Issue 96, 2020
From the journal:

Chemical Communications

Phenanthrenes/dihydrophenanthrenes: the selectivity controlled by different benzynes and allenes†

Liangliang Yao,a   Bo Fang,a   Qiong Hu,a   Yu Lei,a   Li Baoa  and  Yimin Hu ORCID logo *a  

* Corresponding authors

a Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecular-Based Materials, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China
E-mail: yiminhu@ahnu.edu.cn

Abstract

A method for the intermolecular annulation of benzynes with allenes is disclosed. This protocol utilized allenes as an unconventional diene component for the selective synthesis of phenanthrenes and dihydrophenanthrenes under the control of different benzyne precursors, featuring high atom-economy and good functional group compatibility. Density functional theory (DFT) calculations reveal that different migratory routes of the aromatic C–H bond are crucial for the observed selectivity.

Graphical abstract: Phenanthrenes/dihydrophenanthrenes: the selectivity controlled by different benzynes and allenes

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Article information

DOI
https://doi.org/10.1039/D0CC06300B
Article type
Communication
Submitted
18 Sep 2020
Accepted
10 Nov 2020
First published
11 Nov 2020

Chem. Commun., 2020,56, 15185-15188

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Phenanthrenes/dihydrophenanthrenes: the selectivity controlled by different benzynes and allenes

L. Yao, B. Fang, Q. Hu, Y. Lei, L. Bao and Y. Hu, Chem. Commun., 2020, 56, 15185 DOI: 10.1039/D0CC06300B

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