Issue 11, 2008
From the journal:

Organic & Biomolecular Chemistry

Hydroindation of allenes and its application to radical cyclization†

Naoki Hayashi,a   Yusuke Hirokawa,a   Ikuya Shibata,*b   Makoto Yasudaa  and  Akio Baba*a  

* Corresponding authors

a Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka, Japan
E-mail: baba@chem.eng.osaka-u.ac.jp
Fax: +81-6-6879-7387
Tel: +81-6-6879-7386

b Research Center for Environmental Preservation, Osaka University, 2-4 Yamadaoka, Suita, Osaka, Japan
E-mail: shibata@epc.osaka-u.ac.jp
Fax: +81-6-6879-8978
Tel: +81-6-6879-8974

Abstract

Hydroindation of allenes and radical cyclization of 1,2,7-trienes (allenenes) were accomplished by HInCl2 with high regioselectivity to afford a variety of cyclic compounds. The resulting vinylic indiums could be used for successive coupling reactions in a one-pot procedure. The use of HInCl2 generated slowly in situ is extremely effective for the radical cyclization.

Graphical abstract: Hydroindation of allenes and its application to radical cyclization

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Article information

DOI
https://doi.org/10.1039/B803314E
Article type
Paper
Submitted
26 Feb 2008
Accepted
11 Mar 2008
First published
09 Apr 2008

Org. Biomol. Chem., 2008,6, 1949-1954

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Hydroindation of allenes and its application to radical cyclization

N. Hayashi, Y. Hirokawa, I. Shibata, M. Yasuda and A. Baba, Org. Biomol. Chem., 2008, 6, 1949 DOI: 10.1039/B803314E

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