Novel oxidative coupling of 2-naphthols to 1,1′-bi-2-naphthols catalysed by solid Lewis acids using atmospheric oxygen as oxidant

Li, Tong‐Shuang; Duan, Hui-Yun; Li, Baozhi; Tewari, Brij Bhushan; Li, Shenghui

doi:10.1039/a808656g

Cited by 28 publications

(12 citation statements)

References 19 publications

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“…68 In this case, a two-component molecular crystal containing both compounds in a 1 : 1 ratio (93) 69 Typically, the substrate and 0.2 eq. of the supported iron salt were heated in xylene at reflux for 20 min whilst air was bubbled through the mixture.…”

Section: Naphtholsmentioning

confidence: 99%

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Iron(iii) chloride in oxidative C–C coupling reactions

2009

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In this critical review, the use of iron(III) chloride in oxidative C-C couplings of arenes and related unsaturated compounds is presented and reviewed. The approach allows highly selective dimerisations of phenol derivatives, naphthols, and heterocyclic compounds. Sequential couplings give access to structurally well-defined oligo- and polymers. Iron(III) chloride is commercially available and inexpensive. Being a mild oxidising agent it has been applied in numerous reactions leading to new carbon-carbon-bonds in complex molecular arrays (107 references).

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Section: Naphtholsmentioning

confidence: 99%

“…or silica gel give solid Lewis acids, which have been applied by Li et al in the catalytic oxidative couplings of 84a and 84b. 69 Typically, the substrate and 0.2 eq. of the supported iron salt were heated in xylene at reflux for 20 min whilst air was bubbled through the mixture.…”

Section: Naphtholsmentioning

confidence: 99%

Iron(iii) chloride in oxidative C–C coupling reactions

2009

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“…Li and co-workers have used a series of solid Lewis acids, including FeCl 3 /Al 2 O 3 and FeCl 3 /SiO 2 , for the oxidative coupling of 2-naphthols 22 to 1,1'-bi-2-naphthols 23, in excellent yields (Scheme 12) [39]. The authors have utilised the same conditions for oxidative coupling of naphthalene-2-thiols yielding the corresponding bi (2naphthol) disulfides in high yields without detectable formation of 1,1'-binaphthalene-2,2'-dithiol.…”

Section: Oxidative Couplingsmentioning

confidence: 99%

Recent Uses of Iron (III) Chloride in Organic Synthesis

Díaz¹,

Miranda²,

Padrón³

et al. 2006

COC

125

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Iron (III) chloride is extensively used in organic synthesis as an ideal Lewis acid since it is an inexpensive, efficient, stable, environmentally friendly and a convenient agent for several useful reactions such as; polymerisations, oxidations, oxidative couplings, reductions, C C bond formation, Ferrier rearrangement, one-pot multicomponent condensations, Friedel-Crafts reactions, cyclisations, glycosidation, Prins-type cyclisation, deprotection of various functional groups, and as a reagent in key steps of natural products synthesis. This comprehensive review attempts to cover the advances in this field, which have occurred in the last five years.

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“…Iron(III) chloride has also been dispersed onto alumina and montmorillonite to perform the same kind of reaction [104,105]. In a study of these reagents, Li and co-workers showed that similar yields could be obtained in very short reaction times (Table 33).…”

Section: Reagents Supported On Inorganic Materialsmentioning

confidence: 99%

Oxidative Aryl‐Coupling Reactions in Synthesis

Lessène

Feldman

2002

Modern Arene Chemistry

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The oxidant-mediated coupling of electron-rich arene rings has served over several decades as a valuable procedure to access biaryl units. The complex mixtures of isomers that often plagued the earliest studies have gradually given way to synthetically useful product distributions upon application of more selective coupling protocols. Continual advances in the nature of the oxidant (and its attendant ligands) and more precisely defined reaction conditions have led to increasing levels of control upon CaC bond formation. Chemoselective (CaC vs. CaO bond formation with phenols; suppression of product oxidation), regioselective (o-o 0 , vs. o-p 0 vs. p-p 0 CaC bond formation), and, more recently, stereoselective (atropisomer-selective) biaryl bond formation can now be achieved in many well-defined systems. A survey of the more recent advances in these areas is presented.14.1

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Novel oxidative coupling of 2-naphthols to 1,1′-bi-2-naphthols catalysed by solid Lewis acids using atmospheric oxygen as oxidant

Cited by 28 publications

References 19 publications

Iron(iii) chloride in oxidative C–C coupling reactions

Iron(iii) chloride in oxidative C–C coupling reactions

Recent Uses of Iron (III) Chloride in Organic Synthesis

Oxidative Aryl‐Coupling Reactions in Synthesis

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