Dearomatization of 3‑Nitroindoles Enabled Using Palladium-Catalyzed Decarboxylative [4 + 2] Cycloaddition of 2‑Alkylidenetrimethylene Carbonates

A dearomatization process of 3-nitroindoles enabled using palladium-catalyzed decarboxylative [4 + 2] cycloaddition of either 2-alkylidenetrimethylene carbonates or 2-(hydroxymethyl)-3-arylallyl carbonates has been developed, affording a wide range of indoline-fused tetrahydropyrans in good yields w...

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Published inJournal of organic chemistry Vol. 87; no. 9; pp. 6025 - 6037
Main Authors Dou, Pei-Hao, Yuan, Shu-Pei, Chen, Yan, Zhao, Jian-Qiang, Wang, Zhen-Hua, You, Yong, Zhang, Yan-Ping, Zhou, Ming-Qiang, Yuan, Wei-Cheng
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 06.05.2022
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Summary:A dearomatization process of 3-nitroindoles enabled using palladium-catalyzed decarboxylative [4 + 2] cycloaddition of either 2-alkylidenetrimethylene carbonates or 2-(hydroxymethyl)-3-arylallyl carbonates has been developed, affording a wide range of indoline-fused tetrahydropyrans in good yields with excellent diastereoselectivities. This reaction features a wide substrate scope and mild conditions and represents the first example of the application of π-allyl palladium 1,4-[O,C]-dipole species for the dearomative cycloaddition of electron-deficient heteroarenes.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00276