Copper-promoted C-N bond cross-coupling with hypervalent aryl siloxanes and room-temperature N-arylation with aryl iodide [5]

Journal of the American Chemical Society

Volumn 122, Issue 31, 2000, Pages 7600-7601

  Lam, Patrick Y S ^a   Deudon, Sophie ^a   Averill, Kristin M ^a   Li, Renhua ^a   He, Ming Y ^a   DeShong, Philip ^a,b   Clark, Charles G ^a  

^a DUPONT COMPANY   (United States)

^b Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BASE; IODINE DERIVATIVE; SILOXANE;

CHEMICAL BOND; CHEMICAL STRUCTURE; LETTER; REACTION ANALYSIS; TEMPERATURE;

EID: 0034625934     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001305g     Document Type: Letter

References (32)

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10. (c) For solid-phase version of N-arylation see: Combs, A. P.; Saubern, S.; Rafalski, M.; Lam, P. Y. S. Tetrahedron Lett. 1999, 40, 1623-1626.
11. (d) Combs, A. P.; Rafalski, M. J. Combinatorial Chem. 2000, 2, 29-32.
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17. For transmetalation from silicon to copper see: (a) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780-1787 (ref 18, 20 therein). (b) Ito, H.; Hosomi, A. J. Synth. Org. Chem. 2000, 58, 274. (c) Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985-990. (d) Ito, H.; Ishizuka, T.; Tateiwa, J.; Sonoda, M,; Hosomi, A. J. Am. Chem. Soc. 1998, 120, 11196-11197. (e) Hirabayashi, K.; Nishihara, Y.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 7893-7896.
18. For transmetalation from silicon to copper see: (a) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780-1787 (ref 18, 20 therein). (b) Ito, H.; Hosomi, A. J. Synth. Org. Chem. 2000, 58, 274. (c) Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985-990. (d) Ito, H.; Ishizuka, T.; Tateiwa, J.; Sonoda, M,; Hosomi, A. J. Am. Chem. Soc. 1998, 120, 11196-11197. (e) Hirabayashi, K.; Nishihara, Y.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 7893-7896.
19. For transmetalation from silicon to copper see: (a) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780-1787 (ref 18, 20 therein). (b) Ito, H.; Hosomi, A. J. Synth. Org. Chem. 2000, 58, 274. (c) Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985-990. (d) Ito, H.; Ishizuka, T.; Tateiwa, J.; Sonoda, M,; Hosomi, A. J. Am. Chem. Soc. 1998, 120, 11196-11197. (e) Hirabayashi, K.; Nishihara, Y.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 7893-7896.
20. For transmetalation from silicon to copper see: (a) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780-1787 (ref 18, 20 therein). (b) Ito, H.; Hosomi, A. J. Synth. Org. Chem. 2000, 58, 274. (c) Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985-990. (d) Ito, H.; Ishizuka, T.; Tateiwa, J.; Sonoda, M,; Hosomi, A. J. Am. Chem. Soc. 1998, 120, 11196-11197. (e) Hirabayashi, K.; Nishihara, Y.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 7893-7896.
21. For transmetalation from silicon to copper see: (a) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780-1787 (ref 18, 20 therein). (b) Ito, H.; Hosomi, A. J. Synth. Org. Chem. 2000, 58, 274. (c) Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985-990. (d) Ito, H.; Ishizuka, T.; Tateiwa, J.; Sonoda, M,; Hosomi, A. J. Am. Chem. Soc. 1998, 120, 11196-11197. (e) Hirabayashi, K.; Nishihara, Y.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 7893-7896.
22. Excess TBAF (50% equivalent excess) did not affect the yield.
23. 2 3 in the N-arylation of arylboronic acid is required. No product was obtained in its absence.
24. We believe tetra-n-butylammonium fluoride is not the base since in theory all fluoride is consumed stoichiometrically by the formation of Si-F bond with aryl trimethylsiloxane.
25. 5 a more reactive siloxane was used, but the yield remained the same. The use of phenyl triethylsiloxane instead of phenyl trimethylsiloxane also gave similar yields in the case of benzimidazole.
26. On the contrary, benzamide gave only 9% N-arylation after heating at 70 °C. We are currently investigating the significance and utility of this chelating effect of α-heteroatoms on N-arylation. We thank Dr. Elizabeth Hauptman of DuPont CR&D for this observation.
27. 1a-b
28. Murata, M.; Suzuki, K.; Watanabe, S.; Masuda, Y. J. Org. Chem. 1997, 62, 8569-8571.
29. 2 gave no product.
30. In general, N-arylation using Buchwald and Hartwig chemistry requires either elevated temperature or strong base (Nat-BuO). During the course of this work, we became aware that some room-temperature N-arylation of Buchwald/Hartwig chemistry is possible, although still in the presence of stong base Na t-BuO. (a) Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413-2416. (b) Hartwig, J. P.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar, L. M. J. Org. Chem. 1999, 64, 5575-5580.
31. In general, N-arylation using Buchwald and Hartwig chemistry requires either elevated temperature or strong base (Nat-BuO). During the course of this work, we became aware that some room-temperature N-arylation of Buchwald/Hartwig chemistry is possible, although still in the presence of stong base Na t-BuO. (a) Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413-2416. (b) Hartwig, J. P.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar, L. M. J. Org. Chem. 1999, 64, 5575-5580.
32. 2 catalyzes the N-phenylation of benzimidazole with hypervalent phenyl trimethoxysiloxane (69% yield) at 50 °C in DMF (Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236).