Phosphides and arsenides as metal–halogen exchange reagents. Part 2. Reactions with aromatic dihalides

Gillespie, Donal G.; Walker, Brian; Stevens, David King; McAuliffe, Charles A.

doi:10.1039/p19830001697

Cited by 17 publications

(5 citation statements)

References 5 publications

(12 reference statements)

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“…(2-Chlorophenyl)diphenylarsine (5). Compound 5 was obtained according to the general procedure. Product 5 was isolated from the reaction mixture by silica gel column chromatography (petroleum ether) to give 5 as a white solid, mp 86−87 °C, yielding 88% of the isolated product.…”

Section: Methodsmentioning

confidence: 99%

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Highly Efficient Palladium-Catalyzed Arsination. Synthesis of a Biphenyl Arsine Ligand and Its Application to Obtain Perfluoroalkylarsines

2009

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An efficient one-pot, two-step Pd-catalyzed arsination with n-Bu3SnAsPh2 (1) and sterically hindered aryl iodides (ArI) with different functional groups is reported. The cross-coupling reactions of this stannane with ArI afforded the functionalized triarylarsines in very good isolated yields (71−88%). By using this methodology, a biphenyl arsine ligand, AsPh2(bph), was achieved, and its use as ligand in the Pd-catalyzed arsination with RfI to obtain perfluoroalkylarsines is also reported. In this reaction, the activity of a variety of phosphine and arsine ligands was investigated. The new biphenyl arsine ligand AsPh2(bph) proved to be the best one for the arsination reaction with RfI.

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Section: Methodsmentioning

confidence: 99%

“…Biphenyl-2-yldiphenylarsine ( 7 ). Compound 7 was obtained according to the general procedure. Product 7 was isolated from the reaction mixture by silica gel column chromatography (petroleum ether).…”

Section: Methodsmentioning

confidence: 99%

Highly Efficient Palladium-Catalyzed Arsination. Synthesis of a Biphenyl Arsine Ligand and Its Application to Obtain Perfluoroalkylarsines

2009

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“…2-(Diphenylphosphinyl)naphthalene: mp = 184−185 °C; 1 H NMR (250 MHz, CDCl 3 ) δ 8.30 (d, J PH = 14 Hz, 1H), 7.88 (d, J = 8.5 Hz, 2H), 7.72−7.68 (m, 4H) , 7.65−7.44 (m, 10H); 31 P NMR (CDCl 3 ) δ 29.19; m / e (CI, NH 3 ) 329 (M + 1).…”

Section: Methodsmentioning

confidence: 99%

Nickel- and Palladium-Catalyzed Homocoupling of Aryl Triflates. Scope, Limitation, and Mechanistic Aspects

1997

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Whereas the direct reduction of aryl triflates affords mainly phenols and some arenes, the presence of a catalytic amount of palladium or nickel results in the formation of biaryls. The homocoupling is performed in the presence of an electron source, either a cathode or zinc powder. A judicious choice of the metal (nickel or palladium), the ligand (monodentate or bidentate phosphine), and the reduction process (electrochemical or chemical) allows the synthesis of functional symmetrical biaryls. Nickel and palladium complexes ligated by bidentate ligands such as NiCl(2)(dppf) and Pd(OAc)(2) + 1 BINAP are very efficient for the homocoupling of 1-naphthyl triflate, since the dimer was obtained in almost quantitative yield. However, the homocoupling is sensitive to steric hindrance, excluding for the moment the synthesis of atropisomers. The homocoupling proceeds via an activation of the C-O bond of the aryl triflate by a palladium(0) (or a nickel(0)) complex, providing an intermediate arylpalladium(II) (or nickel(II)) complex that after activation by electron transfer affords a new complex able to undergo a second oxidative addition with the aryl triflates.

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“…The title compound was prepared following a modified literature method . 1,2-Dibromo-4,5-di- n- butoxybenzene 8 (28.5 g, 75 mmol) and 27.3 mL of freshly distilled furan (25.5 g, 375 mmol) were dissolved in THF (75 mL), freshly distilled from LiAlH 4 .…”

Section: Methodsmentioning

confidence: 99%

“…The title compound was prepared following a modified literature method. 51 1,2-Dibromo-4,5-di-n-butoxybenzene 8 (28.5 g, 75 mmol) and 27.3 mL of freshly distilled furan (25.5 g, 375 mmol) were dissolved in THF (75 mL), freshly distilled from LiAlH 4 . The solution was cooled to −50 °C under Ar, and 46.8 mL (75 mmol) of 1.6 M n-BuLi solution in hexane was added dropwise over a period of 30 min.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Tetraaryltetraanthra[2,3]porphyrins: Synthesis, Structure, and Optical Properties

et al. 2012

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A synthetic route to symmetrical tetraaryltetraanthra[2,3]porphyrins (Ar(4)TAPs) was developed. Ar(4)TAPs bearing various substituents in meso-phenyls and anthracene residues were prepared from the corresponding pyrrolic precursors. The synthesized porphyrins possess high solubility and exhibit remarkably strong absorption bands in the near-infrared region (790-950 nm). The scope of the method, selection of the peripheral substituents, choice of the metal, and their influence on the optical properties are discussed together with the first X-ray crystallographic data for anthraporphyrin.

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Phosphides and arsenides as metal–halogen exchange reagents. Part 2. Reactions with aromatic dihalides

Cited by 17 publications

References 5 publications

Highly Efficient Palladium-Catalyzed Arsination. Synthesis of a Biphenyl Arsine Ligand and Its Application to Obtain Perfluoroalkylarsines

Highly Efficient Palladium-Catalyzed Arsination. Synthesis of a Biphenyl Arsine Ligand and Its Application to Obtain Perfluoroalkylarsines

Nickel- and Palladium-Catalyzed Homocoupling of Aryl Triflates. Scope, Limitation, and Mechanistic Aspects

Tetraaryltetraanthra[2,3]porphyrins: Synthesis, Structure, and Optical Properties

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