Meta-, Regioselective Amination of Cyclic Diaryliodoniums through C-I and C-O Bond Cleavages: An Access to Functionalized Coumarins.

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2025-03-07 Epub Date: 2025-02-26 DOI:10.1021/acs.joc.4c02094
Jiadi Li, Bingling Luo, Peisen Huang, Yameng Sun, Peng Huang, Shijun Wen, Daqian Zhu
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Abstract

Despite the widespread ortho-functionalization of cyclic diaryliodoniums in organic chemistry, the corresponding meta-functionalization is less explored. Herein, we report a practical meta-selective activation of cyclic hypervalent iodoniums for the synthesis of 4-amino coumarin derivatives in a broad functional group tolerance and environmentally friendly manner. The practicability of this protocol was further highlighted by the late-stage modification of some common pharmaceuticals and natural products.

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通过C-I和C-O键裂解环二芳基碘酮的间区选择性胺化:获得功能化香豆素的途径。
尽管环二芳基碘鎓在有机化学中广泛存在正官能化,但其相应的元官能化却很少被探索。在此,我们报道了一种实用的环高价碘的元选择性活化,以广泛的官能团耐受性和环境友好的方式合成4-氨基香豆素衍生物。一些常见药物和天然产物的后期修改进一步突出了该议定书的实用性。
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来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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