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1
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79955666736
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For reviews, see
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For reviews, see
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3
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2 nd ed. (Eds: A. dea Meijere, F. Diederich), Wiley-VCH, Weinheim, pp.a
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S. Braese, A. de Meijere, in Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed., (Eds: A. dea Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004, pp. 217-315
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(2004)
Metal-Catalyzed Cross-Coupling Reactions
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Braese, S.1
Meijere, A.D.2
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0013319804
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in (Eds.: E. Negishi, A. dea Meijere), Wiley-Interscience, New York, chap.a IV., pp.a
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M. Larhed, A. Hallberg, in Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1 (Eds.:, E. Negishi, A. dea Meijere,), Wiley-Interscience, New York, 2002, chap.a IV. 2, pp. 1133-1178.
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Larhed, M.1
Hallberg, A.2
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5
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84889323392
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The Mizoroki-Heck reaction catalyzed by a metal other than palladium is also known but is rare. For a review, see:, in (Ed.: M. Oestreich), Wiley, Chichester, pp.a
-
The Mizoroki-Heck reaction catalyzed by a metal other than palladium is also known but is rare. For a review, see:, L. Ackermann, R. Born, in Mizoroki-Heck Reaction (Ed.:, M. Oestreich,), Wiley, Chichester, 2009, pp. 383-403.
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(2009)
Mizoroki-Heck Reaction
, pp. 383-403
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Ackermann, L.1
Born, R.2
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6
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79955671333
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For reviews of homolytic aromatic substitution with aryl radicals, see
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For reviews of homolytic aromatic substitution with aryl radicals, see
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8
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78149244809
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Wiley, Chichester, Chaptera , pp.a
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J. Fossey, D. Lefort, J. Sorba, Free Radicals in Organic Chemistry, Wiley, Chichester, 1995, Chaptera 14, pp. 166-180
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Lefort, D.2
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0002523168
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in (Eds.: P. Renaud, M.a P. Sibi), Wiley-VCH, Weinheim, chap.a , pp.a
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A. Studer, M. Bossart, in Radicals in Organic Synthesis, Vol. 2 (Eds.:, P. Renaud, M.a P. Sibi,), Wiley-VCH, Weinheim, 2001, chap.a 1.4, pp. 62-80.
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(2001)
Radicals in Organic Synthesis, Vol. 2
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Studer, A.1
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For a recent review, see
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For a recent review, see:, M. R. Heinrich, Chem. Eur. J. 2009, 15, 820-833.
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Chem. Eur. J.
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Heinrich, M.R.1
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11
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79955650418
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KOtBu in combination with or without a bidentate nitrogen-containing ligand is used in the coupling of aryl halides with (hetero)arenes, where generation of aryl radicals from aryl halides is considered to be involved
-
KOtBu in combination with or without a bidentate nitrogen-containing ligand is used in the coupling of aryl halides with (hetero)arenes, where generation of aryl radicals from aryl halides is considered to be involved
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12
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58449085051
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S. Yanagisawa, K. Ueda, T. Taniguchi, K. Itami, Org. Lett. 2008, 10, 4673-4676
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(2008)
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Ueda, K.2
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78049346852
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W. Liu, H. Cao, H. Zhang, H. Zhang, K. H. Chung, C. He, H. Wang, F. Y. Kwong, A. Lei, J. Am. Chem. Soc. 2010, 132, 16737-16740
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(2010)
J. Am. Chem. Soc.
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Liu, W.1
Cao, H.2
Zhang, H.3
Zhang, H.4
Chung, K.H.5
He, C.6
Wang, H.7
Kwong, F.Y.8
Lei, A.9
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14
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78649513306
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We have reported that coupling of aryl halides with arenes mediated by NaOtBu proceeds through a homolytic aromatic substitution pathway, where a catalytic amount of a phenanthroline derivative is essential for generation of the aryl radical from aryl halides
-
C.-L. Sun, H. Li, D.-G. Yu, M. Yu, X. Zhou, X.-Y. Lu, K. Huang, S.-F. Zheng, B.-J. Li, Z.-J. Shi, Nat. Chem. 2010, 2, 1044-1049. We have reported that coupling of aryl halides with arenes mediated by NaOtBu proceeds through a homolytic aromatic substitution pathway, where a catalytic amount of a phenanthroline derivative is essential for generation of the aryl radical from aryl halides
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(2010)
Nat. Chem.
, vol.2
, pp. 1044-1049
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Sun, C.-L.1
Li, H.2
Yu, D.-G.3
Yu, M.4
Zhou, X.5
Lu, X.-Y.6
Huang, K.7
Zheng, S.-F.8
Li, B.-J.9
Shi, Z.-J.10
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15
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78149233868
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For a discussion on the mechanism of these reactions, see
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E. Shirakawa, K. Itoh, T. Higashino, T. Hayashi, J. Am. Chem. Soc. 2010, 132, 15537-15539. For a discussion on the mechanism of these reactions, see
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Shirakawa, E.1
Itoh, K.2
Higashino, T.3
Hayashi, T.4
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79955664984
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in press; Angew. Chem. Int. Ed. 2011, in press
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A. Studer, D.a P. Curran Angew. Chem. 2011, in press; Angew. Chem. Int. Ed. 2011, in press.
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Angew. Chem.
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Studer, A.1
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17
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0038818627
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The coupling of iodobenzene with styrene in the absence of any transition-metal catalysts is reported to take place at a high temperature and a high pressure in supercritical water, thus giving stilbene in a moderate yield
-
The coupling of iodobenzene with styrene in the absence of any transition-metal catalysts is reported to take place at a high temperature and a high pressure in supercritical water, thus giving stilbene in a moderate yield., R. Zhang, F. Zhao, M. Sato, Y. Ikushima, Chem. Commun. 2003, 1548-1549.
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(2003)
Chem. Commun.
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Zhang, R.1
Zhao, F.2
Sato, M.3
Ikushima, Y.4
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18
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79955659766
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note
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For the reactions shown in Tablea 1-Tablea 3, KOtBu, which was purchased from Wako Pure Chemicals Industries, Ltd. (product number 163-08425), was used as received. Its ICP-AES and ICP-MS analysis showed that the contents of Co, Ni, Ru, Rh, Pd, Ag, Ir, Pt, and Au are less than 0.05a ppm and those of Fe and Cu are 1.0a ppm and 1.1a ppm, respectively. See also Ref.a [8].
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-
-
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19
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79955675037
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note
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The reaction using a sublimed grade KOtBu (99.99 % purity, Aldrich Co., product number 659878) or a KOtBu purified through sublimation by us gave coupling product 3 ao in a similar yield (80 % or 79 % yield, respectively). The contents of Fe and Cu in the sublimed KOtBu are <0.2a ppm (under detection limit) and 0.25a ppm, respectively (ICP-AES analysis). These results amply indicate that the coupling is promoted by KOtBu itself rather than catalyzed by contaminated transition metals. We asked Dr. Kazufumi Kohno to repeat the reaction and he confirmed that the reaction under the same conditions gave 3 ao in 71 % yield.
-
-
-
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20
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79955667111
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note
-
N,N-Dimethylacetamide and dimethylsulfoxide also were effective as solvents but addition of their enolates to styrene and the coupling products took place and thus the yield of 3 ao was slightly lower than that obtained when DMF was used.
-
-
-
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21
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79955652134
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note
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The products are all Ea isomers. The corresponding Za isomer or 1,1-disubstitued product was not observed in any reaction in Tablea 2.
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-
-
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22
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26644442183
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See also Ref.a [3b]
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J. F. Bunnett, Acc. Chem. Res. 1978, 11, 413-420. See also Ref.a [3b].
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Acc. Chem. Res.
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Bunnett, J.F.1
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23
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0001170141
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E. C. Ashby, A. B. Goel, R. N. DePriest, J. Org. Chem. 1981, 46, 2429-2431
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(1981)
J. Org. Chem.
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Depriest, R.N.3
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0009470786
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C. G. Screttas, M. Micha-Screttas, C. T. Cazianis, Tetrahedron Lett. 1983, 24, 3287-3288
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Tetrahedron Lett.
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, pp. 3287-3288
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Cazianis, C.T.3
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48749140575
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E. C. Ashby, D.-H. Bae, W.-S. Park, R. N. Depriest, W.-Y. Su, Tetrahedron Lett. 1984, 25, 5107-5110
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(1984)
Tetrahedron Lett.
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Ashby, E.C.1
Bae, D.-H.2
Park, W.-S.3
Depriest, R.N.4
Su, W.-Y.5
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27
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79955671842
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note
-
A large amount of biphenyls having a tert-butoxy, dimethylamino, or hydroxy group at the 3- or 4-positions, all of which are most likely to be produced through 4-phenylbenzyne, was observed as by-products. These by-products were produced also in the coupling reaction but in lower amounts.
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-
-
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28
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0007819366
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J. W. Sease, F. G. Burton, S. L. Nickol, J. Am. Chem. Soc. 1968, 90, 2595-2598
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J. Grimshaw, Electrochemical Reactions and Mechanisms in Organic Chemistry, Elsevier, Amsterdam, 2000, pp. 54-56, pp. 122-126, and pp. 239-243.
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Grimshaw, J.1
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For examples, see
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V. W. Bowry, J. Lusztyk, K. U. Ingold, J. Am. Chem. Soc. 1991, 113, 5687-5698
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Ogawa, A.1
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Sonoda, N.3
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