Bidentate Lewis acids as catalysts for the activation of 1,2-diazenes in organic synthesis

Synlett

Volumn 23, Issue 5, 2012, Pages 699-705

  Wegner, Hermann A ^a   Kessler, Simon N ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

arenes; boron; catalysis; Diels Alder reaction; Lewis acids

Indexed keywords

1,2 DIAZENE DERIVATIVE; ALCOHOL; AROMATIC COMPOUND; BENZENE DERIVATIVE; CHEMICAL COMPOUND; DIENOPHILE DERIVATIVE; ENAMINE; ENOL DERIVATIVE; LEWIS ACID; LEWIS BASE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CATALYST; CHEMICAL BINDING; CHEMICAL INTERACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONCEPTUAL FRAMEWORK; CYCLOADDITION; DIELS ALDER REACTION; HYDROGEN BOND; INVERSE ELECTRON DEMAND DIELS ALDER REACTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84858073756     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290132     Document Type: Article

References (51)

1. Metal-Catalyzed Cross-Coupling Reactions 2nd ed. de Meijere A Diederich F Wiley-VCH Weinheim 2004
2. Handbook of Metathesis Grubbs R H. Wiley-VCH Weinheim 2003
3. Metathesis in Natural Product Synthesis. Strategies, Substrates and Catalysts; Cossy J., Arseniyadis S., Meyer C.; Wiley-VCH: Weinheim, 2011
4. Lewis Acids in Organic Synthesis Yamamoto H Wiley-VCH Weinheim 2000
5. Inukai T, Kojima T, J. Org. Chem. 1966 31 1121
6. Biallas M J., Shriver D F., J. Am. Chem. Soc. 1966 88 375
7. Wuest J D., Acc. Chem. Res. 1999 32 81
8. Grdeni D, Korpar- olig B, Sikirica M, Bruvo M, J. Organomet. Chem. 1982 238 327
9. Ooi T, Takahashi M, Maruoka K, J. Am. Chem. Soc. 1996 118 11307
10. Maruoka K, Catal. Today 2001 66 33
11. see ref. 9
12. Li H, Marks T J., Proc. Natl. Acad. Sci. U.S.A. 2006 103 15295
13. For reviews, see:, Taylor M S., Jacobsen E N., Angew. Chem. Int. Ed. 2006 45 1520
14. Connon S J., Chem. Commun. 2008 2499
15. Akiyama T, Itoh J, Fuchibe K, Adv. Synth. Catal. 2006 348 999
16. Takemoto Y, Chem. Pharm. Bull. 2010 58 593
17. Pihko P M., Angew. Chem. Int. Ed. 2004 43 2062
18. Schreiner P R., Chem. Soc. Rev. 2003 32 289
19. Okino T, Hoashi Y, Takemoto Y, J. Am. Chem. Soc. 2003 125 12672
20. Hoashi Y, Okino T, Takemoto Y, Angew. Chem. Int. Ed. 2005 44 4032
21. For reviews, see:, Lee A Y., Stewart J D., Clardy J, Ganem B, Chem. Biol. 1995 2 195
22. Ganem B, Angew. Chem., Int. Ed. Engl. 1996 35 936
23. Kessler S N., Wegner H A., Org. Lett. 2010 12 4062
24. Kessler S N., Neuburger M, Wegner H A., Eur. J. Org. Chem. 2011 3238
25. Drew M G. B., Yates P C., Troch-Grimshaw J, Lavery A, McKillop K P., Nelson S M., Nelson J, J. Chem. Soc., Dalton Trans. 1988 347
26. Drew M G. B., Yates P C., Paul B P., Nelson J, Inorg. Chim. Acta 1986 118 37
27. Xiao N, Xu Q, Sun J, Chen J, Dalton Trans. 2005 3250
28. Austin M, Gebreyes K, Kuivila H G., Swami K, Zubieta J A., Organometallics 1987 6 834
29. Gabbai F P., Schier A, Riede J, Hynes M J., Chem. Commun. 1998 897
30. Isobe K, Okeya S, Meanwell N J., Smith A J., Adams H, Maitlis P M., J. Chem. Soc., Dalton Trans. 1984 1215
31. Rashidi M, Nabavizadeh S M., Zare A, Jamali S, Puddephatt R J., Inorg. Chem. 2010 49 8435
32. Jaska C A., Emslie D J. H., Bosdet M J. D., Piers W E., Sorensen T S., Parvez M, J. Am. Chem. Soc. 2006 128 10885
33. Lorbach A, Bolte M, Lerner H.-W, Wagner M, Chem. Commun. 2010 46 3592
34. Boger D L., Tetrahedron 1983 39 2869
35. Boger D L., Coleman R S., J. Org. Chem. 1984 49 2240
36. Turchi S, Nesi R, Giomi D, Tetrahedron 1998 54 1809
37. Gruseck U, Heuschmann M, Tetrahedron Lett. 1987 28 6027
38. Boger D L., Coleman R S., J. Am. Chem. Soc. 1987 109 2717
39. Bodwell G J., Li J, Angew. Chem. Int. Ed. 2002 41 3261
40. Hartmann K.-P, Heuschmann M, Angew. Chem., Int. Ed. Engl. 1989 28 1267
41. Hartmann K.-P, Heuschmann M, Tetrahedron 2000 56 4213
42. Ernd M, Heuschmann M, Zipse H, Helv. Chim. Acta 2005 88 1491
43. Rooshenas P, Hof K, Schreiner P, Williams C, Eur. J. Org. Chem. 2011 983
44. Bettinger H F., Filthaus M, J. Org. Chem. 2007 72 9750
45. Bader S, Kessler S N., Wegner H A., Synthesis 2010 2759
46. Recently also a protocol accessing 1,2-bis(TMS)- benzene by using Rieke-Mg or Mg turnings in the presence of 1,2-dibromoethane as an entrainer was published:, Lorbach A, Reus C, Bolte M, Lerner H.-W, Wagner M, Adv. Synth. Catal. 2010 352 3443
47. Kaufmann D, Chem. Ber./Recl. 1987 120 901
48. Schacht W, Kaufmann D, J. Organomet. Chem. 1987 331 139
49. Schulz H, Pritzkow H, Siebert W, Chem. Ber. 1991 124 2203
50. Uno H, Okada S, Suzuki H, Tetrahedron 1991 47 6231
51. Sauer J, Heldmann D K., Hetzenegger J, Krauthan J, Sichert H, Schuster J, Eur. J. Org. Chem. 1998 2885