Issue 24, 2016
From the journal:

Chemical Communications

Acid-promoted bicyclization of arylacetylenes to benzobicyclo[3.2.1]octanes through cationic rearrangements†

Xiang Su,a   Yihua Sun,b   Jiannian Yao,b   Hui Chen*b  and  Chao Chen*a  

* Corresponding authors

a Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China
E-mail: chenchao01@mails.tsinghua.edu.cn

b Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Photochemistry Institute of Chemistry, Chinese Academy of Sciences, Beijing, China
E-mail: chenh@iccas.ac.cn

Abstract

Acid-promoted efficient, site- and stereo-selective bicyclization of alkynes to polycyclic compounds (benzobicyclo[3.2.1]octanes) was realized with atom- and step-economy. The reaction proceeded through two C–C bonds formed on remote alkyl C–H bonds via twice long-distance cationic rearrangement.

Graphical abstract: Acid-promoted bicyclization of arylacetylenes to benzobicyclo[3.2.1]octanes through cationic rearrangements

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Article information

DOI
https://doi.org/10.1039/C6CC00452K
Article type
Communication
Submitted
17 Jan 2016
Accepted
26 Feb 2016
First published
26 Feb 2016

Chem. Commun., 2016,52, 4537-4540

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Acid-promoted bicyclization of arylacetylenes to benzobicyclo[3.2.1]octanes through cationic rearrangements

X. Su, Y. Sun, J. Yao, H. Chen and C. Chen, Chem. Commun., 2016, 52, 4537 DOI: 10.1039/C6CC00452K

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