Dearomatization of 3-Nitroindoles Enabled Using Palladium-Catalyzed Decarboxylative [4+2] Cycloaddition of2-Alkylidenetrimethylene Carbonates
Dearomatization of 3-Nitroindoles Enabled Using Palladium-Catalyzed Decarboxylative [4+2] Cycloaddition of2-Alkylidenetrimethylene Carbonates
复制标题
使用钯催化脱羧剂实现 3-硝基吲哚的脱芳构化 [4 2] 2-亚烷基三亚甲基碳酸酯的环加成
DOI：
10.1021/acs.joc.2c00276
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发表时间：
2022-05-06
影响因子：
3.6
通讯作者：
Yuan, Wei-Cheng
中科院分区：
文献类型：
--
作者：
Dou, Pei-Hao;Yuan, Shu-Pei;Yuan, Wei-Cheng
研究了钯催化的2-亚烷基三亚甲基碳酸酯和2-（羟甲基）-3-芳基烯丙基碳酸酯的脱羧[4 + 2]环加成反应对3-硝基吲哚的脱芳构化反应，得到了一系列吲哚啉稠合四氢吡喃，产率高，非对映选择性好。该反应具有底物范围广、反应条件温和的特点，是首次将π-烯丙基钯1，4-[O，C]偶极物种应用于缺电子杂芳烃的脱芳环加成反应。
A dearomatization process of 3-nitroindoles enabled using palladium-catalyzed decarboxylative [4 + 2] cycloadditionof either 2-alkylidenetrimethylene carbonates or 2-(hydroxymethyl)-3-arylallyl carbonates has been developed, affording a widerange of indoline-fused tetrahydropyrans in good yields with excellent diastereoselectivities. This reaction features a wide substratescope and mild conditions and represents thefirst example of the application of pi-allyl palladium 1,4-[O,C]-dipole species for thedearomative cycloaddition of electron-deficient heteroarenes.