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(a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
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Wolfe, J.P.1
Wagaw, S.2
Marcoux, J.-F.3
Buchwald, S.L.4
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0031585072
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(c) Arnauld, T.; Barton, D. H. R.; Doris, E. Tetrahedron 1997, 53, 4137-4144.
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Tetrahedron
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Arnauld, T.1
Barton, D.H.R.2
Doris, E.3
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5
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33751154516
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(e) Lopez-Alvarado, P.; Avendano, C.; Menendez, J. C. J. Org. Chem. 1995, 60, 5678-5682.
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Lopez-Alvarado, P.1
Avendano, C.2
Menendez, J.C.3
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6
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0032492942
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(a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936.
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Tetrahedron Lett.
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Chan, D.M.T.1
Monaco, K.L.2
Wang, R.-P.3
Winters, M.P.4
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7
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0032492980
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(b) For an improved version of the related O-arylation see also: Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940.
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(1998)
Tetrahedron Lett.
, vol.39
, pp. 2937-2940
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Evans, D.A.1
Katz, J.L.2
West, T.R.3
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8
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0342947550
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(a) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2937-2940.
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Tetrahedron Lett.
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Lam, P.Y.S.1
Clark, C.G.2
Saubern, S.3
Adams, J.4
Winters, M.P.5
Chan, D.M.T.6
Combs, A.7
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9
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0034115347
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(b) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Averill, K.; Chan, D. M. T.; Combs, A. P. Synlett 2000, 674-676.
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Synlett
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Lam, P.Y.S.1
Clark, C.G.2
Saubern, S.3
Adams, J.4
Averill, K.5
Chan, D.M.T.6
Combs, A.P.7
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10
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0033605298
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(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.
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(1999)
Tetrahedron Lett.
, vol.40
, pp. 1623-1626
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Combs, A.P.1
Saubern, S.2
Rafalski, M.3
Lam, P.Y.S.4
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17
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0034708636
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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.
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(2000)
J. Org. Chem.
, vol.65
, pp. 1780-1787
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Nishihara, Y.1
Ikegashira, K.2
Hirabayashi, K.3
Ando, J.4
Mori, A.5
Hiyama, T.6
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18
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12944337041
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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.
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(2000)
J. Synth. Org. Chem.
, vol.58
, pp. 274
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Ito, H.1
Hosomi, A.2
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19
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0034051970
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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.
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(2000)
Bull. Chem. Soc. Jpn.
, vol.73
, pp. 985-990
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Nishihara, Y.1
Ikegashira, K.2
Toriyama, F.3
Mori, A.4
Hiyama, T.5
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20
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0032483728
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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.
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(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 11196-11197
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Ito, H.1
Ishizuka, T.2
Tateiwa, J.3
Sonoda, M.4
Hosomi, A.5
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21
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0032558619
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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.
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(1998)
Tetrahedron Lett.
, vol.39
, pp. 7893-7896
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Hirabayashi, K.1
Nishihara, Y.2
Mori, A.3
Hiyama, T.4
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22
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12944317718
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note
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Excess TBAF (50% equivalent excess) did not affect the yield.
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23
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12944256394
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note
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2 3 in the N-arylation of arylboronic acid is required. No product was obtained in its absence.
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-
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24
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12944300881
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note
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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.
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-
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25
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12944293612
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note
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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.
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-
-
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26
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12944277662
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note
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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.
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27
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12944311501
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note
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1a-b
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28
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1542682245
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Murata, M.; Suzuki, K.; Watanabe, S.; Masuda, Y. J. Org. Chem. 1997, 62, 8569-8571.
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(1997)
J. Org. Chem.
, vol.62
, pp. 8569-8571
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Murata, M.1
Suzuki, K.2
Watanabe, S.3
Masuda, Y.4
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29
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12944277661
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note
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2 gave no product.
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-
-
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30
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0033549829
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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.
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(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 2413-2416
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Wolfe, J.P.1
Buchwald, S.L.2
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31
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0033597748
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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.
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(1999)
J. Org. Chem.
, vol.64
, pp. 5575-5580
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Hartwig, J.P.1
Kawatsura, M.2
Hauck, S.I.3
Shaughnessy, K.H.4
Alcazar, L.M.5
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32
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0000290980
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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).
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(2000)
Org. Lett.
, vol.2
, pp. 1233-1236
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Collman, J.P.1
Zhong, M.2
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