A Novel Diarylation Reaction of Alkynes by Using Aryltributylstannane in the Presence of Palladium Catalyst

Some alkynes were diarylated by aryltributylstannane 2 in the presence of palladium salt in moderate to good yield with high stereoselectivity. The reaction was catalytic in palladium using copper(II) chloride dihydrate as a reoxidant.

[1]  G. D. Allred,et al.  Copper-Mediated Cross-Coupling of Organostannanes with Organic Iodides at or below Room Temperature , 1996 .

[2]  E. Piers,et al.  Intermolecular copper(I) chloride-mediated coupling of alkenyltrialkylstannane functions: A convenient synthesis of conjugated diene systems , 1996 .

[3]  J. Falck,et al.  Tin-Copper Transmetalation: Cross-Coupling of .alpha.-Heteroatom-Substituted Alkyltributylstannanes with Organohalides , 1995 .

[4]  S. Murai,et al.  Pd-Catalyzed Coupling Reaction of Acetylenes, Iodotrimethylsilane, and Organozinc Reagents for the Stereoselective Synthesis of Vinylsilanes , 1995 .

[5]  H. Oda,et al.  Synthesis of 5,12-DiHETE derivative by palladium-catalyzed ternary coupling between vinylic halide, a vinylic tin compound, and norbornadiene , 1995 .

[6]  R. L. Beddoes,et al.  A general method for the coupling of vinyl stannanes , 1995 .

[7]  S. Ikeda,et al.  Regio- and Stereoselective Synthesis of 3,6-Dien-1-ynes by Nickel-Catalyzed Coupling Reaction of Allyl Chlorides, 1-Alkynes, and Alkynyltins , 1994 .

[8]  S. Kapadia,et al.  On the Nature of the "Copper Effect" in the Stille Cross-Coupling , 1994 .

[9]  S. Ikeda,et al.  Synthesis of Stereodefined Enynes by the Nickel-Catalyzed Coupling Reaction of Alkynyltins, Alkynes, and Enones , 1994 .

[10]  J. Falck,et al.  Stereospecific palladium/copper cocatalyzed cross-coupling of .alpha.-alkoxy- and .alpha.-aminostannanes with acyl chlorides , 1994 .

[11]  H. Oda,et al.  Synthesis of cis-olefins via palladium-catalyzed coupling of organic halides, norbornadiene, and organotin compounds , 1993 .

[12]  J. Mague,et al.  Stable bis(silyl)palladium complexes: synthesis, structure, and bis-silylation of acetylenes , 1992 .

[13]  B. Tang,et al.  Synthesis and properties of organometallic rings and macrocycles containing ferrocene, silicon, and unsaturated hydrocarbon units: x-ray crystal structures of the novel ferrocenophanes Fe(.eta.-C5H4)2(SiMe2)2(CH:CH) and trans,trans-Fe(.eta.-C5H4)2(SiMe2)2(CH2CH:CHCH2)2 , 1992 .

[14]  S. Murai,et al.  A new catalytic reaction involving oxidative addition of iodotrimethylsilane (Me3SiI) to palladium(0). Synthesis of stereodefined enynes by the coupling of Me3SiI, acetylenes, and acetylenic tin reagents , 1991 .

[15]  M. Suginome,et al.  Palladium(II) acetate-tert-alkyl isocyanide as a highly efficient catalyst for the inter- and intramolecular bis-silylation of carbon-carbon triple bonds , 1991 .

[16]  T. Hiyama,et al.  Double silylation of 1,4-bis(trimethylsilyl)butadiyne with disilanes using a palladium catalyst. , 1990 .

[17]  L. S. Liebeskind,et al.  3-Stannylcyclobutenediones as nucleophilic cyclobutenedione equivalents. Synthesis of substituted cyclobutenediones and cyclobutenedione monoacetals and the beneficial effect of catalytic copper iodide on the Stille reaction , 1990 .

[18]  H. Sano,et al.  Palladium-catalyzed reaction of organic haldids with organotin compounds involving olefin insertion: synthesis of 2,3-di-substituted norbornanes , 1989 .

[19]  S. Ghosal,et al.  Formation of 1,3-diynes, 1,3-dienes, and biphenyls via the copper(II) nitrate mediated coupling of organotin compounds , 1987 .

[20]  T. Hiyama,et al.  Palladium catalyzed double silylation of bis(trimethylsilyl)butadiyne by means of disilanes , 1987 .

[21]  J. Escudié,et al.  The chemistry of octamethyl-1,2-disilacyclobutane. Some SiSi cleavage and insertion reactions , 1984 .

[22]  R. West,et al.  RING-INSERTION AND RING-OPENING REACTIONS OF OCTAETHYLCYCLOTETRASILANE , 1983 .

[23]  H. Rivière,et al.  Comportement des organomagnesiens vis-a-vis de composes acetyleniques disubstitues en presence de PdCl2 , 1982 .

[24]  M. Michman,et al.  Alkylation reactions with organometallic reagents , 1976 .

[25]  Toshi-aki Kobayashi,et al.  Chemistry of organosilicon compounds , 1976 .

[26]  K. Tamao,et al.  Reaction of bis(substituted-silyl)bipyridylnickel(II) with acetylenes , 1974 .

[27]  M. Michman,et al.  Alkylation reactions with organometallic compounds : II. The reaction of diphenylacetylene with palladium compounds of the type L2PdCl2 and CH3MgBr , 1971 .

[28]  J. Light,et al.  Methyl-transition metal systems and diphenylacetylene , 1970 .