Unknown

Dataset Information

0

Controlling the Cleavage of Carbon-Carbon Bonds To Generate α,α-Difluorobenzyl Carbanions for the Construction of Difluoromethylbenzenes.


ABSTRACT: Controlling the cleavage of carbon-carbon bonds during a chemical reaction is a substantial challenge; however, synthetic methods that accomplish this objective produce valuable and often unexplored reactivity. We have designed a mild process to generate α,α-difluorobenzyl carbanions in the presence of potassium carbonate by exploiting the cleavage of C-C bonds during the release of trifluoroacetate. The initiating reagent is potassium carbonate, which represents an improvement over existing protocols that require a strong base. Fragmentation studies across substituted arenes and heteroarenes were conducted along with computational analyses to elucidate reactivity trends. Furthermore, the mildly generated α,α-difluorobenzyl carbanions from electron-deficient aromatics and heteroaromatic rings can react with aldehydes to create derivatives of difluoromethylbenzenes, which are valuable synthetic targets.

SUBMITTER: Khatri HR 

PROVIDER: S-EPMC8262649 | biostudies-literature |

REPOSITORIES: biostudies-literature

Similar Datasets

| S-EPMC6679931 | biostudies-literature
| S-EPMC4353009 | biostudies-literature
| S-EPMC3384763 | biostudies-literature
| S-EPMC5477049 | biostudies-literature
| S-EPMC8652261 | biostudies-literature
| S-EPMC7047910 | biostudies-literature
| S-EPMC124047 | biostudies-literature
| S-EPMC8457114 | biostudies-literature
| S-EPMC5502808 | biostudies-literature
| S-EPMC6818169 | biostudies-literature