Dearomatization of 3-cyanoindoles by (3 + 2) cycloaddition: from batch to flow chemistry
Maxime Manneveau1, Saori Tanii, Fanny Gens
1Normandie Université, UNIROUEN, CNRS, INSA Rouen, COBRA laboratory, F-76000 Rouen, France. julien.legros@univ-rouen.fr isabelle.chataigner@univ-rouen.fr.
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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