Ni(0)-Trialkylphosphine Complexes. Efficient Homo-coupling Catalyst for Aryl, Alkenyl, and Heteroaromatic Halides

Bis(trialkylphosphine)nickel(0) generated in situ from bis(trialkylphosphine)nickel(II) chloride was found to be an effective catalyst for a homo-coupling of aryl, alkenyl, or heteroaromatic halides with zinc powder. The catalytic reaction proceeded very well in NMP or HMPA solvent under mild conditions to afford dehalogenative-coupling products in good yields.

[1]  J. Labadie,et al.  Mechanisms of the palladium-catalyzed couplings of acid chlorides with organotin reagents , 1983 .

[2]  R. Rieke,et al.  Activated metallic nickel as a reagent for the dehalogenative coupling of halobenzenes , 1983 .

[3]  R. Rieke,et al.  Metallic nickel as a reagent for the coupling of aromatic and benzylic halides , 1983 .

[4]  P. Helquist,et al.  Reaction of aryl and vinyl halides with zerovalent nickel - preparative aspects and the synthesis of alnusone , 1982 .

[5]  K. Takagi,et al.  The in Situ-generated Nickel(0)-catalyzed Reaction of Aryl Halides with Potassium Iodide and Zinc Powder , 1980 .

[6]  J. Stille,et al.  Mechanisms of 1,1-reductive elimination from palladium , 1980 .

[7]  K. Klabunde,et al.  .pi.-Arene complexes of nickel(II). Synthesis (from metal atoms) of (.pi.-arene)bis(pentafluorophenyl)nickel(II). Properties, .pi.-arene lability, and chemistry , 1980 .

[8]  Y. Ban,et al.  Preparation and synthetic use of the zerovalent nickel complex by electrochemical reduction , 1980 .

[9]  J. Kochi,et al.  Nickel catalysis in halogen exchange with aryl and vinylic halides , 1980 .

[10]  J. Kochi,et al.  Mechanism of biaryl synthesis with nickel complexes , 1979 .

[11]  J. Stille,et al.  Mechanisms of oxidative addition of organic halides to Group 8 transition-metal complexes , 1977 .

[12]  R. Rieke,et al.  Highly reactive transition metal powders. Oxidative insertion of nickel, palladium, and platinum metal powders into aryl-halide bonds , 1977 .

[13]  J. Mahan,et al.  Oxidative additions of aryl, vinyl, and acyl halides to triethylphosphinenickel(0) complexes , 1977 .

[14]  G. W. Parshall SIGMA‐ARYL COMPOUNDS OF NICKEL, PALLADIUM, AND PLATINUM, SYNTHESIS AND BONDING STUDIES , 1974 .

[15]  C. A. Tolman,et al.  Triarylphosphine and ethylene complexes of zerovalent nickel, palladium, and platinum , 1972 .

[16]  P. Helquist,et al.  Synthesis with Zerovalent Nickel. Coupling of Alkenyl Halides with Bis(1,5-cyclooctadiene)nickel(0) , 1971 .

[17]  C. Wilkins,et al.  The Mechanism of the Prins Reaction. V. The Prins Reaction of Styrenes1 , 1966 .

[18]  P. C. Kvande,et al.  Stereochemistry of 5-Co-ordinated Compounds. III. Some New Phosphine Complexes of Divalent Nickel and Cobalt. , 1963 .

[19]  H. Wynberg,et al.  Studies in the Synthesis of Long-chain Compounds1,2 , 1956 .

[20]  C. D. Hurd,et al.  THE USE OF GRIGNARD REAGENTS IN ATTEMPTED SYNTHESES OF ASYMMETRIC ALLENE BASES , 1927 .

[21]  T. Zincke Zur Kenntniss der Ditolyle , 1871 .