Development and Kilogram-Scale Implementation of a Flavin-Catalyzed Photoredox Fluorodecarboxylation

Photo high-throughput experimentation (photo-HTE) and design of experiment (DoE)-guided optimization have enabled the discovery of efficient, homogeneous, and cost-effective conditions for fluorodecarboxylation of carboxylic acids. Our flavin-catalyzed fluorodecarboxylation process has been demonstr...

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Bibliographic Details
Published inOrganic process research & development Vol. 28; no. 1; pp. 266 - 272
Main Authors Jerkovic, Tatjana, Cruickshank, Harriet, Chen, Yiding, Trindade, Alexandre F., Dumas, Aaron M., Edwards, John, Alorati, Anthony, Ho, Hon Eong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.01.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
fluorination
photoredox
scale-up photochemistry
high-throughput experimentation
design of experiments
flow chemistry
UV
REACTOR
DECARBOXYLATIVE FLUORINATION
scale-upphotochemistry
LIGHT
ALIPHATIC CARBOXYLIC-ACIDS
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Summary:Photo high-throughput experimentation (photo-HTE) and design of experiment (DoE)-guided optimization have enabled the discovery of efficient, homogeneous, and cost-effective conditions for fluorodecarboxylation of carboxylic acids. Our flavin-catalyzed fluorodecarboxylation process has been demonstrated on 1.5 kg scale under continuous flow for 4.5 h at 100 mL/min (∼5 min residence time), achieving an overall yield of 92% (1.23 kg), equating to 6.56 kg/day throughput.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.3c00342