Organocatalytic Decarboxylative Borylation of Cyclopropane N-Hydroxyphthalimide Esters

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Abstract
A convenient protocol for the two-step organocatalytic decarboxylative borylation of 1,1-disubstituted, 1,2-disubstituted, and bicyclic cyclopropane carboxylic acids via the corresponding N-hydroxyphthalimide esters is described, using tert-butyl or ethyl isonicotinate as an inexpensive and readily available catalyst. The scope of the method was demonstrated, being limited mainly by electron-poor substrates. The reaction sequence showed good scalability (up to 51.5 g) and excellent trans diastereoselectivity (for the case of 1,2-disubstituted substrates). Therefore, the proposed approach is a very promising alternative to other existing (i.e., metal-catalyzed) methods for borodecarboxylation.
Funding Information
  • Ministry of Education and Science of Ukraine (0121U100387 (21BF037-01M), 0122U001962 (22BF037-02))
  • Enamine Ltd.

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