Dearomatization of 3-cyanoindoles by (3 + 2) cycloaddition: from batch to flow chemistry

Literature Information

Publication Date 2020-04-20
DOI 10.1039/D0OB00582G
Impact Factor 3.876
Authors

Maxime Manneveau, Saori Tanii, Fanny Gens, Julien Legros


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Abstract

1,3-Dipolar dearomatizing cycloadditions between a non-stabilized azomethine ylide and 3-cyanoindoles or benzofuran afford the corresponding 3D-heterocycles bearing a quaternary carbon centre at the ring junction. While 6 equivalents of ylide precursor 1 are required for full conversion in a classical flask, working under flow conditions limits the excess (3 equiv., tR = 1 min) and leads to a cleaner process, affording cycloadducts that are easier to isolate.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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