Metal-Free Iodine/TEMPO-Mediated Aerobic Oxidative Ugi-Type Multicomponent Reactions with Tertiary Amines.,The Journal of Organic Chemistry

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Metal-Free Iodine/TEMPO-Mediated Aerobic Oxidative Ugi-Type Multicomponent Reactions with Tertiary Amines.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-01-02 , DOI: 10.1021/acs.joc.9b03168
Dengke Li ₁ , Xianfu Shen ₁ , Jian Lei ₂

Affiliation

A novel aerobic oxidative Ugi-type multicomponent reaction (MCR) with tertiary amines was developed. The reaction was initiated by C(sp3)-H oxidation of the amine, followed by nucleophilic attack on the highly reactive isocyanide, generating nitrilium ion intermediates. If these intermediates were trapped by water in the system, α-amido amines could be delivered as the Ugi-3CR products. If exogenous TMSN3 was added, α-tetrazolo amines could be furnished as the first example of oxidative Ugi-azide MCR products.

中文翻译：

与叔胺的无金属碘/ TEMPO介导的需氧氧化Ugi型多组分反应。

开发了一种新型的与叔胺的需氧氧化Ugi型多组分反应（MCR）。通过胺的C（sp3）-H氧化引发反应，然后对高反应性异氰酸酯进行亲核攻击，生成腈离子中间体。如果这些中间体被系统中的水捕集，则α-酰胺基胺可以作为Ugi-3CR产品传递。如果添加外源TMSN3，则可以提供α-四唑胺作为氧化Ugi-叠氮化物MCR产品的第一个实例。

更新日期：2020-01-02

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