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Synthesis 2018; 50(07): 1482-1492
DOI: 10.1055/s-0036-1591021
paper
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of Functionalized 4H-Chromenes via an Fe(OTf)3-Catalyzed Cyclization Reaction of Phenols and Ketones

Kai Deng
a   School of Marine Science and Technology, Harbin Institute of Technology, Weihai 264209, P. R. of China
,
Qi-Yong Huai
b   Marine College, Shandong University, Weihai 264209, P. R. of China
,
Hui-Jing Li*
a   School of Marine Science and Technology, Harbin Institute of Technology, Weihai 264209, P. R. of China
,
Jun-Hu Wang
a   School of Marine Science and Technology, Harbin Institute of Technology, Weihai 264209, P. R. of China
,
Hui-Ru Yang
a   School of Marine Science and Technology, Harbin Institute of Technology, Weihai 264209, P. R. of China
,
Ying Liu
a   School of Marine Science and Technology, Harbin Institute of Technology, Weihai 264209, P. R. of China
,
Yan-Chao Wu  *
a   School of Marine Science and Technology, Harbin Institute of Technology, Weihai 264209, P. R. of China
c   Beijing National Laboratory for Molecular Sciences, Institute of Chemistry Chinese Academy of Sciences, Beijing 100190, P. R. of China   Email: ycwu@iccas.ac.cn
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (21672046, 21372054), the Fundamental Research Funds for the Central Universities (HIT.NSRIF.201701, 201708), and the Natural Science Foundation of Shandong (2015ZRA10064).
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Publication History

Received: 20 November 2017

Accepted: 10 December 2017

Publication Date:
11 January 2018 (online)

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Abstract

The iron(III) triflate catalyzed cyclization reaction of phenols and ketones is described; the reaction provides a direct approach to 4H-chromene derivatives. 4H-Chromene is an important structural fragment of many pharmaceuticals, natural products, and functional materials. The 4H-chromene synthetic protocol possesses many advantages, such as using readily available and inexpensive starting materials and a non-toxic catalyst, high selectivity, and operational simplicity, which offer­ attractive industrial prospects from the point of view of green and sustainable chemistry.

Key words

iron catalyst - 4H-chromene - cyclization reaction - synthesis - 4H-1-benzopyran

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-00xx-xxxxxxx.
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