Issue 23, 2020
From the journal:

Organic Chemistry Frontiers

Metal-free synthesis of 3-chalcogenyl chromones from alkynyl aryl ketones and diorganyl diselenides/disulfides mediated by PIFA†

Zhenkang Ai,a   Jiaxi Xiao,a   Yadong Li,a   Boying Guo,b   Yunfei Du ORCID logo *a  and  Kang Zhao*c  

* Corresponding authors

a School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China
E-mail: duyunfeier@tju.edu.cn

b Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA

c State Key Laboratory of Microbial Technology, Institute of Microbial Technology, Shandong University, Qingdao 266237, China
E-mail: zhaokang@sdu.edu.cn

Abstract

3-Selenyl/sulfenyl chromones/thiochromones were conveniently synthesized from the PIFA-mediated reactions between alkynyl aryl ketones bearing an ortho-methoxy/methylthio group and diorganyl diselenides/disulfides. This metal-free approach is postulated to first undergo the formation of the reactive RSeOCOCF3 or RSOCOCF3 from the reaction of diorganyl diselenides or disulfides with PIFA, followed by the electrophilic cyclization of alkynyl aryl ketones enabled by the electrophilic species generated herein.

Graphical abstract: Metal-free synthesis of 3-chalcogenyl chromones from alkynyl aryl ketones and diorganyl diselenides/disulfides mediated by PIFA

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Article information

DOI
https://doi.org/10.1039/D0QO01175D
Article type
Research Article
Submitted
24 Sep 2020
Accepted
23 Oct 2020
First published
26 Oct 2020

Org. Chem. Front., 2020,7, 3935-3940

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Metal-free synthesis of 3-chalcogenyl chromones from alkynyl aryl ketones and diorganyl diselenides/disulfides mediated by PIFA

Z. Ai, J. Xiao, Y. Li, B. Guo, Y. Du and K. Zhao, Org. Chem. Front., 2020, 7, 3935 DOI: 10.1039/D0QO01175D

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