Generation of formaldehyde and formaldehyde-d for hydroxymethylations and hydroxydeuteromethylations of difluoroenolates and difluorobenzyl carbanions

A method for the in situ production of formaldehyde from dimethylsulfoxide, bromine, and cesium carbonate is reported for reactions with difluoroenolates and difluorobenzyl carbanions. This process also generates formaldehyde-d 2 for the production of 2,2-difluoro-1,1-deuteroethanols. Mechanistic an...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-05, Vol.58 (36), p.549-5493
Main Authors: Khatri, Hari R, Han, Changho, Alkhodier, Reem A, Adam, Amna T, Islam, Baharul, Colby, David A
Format: Article
Language:English
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Summary:A method for the in situ production of formaldehyde from dimethylsulfoxide, bromine, and cesium carbonate is reported for reactions with difluoroenolates and difluorobenzyl carbanions. This process also generates formaldehyde-d 2 for the production of 2,2-difluoro-1,1-deuteroethanols. Mechanistic and computational studies further characterize the production of hydroxymethylated and hydroxydeuteromethylated difluorinated organic molecules. A method for the in situ production of formaldehyde from dimethylsulfoxide, bromine, and cesium carbonate is reported for reactions with difluoroenolates and difluorobenzyl carbanions.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc01518h