Issue 18, 2012
From the journal:

Organic & Biomolecular Chemistry

Palladium(0)-catalyzed cyclization of 1,6-diyn-3-yl carbonates with a nucleophilic functionality: efficient synthesis of polycyclic benzo[b]fluorene derivatives viaallene intermediates†

Shugao Zhu,a   Luling Wu*a  and  Xian Huang‡ab  

* Corresponding authors

a Department of Chemistry, Zhejiang University, Hangzhou 310028, P.R. China
E-mail: Wululing@zju.edu.cn

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P.R. China

Abstract

We report in this paper an interesting tandem reaction involving sequential palladium(0)-catalyzed decarboxylation of diynylic carbonates, intramolecular nucleophilic cyclization and Schmittel reaction, which provides a facile method for the synthesis of a variety of polycyclic benzo[b]fluorene derivatives from easily accessible starting materials.

Graphical abstract: Palladium(0)-catalyzed cyclization of 1,6-diyn-3-yl carbonates with a nucleophilic functionality: efficient synthesis of polycyclic benzo[b]fluorene derivatives via allene intermediates

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Article information

DOI
https://doi.org/10.1039/C2OB07148G
Article type
Paper
Submitted
21 Dec 2011
Accepted
01 Mar 2012
First published
05 Mar 2012

Org. Biomol. Chem., 2012,10, 3696-3704

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Palladium(0)-catalyzed cyclization of 1,6-diyn-3-yl carbonates with a nucleophilic functionality: efficient synthesis of polycyclic benzo[b]fluorene derivatives via allene intermediates

S. Zhu, L. Wu and X. Huang, Org. Biomol. Chem., 2012, 10, 3696 DOI: 10.1039/C2OB07148G

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