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Synlett 2011(7): 1018-1022  
DOI: 10.1055/s-0030-1259708
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Concise Synthetic Approach Towards Hydroxytetraphenylenes

Jian-Fang Cuia, Hui Huanga, 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;
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Publication History

Received 10 November 2010
Publication Date:
08 March 2011 (online)

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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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1

An Area of Excellence Scheme established under the University Grants Committee (Hong Kong).

10

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

Scheme 6