Journal
ACS CATALYSIS
Volume 10, Issue 11, Pages 6023-6029Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c00872
Keywords
hydroarylation; aniline; alkene; HFIP; mefenamic acid
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Funding
- Juan de la Cierva fellowship from the Spanish Ministry of Science [IJCI-2016-27405]
- La Caixa Foundation under the Junior Leader Program [LCF/BQ/PI19/11690020, 100010434]
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Providing new methods for the selective functionalization of small molecules is highly desirable, because installing molecular diversity in a desired position, for example, allows one to modulate bioactive molecules. This work reports a method for the selective functionalization of anilines using hexafluoroisopropanol (HFIP) as a solvent to promote an acid-catalyzed hydroarylation of olefins. Mechanistic experiments revealed that HFIP both protonates the alkene and selectively enables anilines toward the electrophilic aromatic substitution. This powerful strategy has been applied to the functionalization of the anti-inflammatory mefenamic acid with chemocontrol and regiocontrol.
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