A Concise Synthetic Approach
Towards Hydroxytetraphenylenes

Jian-Fang Cui; Hui Huang; Henry N. C. Wong

doi:10.1055/s-0030-1259708

LETTER

A Concise Synthetic Approach Towards Hydroxytetraphenylenes

Jian-Fang Cui^a, Hui Huang^a, Henry N. C. Wong*^a,b
^a Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
^b Department of Chemistry, Center of Novel Functional Molecules, and Institute of Molecular Functional Materials,1 The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. of China
Fax: +85226035057; e-Mail: hncwong@cuhk.edu.hk;

Abstract

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Abstract

This communication is concerned with our efforts in improving the syntheses of five hydroxytetraphenylens, which we obtained before. A short consecutive direct ortho-metalation and oxidative coupling sequence from N-pivaloyl-protected substituted aniline provided the corresponding 2,2′-diiodobiphenyls. Subsequently, copper(II)-mediated oxidative coupling of 2,2′-diiodobiphenyls successfully led to the formation of the corresponding hydroxytetraphenylenes. This is the first time that hydroxytetraphenylenes 2, 4 and 5 were all realized via oxidative cross-coupling reactions from the corresponding 2,2′-diiodobiphenyls.

Key words

metalation - copper - cross-coupling - biaryls - tetraphenylene

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References and Notes

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A more efficient two-steps synthetic route towards 2,2′-diiodobiphenyl (8, Scheme [6] )⁹:

Scheme 6

Zusatzmaterial

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