Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 43, Pages 15381-15385Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201909786
Keywords
boranes; borenium; borylation; directing groups; electrophilic aromatic substitution
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Funding
- Horizon 2020 Research and Innovation Program [769599]
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Indoles are privileged heterocycles found in many biologically active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C-H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C-H borylation enabling selective formation of C5-BPin-indoles.
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