Efficient synthesis of well-defined, high molecular weight, and processible polyanilines under mild conditions via palladium-catalyzed amination [8]

Journal of the American Chemical Society

Volumn 122, Issue 31, 2000, Pages 7606-7607

  Zhang, Xiao Xiang ^a   Sadighi, Joseph P ^a   Mackewitz, Thomas W ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; CATALYSIS; CATALYST; CHEMICAL BOND; LETTER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION;

EID: 0034625890     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001718h     Document Type: Letter

References (27)

1. For reviews on polyaniline, see: (a) MacDiarmid, A. G.; Epstein, A. J. Faraday Discuss. Chem. Soc. 1989, 88, 317. (b) Heeger, A. J. Synth. Met. 1993, 55-57, 3471. (c) MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1995, 69, 85. (d) MacDiarmid, A. G. Synth. Met. 1997, 84, 27.
2. For reviews on polyaniline, see: (a) MacDiarmid, A. G.; Epstein, A. J. Faraday Discuss. Chem. Soc. 1989, 88, 317. (b) Heeger, A. J. Synth. Met. 1993, 55-57, 3471. (c) MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1995, 69, 85. (d) MacDiarmid, A. G. Synth. Met. 1997, 84, 27.
3. For reviews on polyaniline, see: (a) MacDiarmid, A. G.; Epstein, A. J. Faraday Discuss. Chem. Soc. 1989, 88, 317. (b) Heeger, A. J. Synth. Met. 1993, 55-57, 3471. (c) MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1995, 69, 85. (d) MacDiarmid, A. G. Synth. Met. 1997, 84, 27.
4. For reviews on polyaniline, see: (a) MacDiarmid, A. G.; Epstein, A. J. Faraday Discuss. Chem. Soc. 1989, 88, 317. (b) Heeger, A. J. Synth. Met. 1993, 55-57, 3471. (c) MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1995, 69, 85. (d) MacDiarmid, A. G. Synth. Met. 1997, 84, 27.
5. (a) MacDiarmid, A. G.; Chiang, J. C.; Richter, A. F.; Somasiri, N. L. D.; Epstein, A. J. In Conducting Polymers; Alcacer, L., Ed.; Reifel: Dordrecht, The Netherlands, 1987; pp 105-120.
6. (b) Gospodinova, N.; Terlemezyan, L. Prog. Polym. Sci. 1998, 23, 1443.
7. Angelopoulos, M.; Asturias, G. E.; Ermer, S. P.; Ray, A.; Scherr, E. M.; MacDiarmid, A. G.; Akhtar, M.; Kiss, Z.; Epstein, A. J. Mol. Cryst. Liq. Cryst. 1988, 160, 151.
8. (a) Cao, Y.; Smith, P.; Heeger, A. J. Synth. Met. 1992, 48, 91.
9. (b) Xia, Y.; Wiesinger, J. M.; MacDiarmid, A. G.; Epstein, A. J. Chem. Mater. 1995, 7, 443.
10. (a) Adams, P. N.; Monkman, A. P. Synth. Met. 1997, 87, 165.
11. (b) Beadle, P. M.; Nicolau, Y. F.; Banka, E.; Rannou, P.; Djurado, D. Synth. Met. 1998, 95, 29.
12. Wudl, F.; Angus, R. O.; Lu, F. L.; Allemand, P. M.; Vachon, D. J.; Nowak, M.; Liu, Z. X.; Heeger, A. J. J. Am. Chem. Soc. 1987, 109, 3677.
13. Wei, L.; Kumar, J.; Tripathy, S.; Senecal, K. J.; Samuelson, L. J. Am. Chem. Soc. 1999, 121, 71.
14. For reviews on palladium-catalyzed amination, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (b) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046. (c) Yang, B. Y.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
15. For reviews on palladium-catalyzed amination, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (b) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046. (c) Yang, B. Y.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
16. For reviews on palladium-catalyzed amination, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (b) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046. (c) Yang, B. Y.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
17. (a) Harwood: E. A.; Sigurdsson, S. T.; Edfeldt, N. B. F.; Reid, B. R.; Hopkins, P. B. J. Am. Chem. Soc. 1999, 121, 5081.
18. (b) Liang, L.-C.; Schrock, R. R.; Davis, W. M.; McConville, D. H. J. Am. Chem. Soc. 1999, 121, 5797.
19. (c) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251.
20. Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527 and references therein.
21. (a) Singer, R. A.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 213.
22. (b) Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 4960.
23. (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
24. (b) Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 2413.
25. (c) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
26. Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441.
27. Various MW values of polyanilines prepared by aniline oxidation were reported in the literature. They were typically determined in NMP using emeraldine base form with addition of LiCl at elevated column temperature. Many factors can influence the MW determinations. See ref 5 and references therein for detailed discussions.