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Metal-free intermolecular formal cycloadditions enable an orthogonal access to nitrogen heterocycles.


ABSTRACT: Nitrogen-containing heteroaromatic cores are ubiquitous building blocks in organic chemistry. Herein, we present a family of metal-free intermolecular formal cycloaddition reactions that enable highly selective and orthogonal access to isoquinolines and pyrimidines at will. Applications of the products are complemented by a density functional theory mechanistic analysis that pinpoints the crucial factors responsible for the selectivity observed, including stoichiometry and the nature of the heteroalkyne.

SUBMITTER: Xie LG 

PROVIDER: S-EPMC4796318 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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Metal-free intermolecular formal cycloadditions enable an orthogonal access to nitrogen heterocycles.

Xie Lan-Gui LG   Niyomchon Supaporn S   Mota Antonio J AJ   González Leticia L   Maulide Nuno N  

Nature communications 20160315


Nitrogen-containing heteroaromatic cores are ubiquitous building blocks in organic chemistry. Herein, we present a family of metal-free intermolecular formal cycloaddition reactions that enable highly selective and orthogonal access to isoquinolines and pyrimidines at will. Applications of the products are complemented by a density functional theory mechanistic analysis that pinpoints the crucial factors responsible for the selectivity observed, including stoichiometry and the nature of the hete  ...[more]

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