Enantioselective α-Allylation of Anilines Enabled by a Combined Palladium and Photoredox Catalytic System,ACS Catalysis

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Enantioselective α-Allylation of Anilines Enabled by a Combined Palladium and Photoredox Catalytic System
ACS Catalysis ( IF 11.3 ) Pub Date : 2020-03-24 , DOI: 10.1021/acscatal.0c00871
Hong-Hao Zhang ₁ , Jia-Jia Zhao ₁ , Shouyun Yu ₁

Affiliation

An enantioselective and branch-regioselective α-allylation of N-methyl anilines under dual palladium/photoredox catalysis is described. Readily available N-methyl anilines are used as formal “hard” alkyl nucleophiles without preactivation. Acetic acid is the only side product, which leads to a high atom economy of this reaction. This protocol shows good functional group tolerance and broad scope. A range of chiral homoallylic amines were prepared in moderate to good yields (up to 76%) and excellent regioselectivities (B:L > 95:5 in all cases) and enantioselectivities (up to 96% ee) under mild reaction conditions.

中文翻译：

钯和光氧化还原催化体系共同作用的苯胺对映体选择性α-烯丙基化

描述了在钯/光氧化还原双重催化下N-甲基苯胺的对映选择性和支链区域选择性α-烯丙基化。易于获得的N-甲基苯胺不经预活化即可用作正式的“硬”烷基亲核试剂。乙酸是唯一的副产物，其导致该反应的高原子经济性。该协议显示了良好的功能组耐受性和广泛的范围。在温和的反应条件下，以中等至良好的收率（最高76％），极好的区域选择性（在所有情况下B：L> 95：5）和对映体选择性（最高96％ee）制备了一系列手性均胺。

更新日期：2020-04-23

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