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

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Synthesis of gem-Difluorinated 2,3-Dihydrobenzofurans Using Freon-22 via [4 + 1] Annulation of Difluorocarbene and Antitumor Activity Evaluation
Organic Letters ( IF 4.9 ) Pub Date : 2024-02-01 , DOI: 10.1021/acs.orglett.4c00011
Qianying Zhou _{1,

2} , Mi Huang ₃ , Yongcun Shen ₁ , Zhenling Chen ₄ , Liying Xu ₂ , Zhigang Yang ₂

Affiliation

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.

中文翻译：

Freon-22二氟卡宾[4+1]成环合成偕二氟化2,3-二氢苯并呋喃及抗肿瘤活性评价

作为一种廉价的工业化学品，二氟氯甲烷(Freon-22)尽管其反应性相对较低，但可以作为构建宝石二氟化环结构的实用CF ₂源。在这里，我们开发了一种在基本条件下以良好产率从 [4 + 1] 环化有效组装有价值的氟化 2,3-二氢苯并呋喃的方案。数克规模的制备、药物分子的后期修饰以及潜在的抗肿瘤效力也证明了该工艺的可靠实用性和可扩展性。

更新日期：2024-02-01

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