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

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

Author keywords

[No Author keywords available]

Indexed keywords

BASE; IODINE DERIVATIVE; SILOXANE;

EID: 0034625934     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001305g     Document Type: Letter
Times cited : (250)

References (32)
  • 17
    • 0034708636 scopus 로고    scopus 로고
    • ref 18, 20 therein
    • 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.
    • (2000) J. Org. Chem. , vol.65 , pp. 1780-1787
    • Nishihara, Y.1    Ikegashira, K.2    Hirabayashi, K.3    Ando, J.4    Mori, A.5    Hiyama, T.6
  • 18
    • 12944337041 scopus 로고    scopus 로고
    • 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.
    • (2000) J. Synth. Org. Chem. , vol.58 , pp. 274
    • Ito, H.1    Hosomi, A.2
  • 19
    • 0034051970 scopus 로고    scopus 로고
    • 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.
    • (2000) Bull. Chem. Soc. Jpn. , vol.73 , pp. 985-990
    • Nishihara, Y.1    Ikegashira, K.2    Toriyama, F.3    Mori, A.4    Hiyama, T.5
  • 20
    • 0032483728 scopus 로고    scopus 로고
    • 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.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 11196-11197
    • Ito, H.1    Ishizuka, T.2    Tateiwa, J.3    Sonoda, M.4    Hosomi, A.5
  • 21
    • 0032558619 scopus 로고    scopus 로고
    • 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.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7893-7896
    • Hirabayashi, K.1    Nishihara, Y.2    Mori, A.3    Hiyama, T.4
  • 22
    • 12944317718 scopus 로고    scopus 로고
    • note
    • Excess TBAF (50% equivalent excess) did not affect the yield.
  • 23
    • 12944256394 scopus 로고    scopus 로고
    • note
    • 2 3 in the N-arylation of arylboronic acid is required. No product was obtained in its absence.
  • 24
    • 12944300881 scopus 로고    scopus 로고
    • note
    • 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
    • 12944293612 scopus 로고    scopus 로고
    • note
    • 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
    • 12944277662 scopus 로고    scopus 로고
    • note
    • 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
    • 12944311501 scopus 로고    scopus 로고
    • note
    • 1a-b
  • 29
    • 12944277661 scopus 로고    scopus 로고
    • note
    • 2 gave no product.
  • 30
    • 0033549829 scopus 로고    scopus 로고
    • 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.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 2413-2416
    • Wolfe, J.P.1    Buchwald, S.L.2
  • 31
    • 0033597748 scopus 로고    scopus 로고
    • 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.
    • (1999) J. Org. Chem. , vol.64 , pp. 5575-5580
    • Hartwig, J.P.1    Kawatsura, M.2    Hauck, S.I.3    Shaughnessy, K.H.4    Alcazar, L.M.5
  • 32
    • 0000290980 scopus 로고    scopus 로고
    • 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).
    • (2000) Org. Lett. , vol.2 , pp. 1233-1236
    • Collman, J.P.1    Zhong, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.