Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 18, Pages 11665-11675Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01595
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Funding
- National Institutes of Health (NIH)
- National Institute on Aging [R21AG039718]
- National Institute of General Medical Sciences [P20GM104932]
- Ralph W. and Grace M. Showalter Research Trust funds
- Department of Energy Office of Science [DE-SC0011297]
- OU startup fund
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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 alpha,alpha-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 alpha,alpha-difluorobenzyl carbanions from electron-deficient aromatics and heteroaromatic rings can react with aldehydes to create derivatives of difluoromethylbenzenes, which are valuable synthetic targets.
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