Synthesis of gem-Difluorinated 2,3-Dihydrobenzofurans Using Freon-22 via [4 + 1] Annulation of Difluorocarbene and Antitumor Activity Evaluation
(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.
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https://lup.lub.lu.se/record/4f1f2780-79aa-4067-8ad2-4e2033f831f7
- author
- Zhou, Qianying ; Huang, Mi LU ; Shen, Yongcun ; Chen, Zhenling ; Xu, Liying and Yang, Zhigang
- organization
- publishing date
- 2024-02
- 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
-
- scopus:85184798832
- pmid:38300133
- 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
- 2024-07-07 17:06:25
@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}}, }