O2-Mediated transformation of 9-phenanthrenol: an approach to the synthesis of phenanthrenyl ketal and 9-fluorenones

Dongwei Wang; Zuosen Shi; Xueyou Zhang; Zhanchen Cui; Qifeng Wang

doi:10.1039/D0QO01234C

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O₂-Mediated transformation of 9-phenanthrenol: an approach to the synthesis of phenanthrenyl ketal and 9-fluorenones†

Dongwei Wang,^a Zuosen Shi,^b Xueyou Zhang,^a Zhanchen Cui

^b and Qifeng Wang

*^ab

Author affiliations

* Corresponding authors

^a International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. China
E-mail: wangqifeng@jlu.edu.cn

^b State Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. China

Abstract

We report herein a novel pathway for oxidation of 9-phenanthrenol, giving an unprecedented ketal structure. 9-Fluorenone and its derivatives can be synthesized in good to high yields with good functional group tolerance using the ketal or 9-phenanthrenols as substrates. Decomposition and formation processes of the ketal have been investigated.

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Article information

DOI: https://doi.org/10.1039/D0QO01234C
Article type: Research Article
Submitted: 09 Oct 2020
Accepted: 18 Nov 2020
First published: 19 Nov 2020

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Org. Chem. Front., 2021,8, 266-272

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O₂-Mediated transformation of 9-phenanthrenol: an approach to the synthesis of phenanthrenyl ketal and 9-fluorenones

D. Wang, Z. Shi, X. Zhang, Z. Cui and Q. Wang, Org. Chem. Front., 2021, 8, 266 DOI: 10.1039/D0QO01234C

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