An efficient method for α-monofluorination of carbonyl compounds with molecular fluorine: Use of α-hydroxymethylene substituent as directing and activating groups

Add time:09/05/2019    Source:sciencedirect.com

Molecular fluorine efficiently reacts with α-hydroxymethylene carbonyl compounds to give α-fluoro-α-formyl compounds in a highly site-specific manner. The fluorinated compounds mostly isolated as their hemiacetals with methanol are readily deformylated just by treatment with weak bases affording α-monofluorinated carbonyl compounds. In this fluorination method, the hydroxymethylene group serves not only as a directing group but also as the activating group of carbonyl compounds for fluorination. By this method, a series of α-fluoro carbonyl compounds including esters was synthesized in high yields.

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