1,8-bis(diphenylmethylium)naphthalenediyl dication as an organic oxidant: synthesis of benzidines via self-coupling of N,N-dialkylanilines.

doi:10.1002/CHIN.200513098

Paper

1,8-bis(diphenylmethylium)naphthalenediyl dication as an organic oxidant: synthesis of benzidines via self-coupling of N,N-dialkylanilines.

Published Nov 2, 2004 · Terunobu Saitoh, S. Yoshida, J. Ichikawa

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22

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2

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Abstract

1,8-Bis(diphenylmethylium)naphthalenediyl dications promoted oxidative coupling of various N,N-dialkylanilines to afford the corresponding para-coupled bisanilines, benzidines, in good to excellent yield. The dications were readily prepared from a cyclic ether precursor, derived from 1,8-dibromonaphthalene, via deoxygenation with a silylating reagent in 1,1,1,3,3,3-hexafluoro-2-propanol under anhydrous conditions. [reaction: see text]

Study Snapshot

1,8-bis(diphenylmethylium)naphthalenediyl dications effectively promote oxidative coupling of N,N-dialkylanilines, leading to benzidines in good to excellent yield.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

1,8-bis(diphenylmethylium)naphthalenediyl dication as an organic oxidant: synthesis of benzidines via self-coupling of N,N-dialkylanilines.

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References

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Citations

Catalytic and Aerobic Oxidative Biaryl Coupling of Anilines Using a Recyclable Heterogeneous Catalyst for Synthesis of Benzidines and Bicarbazoles.

This study presents a simple, practical, and environmentally friendly method for synthesis of diversely functionalized benzidines and diaminobiphenyls using a recyclable Rh/C catalyst.

9,10-Dihydrophenanthrene with Two Spiro(dibenzocycloheptatriene) Units: A Highly Strained Caged Hydrocarbon Exhibiting Reversible Electrochromic Behavior

Dispiro hydrocarbon 1 exhibits reversible electrochromic behavior, exhibiting drastic color changes and C-C bond formation/cleavage, making it a promising material for applications in electronics and photovoltaics.

Recent advances in direct dehydrogenative biphenyl couplings

Recent advances in dehydrogenative biphenyl couplings enable efficient and direct preparation of biologically important compounds, with potential applications in organic synthesis.

Direct oxidative cyanation of tertiary amines promoted by in situ generated hypervalent iodine(III)-CN intermediate

This study developed an environmentally friendly, metal-free cyanation method for tertiary amines using hypervalent iodine(III)-CN intermediate, yielding up to 74% with various substituent groups.

Extension studies on iron(III)-promoted free radical oxidation of anilines: self-coupling and self-bridged assembling reactions

Iron(III)-promoted free radical oxidation of anilines can easily convert them into self-coupling benzidines and self-bridged assembling diaminodiarylmethanes.