Ambient Temperature, Ullmann-like Reductive Coupling of Aryl, Heteroaryl, and Alkenyl Halides

Zhang, Shijie; Zhang, Dawei; Liebeskind, Lanny S.

doi:10.1021/jo9700078

Cited by 280 publications

(163 citation statements)

References 17 publications

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“…[6] 1,10-phenanthroline and its derivatives, [7] ethylene glycol, [8a] diethylsalicylamide, [8b] amino acids, [9] oximetype and Schiff base ligands, [10] thiophene-2-carboxylate, [11] bidentate phosphines, [12] diphosphinidenecyclobutene, [13] diphenyl pyrrolidine-2-phosphonate [14] and pyrrolidine-2-phosphonic acid phenyl monoester. [15] In this paper, we report a commercially available and efficient bidentate ligand, pipecolinic acid, for the copper-catalyzed N-arylation of nitrogen-containg compounds including a variety of amines, amides, indole and imidazole.…”

Section: Introductionmentioning

confidence: 99%

An Inexpensive and Efficient Copper Catalyst for N‐Arylation of Amines, Amides and Nitrogen‐Containing Heterocycles

et al. 2006

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Section: Introductionmentioning

confidence: 99%

An Inexpensive and Efficient Copper Catalyst for N‐Arylation of Amines, Amides and Nitrogen‐Containing Heterocycles

et al. 2006

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“…85 was then tested in a copper(I)-thiophene-2-carboxylate (CuTC) mediated intramolecular coupling reaction, a reagent which allows coupling reactions to be performed under ambient temperatures. [34] However, this approach proved unsuccessful. Conversion of dialdehyde 85 to the corresponding bis-imine 86 and repeating the CuTCmediated coupling followed by acidic workup afforded the desired biaryl 87 in almost quantitative yield and with a high d.e.…”

Section: Scheme 14mentioning

confidence: 99%

The Application of Molecular Tethers in Controlling Axial Chirality

O`Sullivan¹

2016

MROC

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Type of publicationArticle (peer-reviewed) Abstract: Atropisomeric biaryl compounds are an attractive target in organic chemistry due to their abundance in nature and their utility as ligands in catalysis. Among the methods available for their synthesis, the use of chiral tethers offers very high levels of stereocontrol. In this article, we review the application of molecular tethers in controlling axial chirality across a range of different ligands and natural products.

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“…The organic phase was separated, washed with water (100 mL × 2) and brine solution (100 mL), dried over anhydrous sodium sulphate, filtered and the solvent was removed in vacuum. The product was purified with column chromatography using ethyl acetate-hexane as eluent to obtain brown solid which was recrystallized from hexane [7]. …”

Section: M799 (Page 2)mentioning

confidence: 99%

3,3'-(1,4-Phenylenebis(phenylazanediyl))bis(7-ethoxy-4-methyl-2H-chromen-2-one)

Narayanan

Haridas

2013

Molbank

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3,3'-(1,4-Phenylenebis(phenylazanediyl))bis(7-ethoxy-4-methyl-2H-chromen-2-one) was synthesized from N,N'-diphenylbenzene-1,4-diamine and bromo-7-ethoxy-4-methylcoumarin based on Ullmann coupling reaction. The synthesized compound was characterized by UV-Visible, NMR, FT-IR, MS, elemental analysis and Fluorescence Spectrum.Keywords: coumarin; phenylenediamine; Ullmann coupling reaction; hole transporting material The title compound 3,3'-(1,4-phenylenebis(phenylazanediyl))bis(7-ethoxy-4-methyl-2H-chromen-2-one) is used as an efficient hole and electron transporting materials in optoelectronic devices. Coumarin and its derivatives occur widely in nature, and have been extensively exploited in biological, chemical and physical fields [1]. Coumarins have outstanding optical properties, including an extended spectral range, high quantum yields, superior photostability and good solubility in common solvents. Many natural and synthetic coumarin derivatives are widely used as electroluminescent (EL) materials [2]. Coumarin derivatives have attracted much interest owing to their potential applications in organic light-emitting diodes (OLEDs) [3]. The arylamine moiety fulfills the requirement of easy and reversible oxidation and therefore constitutes the building block of many of the hole-transporting materials [4].N,N'-diphenylbenzene-1,4-diamine was synthesized from p-phenylenediamine and bromobenzene by known procedure [5]. A yellow solid with melting point 135 °C was obtained. 3-bromo-7-ethoxy-4-methyl coumarin was synthesized from 3-bromo-7-hydroxy-4-methylcoumarin and ethyl bromide [6]. A brown solid was obtained which has a melting point of 72 °C. N,N'-diphenylbenzene-1,4-diamine OPEN ACCESS

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Ambient Temperature, Ullmann-like Reductive Coupling of Aryl, Heteroaryl, and Alkenyl Halides

Cited by 280 publications

References 17 publications

An Inexpensive and Efficient Copper Catalyst for N‐Arylation of Amines, Amides and Nitrogen‐Containing Heterocycles

An Inexpensive and Efficient Copper Catalyst for N‐Arylation of Amines, Amides and Nitrogen‐Containing Heterocycles

The Application of Molecular Tethers in Controlling Axial Chirality

3,3'-(1,4-Phenylenebis(phenylazanediyl))bis(7-ethoxy-4-methyl-2H-chromen-2-one)

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