Highly Enantioselective\nDecarboxylative Difluoromethylation

Organofluorine molecules that contain difluoro­methyl\ngroups\n(CF<sub>2</sub>H) at stereo­genic centers have gained importance\nin pharmaceuticals due to the unique ability of CF<sub>2</sub>H groups\nto act as lipophilic hydrogen bond donors. Despite their potential,\nthe enantio­selective installation of CF<sub>2</sub>H groups\ninto readily available starting materials remains a challenging and\nunderdeveloped area. In this study, we report a nickel-catalyzed decarboxylative\ndifluoro­methylation reaction that converts alkyl carboxylic\nacids into difluoro­methylated products with exceptional enantio­selectivity.\nThis Ni-catalyzed protocol exhibits broad functional group tolerance\nand is applicable for synthesizing fluorinated bioisosteres of biologically\nrelevant molecules.

Publication Details

Journal
Figshare
Published
2024-10-15
DOI
https://doi.org/10.1021/jacs.4c11257.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
Field-Weighted Citation Impact
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article

Highly Enantioselective\nDecarboxylative Difluoromethylation

Figshare
Mycorrhizal Fungi and Plant Interactions
article

Highly Enantioselective\nDecarboxylative Difluoromethylation

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Abstract

Organofluorine molecules that contain difluoro­methyl\ngroups\n(CF<sub>2</sub>H) at stereo­genic centers have gained importance\nin pharmaceuticals due to the unique ability of CF<sub>2</sub>H groups\nto act as lipophilic hydrogen bond donors. Despite their potential,\nthe enantio­selective installation of CF<sub>2</sub>H groups\ninto readily available starting materials remains a challenging and\nunderdeveloped area. In this study, we report a nickel-catalyzed decarboxylative\ndifluoro­methylation reaction that converts alkyl carboxylic\nacids into difluoro­methylated products with exceptional enantio­selectivity.\nThis Ni-catalyzed protocol exhibits broad functional group tolerance\nand is applicable for synthesizing fluorinated bioisosteres of biologically\nrelevant molecules.

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Openalex Percentile: Top 64%
Mycorrhizal Fungi and Plant Interactions
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