Palladium catalysed cross-coupling of aryl bromides with functionalised arylboronic acids in the presence of a tetraphosphine ligand

Synlett

Volumn , Issue 11, 2002, Pages 1807-1810

  Feuerstein, Marie ^a   Berthiol, Florian ^a   Doucet, Henri ^a   Santelli, Maurice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Aryl bromides; Arylboronic acids; Catalysis; Palladium; Tetraphosphine

Indexed keywords

BORONIC ACID DERIVATIVE; BROMINE DERIVATIVE; CYCLOPENTANE DERIVATIVE; LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0036420063     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34896     Document Type: Article

References (32)

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4. For reviews on the cross-coupling of aryl halides with arylboronic acids: (a) Suzuki, A. J. Organomet. Chem. 2002, 653, 83. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (c) Suzuki, A. Metal-Catalysed Cross-Coupling Reaction; Diederich, F.; Stang, P. J., Eds.; Wiley: New York, 1998. (d) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium Catalysed Organic Reactions; Academic Press: San Diego, 1997. (e) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
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6. For reviews on the cross-coupling of aryl halides with arylboronic acids: (a) Suzuki, A. J. Organomet. Chem. 2002, 653, 83. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (c) Suzuki, A. Metal-Catalysed Cross-Coupling Reaction; Diederich, F.; Stang, P. J., Eds.; Wiley: New York, 1998. (d) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium Catalysed Organic Reactions; Academic Press: San Diego, 1997. (e) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
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8. For recent examples of efficient catalysts for Suzuki cross-coupling: (a) Beller, M.; Fischer, H.; Herrmann, A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (c) Weissman, H.; Milstein, D. Chem. Commun. 1999, 1901. (d) Wolfe, J.; Buchwald, S. Angew. Chem., Int. Ed. 1999, 38, 2413. (e) Zapf, A.; Beller, M. Chem.-Eur. J. 2000, 6, 1830. (f) Mc Guiness, D.; Cavell, K. Organometallics 2000, 19, 741. (g) Bedford, R.; Welch, S. Chem. Commun. 2001, 129.
9. For recent examples of efficient catalysts for Suzuki cross-coupling: (a) Beller, M.; Fischer, H.; Herrmann, A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (c) Weissman, H.; Milstein, D. Chem. Commun. 1999, 1901. (d) Wolfe, J.; Buchwald, S. Angew. Chem., Int. Ed. 1999, 38, 2413. (e) Zapf, A.; Beller, M. Chem.-Eur. J. 2000, 6, 1830. (f) Mc Guiness, D.; Cavell, K. Organometallics 2000, 19, 741. (g) Bedford, R.; Welch, S. Chem. Commun. 2001, 129.
10. For recent examples of efficient catalysts for Suzuki cross-coupling: (a) Beller, M.; Fischer, H.; Herrmann, A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (c) Weissman, H.; Milstein, D. Chem. Commun. 1999, 1901. (d) Wolfe, J.; Buchwald, S. Angew. Chem., Int. Ed. 1999, 38, 2413. (e) Zapf, A.; Beller, M. Chem.-Eur. J. 2000, 6, 1830. (f) Mc Guiness, D.; Cavell, K. Organometallics 2000, 19, 741. (g) Bedford, R.; Welch, S. Chem. Commun. 2001, 129.
11. For recent examples of efficient catalysts for Suzuki cross-coupling: (a) Beller, M.; Fischer, H.; Herrmann, A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (c) Weissman, H.; Milstein, D. Chem. Commun. 1999, 1901. (d) Wolfe, J.; Buchwald, S. Angew. Chem., Int. Ed. 1999, 38, 2413. (e) Zapf, A.; Beller, M. Chem.-Eur. J. 2000, 6, 1830. (f) Mc Guiness, D.; Cavell, K. Organometallics 2000, 19, 741. (g) Bedford, R.; Welch, S. Chem. Commun. 2001, 129.
12. For recent examples of efficient catalysts for Suzuki cross-coupling: (a) Beller, M.; Fischer, H.; Herrmann, A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (c) Weissman, H.; Milstein, D. Chem. Commun. 1999, 1901. (d) Wolfe, J.; Buchwald, S. Angew. Chem., Int. Ed. 1999, 38, 2413. (e) Zapf, A.; Beller, M. Chem.-Eur. J. 2000, 6, 1830. (f) Mc Guiness, D.; Cavell, K. Organometallics 2000, 19, 741. (g) Bedford, R.; Welch, S. Chem. Commun. 2001, 129.
13. For recent examples of efficient catalysts for Suzuki cross-coupling: (a) Beller, M.; Fischer, H.; Herrmann, A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (c) Weissman, H.; Milstein, D. Chem. Commun. 1999, 1901. (d) Wolfe, J.; Buchwald, S. Angew. Chem., Int. Ed. 1999, 38, 2413. (e) Zapf, A.; Beller, M. Chem.-Eur. J. 2000, 6, 1830. (f) Mc Guiness, D.; Cavell, K. Organometallics 2000, 19, 741. (g) Bedford, R.; Welch, S. Chem. Commun. 2001, 129.
14. For recent examples of efficient catalysts for Suzuki cross-coupling: (a) Beller, M.; Fischer, H.; Herrmann, A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (c) Weissman, H.; Milstein, D. Chem. Commun. 1999, 1901. (d) Wolfe, J.; Buchwald, S. Angew. Chem., Int. Ed. 1999, 38, 2413. (e) Zapf, A.; Beller, M. Chem.-Eur. J. 2000, 6, 1830. (f) Mc Guiness, D.; Cavell, K. Organometallics 2000, 19, 741. (g) Bedford, R.; Welch, S. Chem. Commun. 2001, 129.
15. For recent examples of Suzuki cross-coupling with functionalised arylboronic acids: (a) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170. (b) Old, D.; Wolfe, J.; Buchwald, S. J. Am. Chem. Soc. 1998, 120, 9722. (c) Wolfe, J.; Singer, R.; Yang, B.; Buchwald, S. J. Am. Chem. Soc. 1999, 121, 9550. (d) Blettner, C.; Konig, W.; Stenzel, W.; Schotten,T. J. Org. Chem. 1999, 64, 3885. (e) Zhang, C.; Huang, J.; Trudell, M.; Nolan, S. J. Org. Chem. 1999, 64, 3804. (f) Zhang, T.; Allen, M. Tetrahedron Lett. 1999, 40, 5813. (g) Littke, A.; Dai, C.; Fu, G. J. Am. Chem. Soc. 2000, 122, 4020. (h) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (i) Grasa, G.; Hillier, A.; Nolan, S. Org. Lett. 2001, 3, 1077.
16. For recent examples of Suzuki cross-coupling with functionalised arylboronic acids: (a) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170. (b) Old, D.; Wolfe, J.; Buchwald, S. J. Am. Chem. Soc. 1998, 120, 9722. (c) Wolfe, J.; Singer, R.; Yang, B.; Buchwald, S. J. Am. Chem. Soc. 1999, 121, 9550. (d) Blettner, C.; Konig, W.; Stenzel, W.; Schotten,T. J. Org. Chem. 1999, 64, 3885. (e) Zhang, C.; Huang, J.; Trudell, M.; Nolan, S. J. Org. Chem. 1999, 64, 3804. (f) Zhang, T.; Allen, M. Tetrahedron Lett. 1999, 40, 5813. (g) Littke, A.; Dai, C.; Fu, G. J. Am. Chem. Soc. 2000, 122, 4020. (h) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (i) Grasa, G.; Hillier, A.; Nolan, S. Org. Lett. 2001, 3, 1077.
17. For recent examples of Suzuki cross-coupling with functionalised arylboronic acids: (a) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170. (b) Old, D.; Wolfe, J.; Buchwald, S. J. Am. Chem. Soc. 1998, 120, 9722. (c) Wolfe, J.; Singer, R.; Yang, B.; Buchwald, S. J. Am. Chem. Soc. 1999, 121, 9550. (d) Blettner, C.; Konig, W.; Stenzel, W.; Schotten,T. J. Org. Chem. 1999, 64, 3885. (e) Zhang, C.; Huang, J.; Trudell, M.; Nolan, S. J. Org. Chem. 1999, 64, 3804. (f) Zhang, T.; Allen, M. Tetrahedron Lett. 1999, 40, 5813. (g) Littke, A.; Dai, C.; Fu, G. J. Am. Chem. Soc. 2000, 122, 4020. (h) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (i) Grasa, G.; Hillier, A.; Nolan, S. Org. Lett. 2001, 3, 1077.
18. For recent examples of Suzuki cross-coupling with functionalised arylboronic acids: (a) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170. (b) Old, D.; Wolfe, J.; Buchwald, S. J. Am. Chem. Soc. 1998, 120, 9722. (c) Wolfe, J.; Singer, R.; Yang, B.; Buchwald, S. J. Am. Chem. Soc. 1999, 121, 9550. (d) Blettner, C.; Konig, W.; Stenzel, W.; Schotten, T. J. Org. Chem. 1999, 64, 3885. (e) Zhang, C.; Huang, J.; Trudell, M.; Nolan, S. J. Org. Chem. 1999, 64, 3804. (f) Zhang, T.; Allen, M. Tetrahedron Lett. 1999, 40, 5813. (g) Littke, A.; Dai, C.; Fu, G. J. Am. Chem. Soc. 2000, 122, 4020. (h) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (i) Grasa, G.; Hillier, A.; Nolan, S. Org. Lett. 2001, 3, 1077.
19. For recent examples of Suzuki cross-coupling with functionalised arylboronic acids: (a) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170. (b) Old, D.; Wolfe, J.; Buchwald, S. J. Am. Chem. Soc. 1998, 120, 9722. (c) Wolfe, J.; Singer, R.; Yang, B.; Buchwald, S. J. Am. Chem. Soc. 1999, 121, 9550. (d) Blettner, C.; Konig, W.; Stenzel, W.; Schotten, T. J. Org. Chem. 1999, 64, 3885. (e) Zhang, C.; Huang, J.; Trudell, M.; Nolan, S. J. Org. Chem. 1999, 64, 3804. (f) Zhang, T.; Allen, M. Tetrahedron Lett. 1999, 40, 5813. (g) Littke, A.; Dai, C.; Fu, G. J. Am. Chem. Soc. 2000, 122, 4020. (h) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (i) Grasa, G.; Hillier, A.; Nolan, S. Org. Lett. 2001, 3, 1077.
20. For recent examples of Suzuki cross-coupling with functionalised arylboronic acids: (a) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170. (b) Old, D.; Wolfe, J.; Buchwald, S. J. Am. Chem. Soc. 1998, 120, 9722. (c) Wolfe, J.; Singer, R.; Yang, B.; Buchwald, S. J. Am. Chem. Soc. 1999, 121, 9550. (d) Blettner, C.; Konig, W.; Stenzel, W.; Schotten, T. J. Org. Chem. 1999, 64, 3885. (e) Zhang, C.; Huang, J.; Trudell, M.; Nolan, S. J. Org. Chem. 1999, 64, 3804. (f) Zhang, T.; Allen, M. Tetrahedron Lett. 1999, 40, 5813. (g) Littke, A.; Dai, C.; Fu, G. J. Am. Chem. Soc. 2000, 122, 4020. (h) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (i) Grasa, G.; Hillier, A.; Nolan, S. Org. Lett. 2001, 3, 1077.
21. For recent examples of Suzuki cross-coupling with functionalised arylboronic acids: (a) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170. (b) Old, D.; Wolfe, J.; Buchwald, S. J. Am. Chem. Soc. 1998, 120, 9722. (c) Wolfe, J.; Singer, R.; Yang, B.; Buchwald, S. J. Am. Chem. Soc. 1999, 121, 9550. (d) Blettner, C.; Konig, W.; Stenzel, W.; Schotten, T. J. Org. Chem. 1999, 64, 3885. (e) Zhang, C.; Huang, J.; Trudell, M.; Nolan, S. J. Org. Chem. 1999, 64, 3804. (f) Zhang, T.; Allen, M. Tetrahedron Lett. 1999, 40, 5813. (g) Littke, A.; Dai, C.; Fu, G. J. Am. Chem. Soc. 2000, 122, 4020. (h) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (i) Grasa, G.; Hillier, A.; Nolan, S. Org. Lett. 2001, 3, 1077.
22. For recent examples of Suzuki cross-coupling with functionalised arylboronic acids: (a) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170. (b) Old, D.; Wolfe, J.; Buchwald, S. J. Am. Chem. Soc. 1998, 120, 9722. (c) Wolfe, J.; Singer, R.; Yang, B.; Buchwald, S. J. Am. Chem. Soc. 1999, 121, 9550. (d) Blettner, C.; Konig, W.; Stenzel, W.; Schotten, T. J. Org. Chem. 1999, 64, 3885. (e) Zhang, C.; Huang, J.; Trudell, M.; Nolan, S. J. Org. Chem. 1999, 64, 3804. (f) Zhang, T.; Allen, M. Tetrahedron Lett. 1999, 40, 5813. (g) Littke, A.; Dai, C.; Fu, G. J. Am. Chem. Soc. 2000, 122, 4020. (h) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (i) Grasa, G.; Hillier, A.; Nolan, S. Org. Lett. 2001, 3, 1077.
23. For recent examples of Suzuki cross-coupling with functionalised arylboronic acids: (a) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170. (b) Old, D.; Wolfe, J.; Buchwald, S. J. Am. Chem. Soc. 1998, 120, 9722. (c) Wolfe, J.; Singer, R.; Yang, B.; Buchwald, S. J. Am. Chem. Soc. 1999, 121, 9550. (d) Blettner, C.; Konig, W.; Stenzel, W.; Schotten, T. J. Org. Chem. 1999, 64, 3885. (e) Zhang, C.; Huang, J.; Trudell, M.; Nolan, S. J. Org. Chem. 1999, 64, 3804. (f) Zhang, T.; Allen, M. Tetrahedron Lett. 1999, 40, 5813. (g) Littke, A.; Dai, C.; Fu, G. J. Am. Chem. Soc. 2000, 122, 4020. (h) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (i) Grasa, G.; Hillier, A.; Nolan, S. Org. Lett. 2001, 3, 1077.
24. For a review on the synthesis of polypodal diphenylphosphine ligands, see: Laurenti, D.; Santelli, M. Org. Prep. Proced. Int. 1999, 31, 245.
25. (a) Laurenti, D.; Feuerstein, M.; Pèpe, G.; Doucet, H.; Santelli, M. J. Org. Chem. 2001, 66, 1633.
26. (b) Feuerstein, M.; Laurenti, D.; Doucet, H.; Santelli, M. Chem. Commun. 2001, 43.
27. (a) Feuerstein, M.; Laurenti, D.; Bougeant, C.; Doucet, H.; Santelli, M. Chem. Commun. 2001, 325.
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32. 3): δ = 8.00 (d, J = 8.5 Hz, 2 H), 7.64 (d, J = 8.5 Hz, 2 H), 7.56 (d, J = 8.7 Hz, 2 H), 6.99 (d, J = 8.7 Hz, 2 H), 3.85 (s, 3 H), 2.62 (s, 3 H).