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Generation of formaldehyde and formaldehyde-d₂ for hydroxymethylations and hydroxydeuteromethylations of difluoroenolates and difluorobenzyl carbanions.

ABSTRACT: 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-d₂ 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.

SUBMITTER: Khatri HR

PROVIDER: S-EPMC9205602 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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Generation of formaldehyde and formaldehyde-d2 for hydroxymethylations and hydroxydeuteromethylations of difluoroenolates and difluorobenzyl carbanions.

Khatri Hari R HR Han Changho C Alkhodier Reem A RA Adam Amna T AT Islam Baharul B Colby David A DA

Chemical communications (Cambridge, England) 20220503 36

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-d2 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. ...[more]

PMID: 35416212

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