Issue 90, 2012
From the journal:

Chemical Communications

Tandem carbon–carbon bond insertion and intramolecular aldol reaction of benzyne with aroylacetones: novel formation of 4,4′-disubstituted 1,1′-binaphthols†

Kentaro Okuma,*a   Ryoichi Itoyama,a   Ayumi Sou,a   Noriyoshi Nagahoraa  and  Kosei Shioja  

* Corresponding authors

a Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan
E-mail: kokuma@fukuoka-u.ac.jp
Fax: +81-92-865-6030
Tel: +81-92-871-6631

Abstract

An efficient route to 4-aryl-2-naphthols from arynes and aroylacetones was developed by carbon–carbon bond insertion followed by an intramolecular aldol reaction and dehydration. Benzyne derived from 2-(trimethylsilyl)phenyl triflate reacted with benzoylacetones in refluxing acetonitrile to give 4-aryl-2-naphthols and 3-aryl-1-naphthols.

Graphical abstract: Tandem carbon–carbon bond insertion and intramolecular aldol reaction of benzyne with aroylacetones: novel formation of 4,4′-disubstituted 1,1′-binaphthols

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Article information

DOI
https://doi.org/10.1039/C2CC36128K
Article type
Communication
Submitted
23 Aug 2012
Accepted
25 Sep 2012
First published
26 Sep 2012

Chem. Commun., 2012,48, 11145-11147

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Tandem carbon–carbon bond insertion and intramolecular aldol reaction of benzyne with aroylacetones: novel formation of 4,4′-disubstituted 1,1′-binaphthols

K. Okuma, R. Itoyama, A. Sou, N. Nagahora and K. Shioj, Chem. Commun., 2012, 48, 11145 DOI: 10.1039/C2CC36128K

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