrand G. Chem. Rev. 100 (2000) 39
23. Arduengo III A.J. Acc. Chem. Res. 32 (1999) 913
24. Herrmann W.A., Elison M., Fischer J., Köcher C., and Artus G.R.J. Angew. Chem., Int. Ed. 34 (1995) 2371
25. Lee M.-T., Lee H.M., and Hu C.-H. Organometallics 26 (2007) 1317
26. Kremzow D., Seidel G., Lehmann C.W., and Fürstner A. Chem. Eur. J. 11 (2005) 1833
27. For recent publications, see. Gonzalez-Bobes F., and Fu G.C. J. Am. Chem. Soc. 128 (2006) 5360
28. Marion N., Navarro O., Mei J., Stevens E.D., Scott N.M., and Nolan S.P. J. Am. Chem. Soc. 128 (2006) 4101
29. Altenhoff G., Goddard R., Lehmann C.W., and Glorius F. Angew. Chem., Int. Ed. 42 (2003) 3690
30. Altenhoff G., Goddard R., Lehmann C.W., and Glorius F. J. Am. Chem. Soc. 126 (2004) 15195 and references cited therein
31. for reviews, see. Bellina F., Carpita A., and Rossi R. Synthesis 15 (2004) 2419
32. Miyaura N. In: Diederich F., and de Meijere A. (Eds). Metal-catalyzed Cross-coupling Reaction (2004), Wiley-VCH, New York (Chapter 2)
33. Miyaura N. Top. Curr. Chem. 219 (2002) 11
34. Grasa G.A., and Nolan S.P. Org. Lett. 3 (2001) 119
35. Eckhardt M., and Fu G.C. J. Am. Chem. Soc. 125 (2003) 13642
36. Altenhoff G., Würtz S., and Glorius F. Tetrahedron Lett. 47 (2006) 2925
37. Grubbs R.H. Angew. Chem., Int. Ed. 45 (2006) 3760
38. Despagnet-Ayoub E., and Ritter T. In: Glorius F. (Ed). N-Heterocyclic Carbenes in Transition Metal Catalysis (2006), Springer 193 and references cited therein
39. For a review, see. Grasa G.A., Singh R., and Nolan S.P. Synthesis (2004) 971
40. For carbene-catalyzed transesterifications, see:. Grasa G.A., Kissling R.M., and Nolan S.P. Org. Lett. 4 (2002) 3583
41. Nyce G.W., Lamboy J.A., Connor E.F., Waymouth R.M., and Hedrick J.L. Org. Lett. 4 (2002) 3587
42. Grasa G.A., Güveli T., Singh R., and Nolan S.P. J. Org. Chem. 68 (2003) 2812
43. Connor E.F., Nyce G.W., Myers M., Moeck A., and Hendrick J.L. J. Am. Chem. Soc. 124 (2002) 914
44. Nyce G.W., Glauser T., Connor E.F., Moeck A., Waymouth R.M., and Hedrick J.L. J. Am. Chem. Soc. 125 (2003) 3046
45. Singh R., Kissling R.M., Letellier M.-A., and Nolan S.P. J. Org. Chem. 69 (2004) 209
46. Burstein C., and Glorius F. Angew. Chem., Int. Ed. 43 (2004) 6205
47. Burstein C., Tschan S., Xie X., and Glorius F. Synthesis (2006) 2418
48. Schrader W., Handayani P.P., Burstein C., and Glorius F. Chem. Commun. (2007) 716
49. Sohn S.S., Rosen E.L., and Bode J.W. J. Am. Chem. Soc. 126 (2004) 14370
50. He M., and Bode J.W. Org. Lett. 7 (2005) 3131
51. Sohn S.S., and Bode J.W. Org. Lett. 7 (2005) 3873
52. See also:. Chow K.Y.-K., and Bode J.W. J. Am. Chem. Soc. 126 (2004) 8126
53. Reynolds N.T., Read de Alaniz J., and Rovis T. J. Am. Chem. Soc. 126 (2004) 9518
54. Chan A., and Scheidt K.A. Org. Lett. 7 (2005) 905
55. Reynolds N.T., and Rovis T. J. Am. Chem. Soc. 127 (2005) 16406
56. Zeitler K. Org. Lett. 8 (2006) 637
57. Nair V., Vellalath S., Poonoth M., Mohan R., and Suresh E. Org. Lett. 8 (2006) 507
58. Nair V., Vellalath S., Poonoth M., and Suresh E. J. Am. Chem. Soc. 128 (2006) 8736
59. He M., Struble J.R., and Bode J.W. J. Am. Chem. Soc. 128 (2006) 8418
60. Fischer C., Smith S.W., Powell D.A., and Fu G.C. J. Am. Chem. Soc. 128 (2006) 1472
61. Chiang P.-C., Kaeobamrung J., and Bode J.W. J. Am. Chem. Soc. 129 (2007) 3520
62. Phillips E.M., Wadamoto M., Chan A., and Scheidt K.A. Angew. Chem., Int. Ed. 46 (2007) 3107
63. Diploma Work A. Schlecker, Marburg, 2005.
64. Diploma Work F. Tewes, Marburg, 2006.
65. F. Glorius, DE 102004060247/2004.
66. In parallel to the preparation of this manuscript, a related report appeared:. Nishioka T., Shibata T., and Kinoshita I. Organometallics 26 (2007) 1126
67. Grimmet M.R. Imidazole and Benzimidazole Synthesis (1997), Academic Press, San Diego
68. Al Mourabit A., Beckmann M., Poupat C., Ahond A., and Potier P. Tetrahedron: Asymmetry 7 (1996) 3455
69. Vashishtha S.C., Hawes E.M., McKay G., and McCann D.J. Drug Metab. Dispos. 28 (2000) 1009
70. Miyake T., Tsuchiya T., Umezawa S., Saito S., and Umezawa H. Bull. Chem. Soc. Jpn. 59 (1986) 1387
71. Mitchell S.A., Pratt M.R., Hruby V.J., and Polt R. J. Org. Chem. 66 (2001) 2327
72. Nie X., and Wang G. J. Org. Chem. 70 (2005) 8687
73. The identity of the counteranion of imidazolium salts 6a and 6b was not unequivocally determined.
74. This is a well known trapping reaction for NHC. See for example: Ref. [7b].
75. Garrison J.C., and Youngs W.J. Chem. Rev. 105 (2005) 3978
76. Wang H.M.J., and Lin I.J.B. Organometallics 17 (1998) 972
77. Mori K., and Qian Z.H. Bull. Soc. Chim. Fr. 130 (1993) 382
78. Bay S., Huteau V., Zarantonelli M.L., Pires R., Ughetto-Monfrin J., Taha M.K., England P., and Lafaye P. J. Med. Chem. 47 (2004) 3916