A hexafluoroisopropanol (HFIP)-promoted hydroxydifluoromethylation of aniline, indole, and pyrrole derivatives with difluoroacetaldehyde ethyl hemiacetal has been developed. This protocol provides a facile and straightforward approach to access diverse difluoromethylated carbinols in good to excellent yields under mild conditions. Furthermore, gram-scale and synthetic derivatization experiments have also been demonstrated.
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Divergent synthesis of difluoromethylated indole-3-carbinols, bisindolylmethanes and indole-3-methanamines.
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Indole-3-carbinol, bisindolylmethanes (BIMs) and indole-3-methanamines exhibit diverse therapeutic activities. Fluorinated molecules are widely used in pharmaceuticals. Herein we report a facile and straightforward method for the successful synthesis of difluoromethylated indole-3-carbinols, bisindolylmethanes and indole-3-methanamines by a Friedel-Crafts reaction.
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A facile and efficient method has been developed for the synthesis of C3-difluoromethyl carbinol-containing imidazo[1,2-]pyridines at room temperature via the HFIP-promoted Friedel-Crafts reaction of difluoroacetaldehyde ethyl hemiacetal and imidazo[1,2-]pyridines. This strategy could be applied to the direct C(sp)-H hydroxydifluoromethylation of imidazo[1,2-]pyridines and afford a series of novel difluoromethylated carbinols in good to satisfactory yields with 29 examples. Furthermore, gram-scale and synthetic transformation experiments have also been achieved, demonstrating its potential applicable value in organic synthesis.
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J Org Chem
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Advanced Research Institute and School of Pharmaceutical Sciences, Taizhou University, Jiaojiang, Zhejiang 318000, P.R. China.
A hexafluoroisopropanol (HFIP)-promoted hydroxydifluoromethylation of aniline, indole, and pyrrole derivatives with difluoroacetaldehyde ethyl hemiacetal has been developed. This protocol provides a facile and straightforward approach to access diverse difluoromethylated carbinols in good to excellent yields under mild conditions. Furthermore, gram-scale and synthetic derivatization experiments have also been demonstrated.
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