-
1
-
-
20544450502
-
-
For general reviews of metal-catalyzed cross-coupling reactions, see: a, Eds, A. de Meijere, F. Diederich, Wiley-VCH, Weinheim
-
For general reviews of metal-catalyzed cross-coupling reactions, see: a) Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004;
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions
-
-
-
4
-
-
53549116071
-
-
Aldrich, Milwaukee
-
b) A. Suzuki, H. C. Brown, Organic Synthesis via Boranes, Vol. 3, Aldrich, Milwaukee, 2003;
-
(2003)
Organic Synthesis via Boranes
, vol.3
-
-
Suzuki, A.1
Brown, H.C.2
-
6
-
-
0032747809
-
-
For examples, see: a
-
For examples, see: a) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550;
-
(1999)
J. Am. Chem. Soc
, vol.121
, pp. 9550
-
-
Wolfe, J.P.1
Singer, R.A.2
Yang, B.H.3
Buchwald, S.L.4
-
7
-
-
0034600318
-
-
b) A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020;
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 4020
-
-
Littke, A.F.1
Dai, C.2
Fu, G.C.3
-
8
-
-
0037047555
-
-
c) N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553.
-
(2002)
J. Org. Chem
, vol.67
, pp. 5553
-
-
Kataoka, N.1
Shelby, Q.2
Stambuli, J.P.3
Hartwig, J.F.4
-
11
-
-
12344251733
-
-
For general reviews, see: a
-
For general reviews, see: a) M. R. Netherton, G. C. Fu, Adv. Synth. Catal. 2004, 346, 1525;
-
(2004)
Adv. Synth. Catal
, vol.346
, pp. 1525
-
-
Netherton, M.R.1
Fu, G.C.2
-
14
-
-
34547789922
-
-
For an additional leading reference, see
-
For an additional leading reference, see: B. Saito, G. C. Fu, J. Am. Chem. Soc. 2007, 129, 9602.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 9602
-
-
Saito, B.1
Fu, G.C.2
-
15
-
-
34249104674
-
-
a) A. Roglans, A. Pla-Quintana, M. Moreno-Mañas, Chem. Rev. 2006, 106, 4622;
-
(2006)
Chem. Rev
, vol.106
, pp. 4622
-
-
Roglans, A.1
Pla-Quintana, A.2
Moreno-Mañas, M.3
-
17
-
-
1342332888
-
-
c) T. Saeki, E.-C. Son, K. Tamao, Org. Lett. 2004, 6, 617;
-
(2004)
Org. Lett
, vol.6
, pp. 617
-
-
Saeki, T.1
Son, E.-C.2
Tamao, K.3
-
19
-
-
33846667022
-
-
e) L. K. Hwang, Y. Na, J. Lee, Y. Do, S. Chang, Angew. Chem. 2005, 117, 6322;
-
(2005)
Angew. Chem
, vol.117
, pp. 6322
-
-
Hwang, L.K.1
Na, Y.2
Lee, J.3
Do, Y.4
Chang, S.5
-
21
-
-
1542377701
-
-
a) F. Kakiuchi, M. Usui, S. Ueno, N. Chatani, S. Murai, J. Am. Chem. Soc. 2004, 126, 2706;
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 2706
-
-
Kakiuchi, F.1
Usui, M.2
Ueno, S.3
Chatani, N.4
Murai, S.5
-
22
-
-
33845946746
-
-
b) S. Ueno, E. Mizushima, N. Chatani, F. Kakiuchi, J. Am. Chem. Soc. 2006, 128, 16516.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 16516
-
-
Ueno, S.1
Mizushima, E.2
Chatani, N.3
Kakiuchi, F.4
-
23
-
-
0000532523
-
-
a) E. Wenkert, E. L. Michelotti, C. S. Swindell, J. Am. Chem. Soc. 1979, 101, 2246;
-
(1979)
J. Am. Chem. Soc
, vol.101
, pp. 2246
-
-
Wenkert, E.1
Michelotti, E.L.2
Swindell, C.S.3
-
24
-
-
0001626633
-
-
b) E. Wenkert, E. L. Michelotti, C. S. Swindell, M. Tingoli, J. Org. Chem. 1984, 49, 4894;
-
(1984)
J. Org. Chem
, vol.49
, pp. 4894
-
-
Wenkert, E.1
Michelotti, E.L.2
Swindell, C.S.3
Tingoli, M.4
-
27
-
-
53549118762
-
-
Notes: a) The amount of PCy3 was not optimized for each substrate. In the reaction of p-acetylanisole (see Table 2, entry 6, the use of 20 mol% of PCy3 gave a inferior result (30% yield, Thus, we routinely conducted the reaction with 40 mol% of PCy3; b) When the corresponding pinacolate was used for the reaction in Table 2, entry 1, the yield of the product was decreased 20% yield
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3; b) When the corresponding pinacolate was used for the reaction in Table 2, entry 1, the yield of the product was decreased (20% yield).
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Oxidative addition of aryl methyl ethers in this catalysis may involve an intermediate in which the aromaticity of the aryl methyl ether is lost, such as η2-arene or Meisenheimer-type complexes. Polyaromatic compounds are expected to form such complexes more facilely, since part of the aromaticity is retained after complex formation
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2-arene or Meisenheimer-type complexes. Polyaromatic compounds are expected to form such complexes more facilely, since part of the aromaticity is retained after complex formation.
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-
-
-
29
-
-
84985723178
-
-
a) W. Kaschube, K. R. Pörschke, K. Angermund, C. Krüger, G. Wilke, Chem. Ber. 1988, 121, 1921;
-
(1988)
Chem. Ber
, vol.121
, pp. 1921
-
-
Kaschube, W.1
Pörschke, K.R.2
Angermund, K.3
Krüger, C.4
Wilke, G.5
-
30
-
-
0037073838
-
-
b) F. Mongin, L. Mojovic, B. Guillamet, F. Trécourt, G. Quéguiner, J. Org. Chem. 2002, 67, 8991;
-
(2002)
J. Org. Chem
, vol.67
, pp. 8991
-
-
Mongin, F.1
Mojovic, L.2
Guillamet, B.3
Trécourt, F.4
Quéguiner, G.5
-
32
-
-
29844439845
-
-
Another possible explanation for the wider substrate scope in the cross-couplings with Grignard reagents is activation of C-O bonds by Lewis acidic magnesiumsalts. However, the addition of MgBr2, LiCl, and BPh3 in our system did not improve the reactivity of aryl methyl ethers. See: a N. Yoshikai, H. Mashima, E. Nakamura, J. Am. Chem. Soc. 2005, 127, 17978;
-
3 in our system did not improve the reactivity of aryl methyl ethers. See: a) N. Yoshikai, H. Mashima, E. Nakamura, J. Am. Chem. Soc. 2005, 127, 17978;
-
-
-
-
33
-
-
33847633018
-
-
b) Y. Nakao, A. Yada, S. Ebata, T. Hiyama, J. Am. Chem. Soc. 2007, 129, 2428.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 2428
-
-
Nakao, Y.1
Yada, A.2
Ebata, S.3
Hiyama, T.4
-
34
-
-
0003085584
-
-
For leading examples, see: a
-
For leading examples, see: a) Y. Kiso, K. Tamao, M. Kumada, J. Organomet. Chem. 1973, 50, C12;
-
(1973)
J. Organomet. Chem
, vol.50
-
-
Kiso, Y.1
Tamao, K.2
Kumada, M.3
-
35
-
-
0001432809
-
-
b) V. P. W. Böhm, C. W. K. Gstöttmayr, T. Weskamp, W. A. Herrmann, Angew. Chem. 2001, 113, 3500;
-
(2001)
Angew. Chem
, vol.113
, pp. 3500
-
-
Böhm, V.P.W.1
Gstöttmayr, C.W.K.2
Weskamp, T.3
Herrmann, W.A.4
-
39
-
-
33644539961
-
-
e) L. Ackermann, R. Born, J. H. Spatz, D. Meyer, Angew. Chem. 2005, 117, 7382;
-
(2005)
Angew. Chem
, vol.117
, pp. 7382
-
-
Ackermann, L.1
Born, R.2
Spatz, J.H.3
Meyer, D.4
-
40
-
-
27844437252
-
-
Angew. Chem. Int. Ed. 2005, 44, 7216. See also references [12b] and [13a].
-
Angew. Chem. Int. Ed. 2005, 44, 7216. See also references [12b] and [13a].
-
-
-
-
41
-
-
38149100971
-
-
For a review, see
-
For a review, see: M. Tobisu, N. Chatani, Chem. Soc. Rev. 2008, 37, 300.
-
(2008)
Chem. Soc. Rev
, vol.37
, pp. 300
-
-
Tobisu, M.1
Chatani, N.2
-
43
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40549128684
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During preparation of this manuscript, another report on Kumada-type coupling of aryl methyl ethers with methylmagnesium halides was published: B.-T. Guan, S.-K. Xiang, T. Wu, Z.-P. Sun, B.-Q. Wang, K.-Q. Zhao, Z.-J. Shi, Chem. Commun. 2008, 1437.
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During preparation of this manuscript, another report on Kumada-type coupling of aryl methyl ethers with methylmagnesium halides was published: B.-T. Guan, S.-K. Xiang, T. Wu, Z.-P. Sun, B.-Q. Wang, K.-Q. Zhao, Z.-J. Shi, Chem. Commun. 2008, 1437.
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See also
-
See also: B.-T. Guan, S.-K. Xiang, B.-Q. Wang, Z.-P. Sun, Y. Wang, K.-Q. Zhao, Z.-J. Shi, J. Am. Chem. Soc. 2008, 130, 3268.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 3268
-
-
Guan, B.-T.1
Xiang, S.-K.2
Wang, B.-Q.3
Sun, Z.-P.4
Wang, Y.5
Zhao, K.-Q.6
Shi, Z.-J.7
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45
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A cross-coupling reaction between activated aryl fluorides and boronic acids has been reported: T. Schaub, M. Backes, U. Radius, J. Am. Chem. Soc. 2006, 128, 15964.
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A cross-coupling reaction between activated aryl fluorides and boronic acids has been reported: T. Schaub, M. Backes, U. Radius, J. Am. Chem. Soc. 2006, 128, 15964.
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