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Related catalytic aryl-aryl coupling via C-H bond cleavage. Rh: (a) Oi, S.; Fukita, S.; Inoue. Y. Chem. Commun. 1998, 2439. (b) Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem., Int. Ed. 2003, 42, 112. Ru: (c) Oi, S.; Fukita, S.; Hitrata, N.; Wakatsuki, N.; Miyano, S.; Inoue, Y. Org. Lett. 2001, 3, 2579. (d) Oi. S.; Ogino, Y.; Fukita, S.; Inoue, Y. Org. Lett. 2002, 4, 1783. (e) Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698.
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2-sp bonds is known. The reaction is generally considered to involve in situ generation of terminal alkynes, while it would proceed partly via β-carbon elimination. (a) Huynh, C.; Linstrumelle, G. Tetrahedron 1988, 44, 6337. (b) Chow, H.-F.; Wan, C.-W.; Low, K.-H.; Y. Yeung, Y.-Y. J. Org. Chem. 2001, 66, 1910. (c) Choi, C.-K.; Tomita, I.; Endo, T. Chem. Lett. 1999, 1253.
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2-sp bonds is known. The reaction is generally considered to involve in situ generation of terminal alkynes, while it would proceed partly via β-carbon elimination. (a) Huynh, C.; Linstrumelle, G. Tetrahedron 1988, 44, 6337. (b) Chow, H.-F.; Wan, C.-W.; Low, K.-H.; Y. Yeung, Y.-Y. J. Org. Chem. 2001, 66, 1910. (c) Choi, C.-K.; Tomita, I.; Endo, T. Chem. Lett. 1999, 1253.
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0033474575
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2-sp bonds is known. The reaction is generally considered to involve in situ generation of terminal alkynes, while it would proceed partly via β-carbon elimination. (a) Huynh, C.; Linstrumelle, G. Tetrahedron 1988, 44, 6337. (b) Chow, H.-F.; Wan, C.-W.; Low, K.-H.; Y. Yeung, Y.-Y. J. Org. Chem. 2001, 66, 1910. (c) Choi, C.-K.; Tomita, I.; Endo, T. Chem. Lett. 1999, 1253.
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Del Río, D.6
Carmona, E.7
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42
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0038367561
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note
-
3 for 24 h, however, gave 6 with a lower yield of 13% together with 4 (22%) and 5 (60%), which may be due to catalyst deactivation. Precipitation of Pd black was observed after the reaction.
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43
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0031585711
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(a) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441.
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45
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0038029411
-
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note
-
1H NMR spectra were obtained in the case of compounds 8-11. Their methyl peaks also coalesced by heating with the exception of those of 9.
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-
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46
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0000770954
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The formation of palladacycle D from A may involve electrophilic attack of the palladium on the ε-carbon followed by elimination of an arene, although participation of another path via a Pd(IV) species cannot be excluded. See: (a) Dyker, G. Chem. Ber. Recl. 1997, 130, 1567. (b) Catellani, M. Synlett 2003, 298. The formation of 2-substituted naphthalenes with higher yields than those expected suggests participation of another reduction mechanism. However, the details are unclear.
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Dyker, G.1
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47
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0037288964
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The formation of palladacycle D from A may involve electrophilic attack of the palladium on the ε-carbon followed by elimination of an arene, although participation of another path via a Pd(IV) species cannot be excluded. See: (a) Dyker, G. Chem. Ber. Recl. 1997, 130, 1567. (b) Catellani, M. Synlett 2003, 298. The formation of 2-substituted naphthalenes with higher yields than those expected suggests participation of another reduction mechanism. However, the details are unclear.
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Synlett
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Catellani, M.1
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48
-
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0038029410
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note
-
The fact that the total yield of 3a and 4 is somewhat greater than 100% may be due to the participation of homocoupling of 1a to some extent. However, formation of homocoupling products was not observed or was negligible (less than 2%) in the other reactions.
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49
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0033603837
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Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527.
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Goodson, F.E.1
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Rh: Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 9307.
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(b) Grushin, V. V.; Alper, H. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, Germany, 1999; p 193.
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0037112673
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Review for the recent development of Pd-catalyzed arylation reactions with aryl chlorides including aryl-aryl coupling with use of arylmetals: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
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0001873339
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Ojima, I., Ed.; John Wiley Sons: New York
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Catalytic asymmetric aryl-aryl coupling: For review: (a) Ogasawara, M.; Hayashi, T. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; John Wiley Sons: New York, 2000; p 651.
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Ogasawara, M.1
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0000213981
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Asymmetric Kumada-Tamao coupling to give the same binaphthyl with up to 37% ee: Frejd, T.; Klingstedt, T. Acta Chem. Scand. 1989, 43, 670.
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Frejd, T.1
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0038367563
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note
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3, however, did not proceed. The reason is not definitive at the present stage.
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