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4
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0003995267
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E. Negishi Wiley-Interscience New York
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The palladium-catalyzed coupling of aryl and alkenyl halides with alkynylmetals is an effective alternative. For a recent review, see: E. Negishi, and C. Xu E. Negishi Handbook of Organopalladium Chemistry for Organic Synthesis 2002 Wiley-Interscience New York 531 549 See also Ref. 1c
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12144289000
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For recent examples, see: (a) J.-M. Altenburger, G.Y. Lassalle, M. Matrougui, D. Galtier, J.-C. Jetha, Z. Bocskei, C.N. Berry, C. Lunven, J. Lorrain, J.-P. Herault, P. Schaeffer, S.E. O'Connor, and J.-M. Herbert Bioorg. Med. Chem. 12 2004 1713 1730
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12
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W.-M. Dai, K.W. Lai, A. Wu, W. Hamaguchi, M.Y.H. Lee, L. Zhou, A. Ishii, and S. Nishimoto J. Med. Chem. 45 2002 758 761
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J.-P. Tranchier, R. Chavignon, D. Prim, A. Auffrant, J.G. Planas, F. Rose-Munch, E. Rose, and G.R. Stephenson Tetrahedron Lett. 42 2001 3311 3313
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24344464696
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Heck and co-workers had already reported the coupling reaction in piperidine at 100°C but they did not mention its efficiency. See Ref. 6.
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Heck and co-workers had already reported the coupling reaction in piperidine at 100°C but they did not mention its efficiency. See Ref. 6.
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23
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For example, see: (a) A. Mori, J. Kawashima, T. Shimada, M. Suguro, K. Hirabayashi, and Y. Nishihara Org. Lett. 2 2000 2935 2937
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For example, see: (a) T. Fukuyama, M. Shinmen, S. Nishitani, M. Sato, and I. Ryu Org. Lett. 4 2002 1691 1694
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It is mentioned that amines sometimes make the work-up procedure troublesome. A. Mori, M.S.M. Ahmed, A. Sekiguchi, K. Masui, and T. Koike Chem. Lett. 2002 756 757 and references cited therein
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15444371592
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2O as a solvent, unfortunately the scope is narrow, where only electron-deficient aryl iodides coupled with phenylacetylene or 3-butyn-1-ol in acceptable yields. G. Zhang Synlett 2005 619 622
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Zhang, G.1
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24344510665
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note
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3, is used effectively in combination with a special media (Ref. 12b) or a special ligand (Refs. 13i and 13l).
-
-
-
-
58
-
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24344499601
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-
note
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To the best of our knowledge, potassium phosphate, one of the most popular bases for the Suzuki-Miyaura coupling reaction, has hardly been used in the Sonogashira coupling and the copper-free version of the reaction.
-
-
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59
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0035944139
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To the best of our knowledge, use of DMSO as a solvent in the palladium-catalyzed coupling reaction of terminal alkynes has only one precedent, where the reaction of an alkyne with a 2-aryl-1,1-dibromoethene gave a diyne by the Sonogashira coupling reaction accompanied by dehydrobromination. H.B. Lee, D.H. Huh, J.S. Oh, G.-H. Min, B.H. Kim, D.H. Lee, J.K. Hwang, and Y.G. Kim Tetrahedron 57 2001 8283 8290
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60
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24344479416
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note
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3 in an aromatic solvent such as toluene and benzene.
-
-
-
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61
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0030903044
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IP as well as other iminophosphine ligands are reported to be a excellent ligand in the following palladium-catalyzed coupling reaction of organostannanes. Cross-coupling reaction with aryl halides: (a) E. Shirakawa, H. Yoshida, and H. Takaya Tetrahedron Lett. 38 1997 3759 3762
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10044289300
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67
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24344489687
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Available from Aldrich Chemical Co.
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Available from Aldrich Chemical Co.
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68
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24344477991
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note
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4 at the beginning and 1.2 equiv after 24 h.
-
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69
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84988204469
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One-pot procedures with the aid of a copper catalyst have already been developed. (a) A. Carpita, A. Lessi, and R. Rossi Synthesis 1984 571 572
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For an example of the trimethylsilylacetylene version of the one-pot method for preparation of symmetrical and unsymmetrical diarylacetylenes, see: M.J. Mio, L.C. Kopel, J.B. Braun, T.L. Gadzikwa, K.L. Hull, R.G. Brisbois, C.J. Markworth, and P.A. Grieco Org. Lett. 4 2002 3199 3202
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73
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0028329356
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In the palladium-catalyzed coupling reaction of aryl halides, aryl groups of triarylphosphine ligands instead of that of the aryl halides sometimes undergo the coupling with nucleophiles through exchange of substituents between palladium and phosphorous atoms. For example, see: (a) G.T. Crisp, and P.T. Glink Tetrahedron 50 1994 3213 3234
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