Selective synthesis of 1,4-dialkylbenzenes from terephthalic acid

Advanced Synthesis and Catalysis

Volumn 352, Issue 13, 2010, Pages 2195-2199

  Bramborg, Andrea ^a   Linker, Torsten ^a  

^a UNIVERSITY OF POTSDAM   (Germany)

Author keywords

Alkylations; Arenes; Birch reductions; Reaction mechanisms; Synthetic methods

Indexed keywords

EID: 77956894522     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000322     Document Type: Article

References (40)

1. a) The Alkyl Benzenes, (Ed.: F. M. Peter), National Academy Press, Washington, D.C., 1981
2. b) Modern Arene Chemistry, (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2002.
3. Books: a) Friedel-Crafts and Related Reactions, Vol. II, Part I, (Ed. : G. A. Olah), Wiley-Intersience, New York, 1964
4. b) R. M. Roberts, A.A. Khalaf, Friedel-Crafts Alkylation Chemistry: A Century of Discovery, Marcel Dekker, New York, 1984
5. c) Catalytic Asymmetric Friedel-Crafts Alkylations, (Eds.: M. Bandini, A. UmaniRonchi), Wiley-VCH, Weinheim, 2009.
6. J. Jovanovic, F. Boberg, G. R. Schultze, Justus Liebigs Ann. Chem. 1966, 696, 55-63.
7. Books: a) Metal-Catalyzed Cross-Coupling Reactions, (Eds. : A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004
8. b) Modern Arylation Methods, (Ed.: L. Ackermann), Wiley-VCH, Weinheim, 2009
9. c) boron: N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483
10. d) Grignard: C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217-6254
11. e) B.D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500-1531
12. f) zinc: G. Cahiez, L. Foulgoc, A. Moyeux, Angew. Chem. 2009, 121, 3013-3016
13. Angew. Chem. Int. Ed. 2009, 48, 2969-2972
14. g) indium: M. A. Pena, J. Pérez Sestelo, L. A. Sarandeses, Synthesis 2005, 485-492.
15. Industrial Organic Chemistry, (Eds. : K. Weissermel, H.J. Arpe), Wiley-VCH, Weinheim, 2003.
16. Recent examples: a) L. J. Gooßen, C Linder, N. Rodriguez, P. P. Lange, A. Fromm, Chem. Commun. 2009, 7173-7175
17. b) L. J. Gooßen, N. Rodríguez, P. P. Lange, C Linder, Angew. Chem. Int. Ed. 2010, 49, 1111-1114
18. c) reviews: L. J. Gooßen, N. Rodriguez, K. Gooßen, Angew. Chem. 2008, 120, 3144-3164
19. Angew. Chem. Int. Ed. 2008, 47, 3100-3120
20. d) L.J. Gooßen, K. Gooßen, N. Rodriguez, M. Blanchot, C. Linder, B. Zimmermann, Pure Appl. Chem. 2008, 80, 1725-1733.
21. a) T. Linker, K. Vorndran, German Patent DE 19819375.0, 1998
22. b) K. Vorndran, T. Linker, Angew. Chem. 2003, 115, 2593-2595
23. Angew. Chem. Int. Ed. 2003, 42, 2489-2491.
24. T. Krüger, K. Vorndran, T. Linker, Chem. Eur. J. 2009, 15, 12082-12091.
25. Reviews: a)P. W. Rabideau, Tetrahedron 1989, 45, 1579-1603
26. b) P.W. Rabideau, Z. Marcinow, Org. React. 1992, 42, 1-334
27. c) G. S. R. Subba-Rao, Pure Appl. Chem. 2003, 75, 1443-1451.
28. a) H. van Bekkum, C. B. van den Bosch, G. van Minnen-Pathuis, J. C. de Mos, A. M. van Wijk, Reci. Trav. Chim. Pays-Bas 1971, 90, 137-149
29. b) M. Acheson, R. F. Flowerday, J. Chem. Soc. Perkin Trans. 1 1974, 2339-2342
30. c) A. J. Birch, J. Slobbe, Aust. J. Chem. 1977, 30, 1045-1049.
31. a) T. Linker, L. Fröhlich, Angew. Chem. 1994, 106, 2064-2066
32. Angew. Chem. Int. Ed. Engl. 1994, 33, 1971-1972
33. b) T. Linker, L. Fröhlich, J. Am. Chem. Soc. 1995, 117, 2694-2697.
34. R. G. Harvey, L. Arzadon, Tetrahedron 1969, 25, 4887-4894.
35. a) A. J. Baker, A. C. Goudie, J. Chem. Soc. Chem. Commun. 1972, 951
36. b) A. J. Birch, J. Slobbe, Tetrahedron Lett. 1976, 24, 2079-2082
37. c) G. Binmore, J. C. Walton, L. Cardellini, J. Chem. Soc. Chem. Commun. 1995, 27-28.
38. a) R. C Chiechi, G. Sonmez, F. Wudl, Adv. Funct. Mater. 2005, 15, 427-432
39. b) K. T. Nielsen, H. Spanggaard, F. C. Krebs, Macromolecules 2005, 38, 1180-1189
40. c) D. Mössinger, S.-S. Jester, E. Sigmund, U. Müller, S. Höger, Macromolecules 2009, 42, 7974-7978.