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Synthesis of gem-Difluorinated 2,3-Dihydrobenzofurans Using Freon-22 via [4 + 1] Annulation of Difluorocarbene and Antitumor Activity Evaluation

Zhou, Qianying ; Huang, Mi LU ; Shen, Yongcun ; Chen, Zhenling ; Xu, Liying and Yang, Zhigang (2024) In Organic Letters 26(6). p.1212-1217
Abstract

As an inexpensive industrial chemical, chlorodifluoromethane (Freon-22), despite its relatively low reactivity, can serve as a practical CF2 source for the construction of gem-difluorinated ring structures. Here, we develop a protocol for the efficient assembly of valuable fluorinated 2,3-dihydrobenzofurans from the [4 + 1] annulation in good yields under basic conditions. The reliable practicability and scalability of the process have also been demonstrated by preparation at the multigram scale, late-stage modifications of pharmaceutical molecules, and potential antitumor potency.

Please use this url to cite or link to this publication:
author
; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Organic Letters
volume
26
issue
6
pages
6 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • pmid:38300133
  • scopus:85184798832
ISSN
1523-7060
DOI
10.1021/acs.orglett.4c00011
language
English
LU publication?
yes
id
4f1f2780-79aa-4067-8ad2-4e2033f831f7
date added to LUP
2024-02-29 13:54:41
date last changed
2024-04-14 09:47:36
@article{4f1f2780-79aa-4067-8ad2-4e2033f831f7,
  abstract     = {{<p>As an inexpensive industrial chemical, chlorodifluoromethane (Freon-22), despite its relatively low reactivity, can serve as a practical CF<sub>2</sub> source for the construction of gem-difluorinated ring structures. Here, we develop a protocol for the efficient assembly of valuable fluorinated 2,3-dihydrobenzofurans from the [4 + 1] annulation in good yields under basic conditions. The reliable practicability and scalability of the process have also been demonstrated by preparation at the multigram scale, late-stage modifications of pharmaceutical molecules, and potential antitumor potency.</p>}},
  author       = {{Zhou, Qianying and Huang, Mi and Shen, Yongcun and Chen, Zhenling and Xu, Liying and Yang, Zhigang}},
  issn         = {{1523-7060}},
  language     = {{eng}},
  number       = {{6}},
  pages        = {{1212--1217}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Organic Letters}},
  title        = {{Synthesis of gem-Difluorinated 2,3-Dihydrobenzofurans Using Freon-22 via [4 + 1] Annulation of Difluorocarbene and Antitumor Activity Evaluation}},
  url          = {{http://dx.doi.org/10.1021/acs.orglett.4c00011}},
  doi          = {{10.1021/acs.orglett.4c00011}},
  volume       = {{26}},
  year         = {{2024}},
}