Journal
ORGANIC LETTERS
Volume 25, Issue 44, Pages 8033-8037Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c03249
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A practical and effective method for synthesizing thioesters from readily available carboxylic acids and odorless disulfides under photocatalytic conditions was developed. This method involves phosphoranyl radical-mediated fragmentation to generate acyl radicals and incorporates both sulfur atoms of the disulfides into the desired products. In addition to batch reactions, a continuous-flow reactor was utilized for rapid gram-scale thioester synthesis. Preliminary experimental mechanistic studies and the rapid synthesis of dalcetrapib were also demonstrated.
Herein, a practical and effective synthesis of thioesters from readily available carboxylic acids and odorless disulfides was developed under photocatalytic conditions. This approach involves phosphoranyl radical-mediated fragmentation to generate acyl radicals and allows for incorporation of both S atoms of the disulfides into the desired products. In addition to batch reactions, a continuous-flow reactor was employed, enabling rapid thioester synthesis on a gram scale. Preliminary experimental mechanistic studies and the rapid synthesis of dalcetrapib are also demonstrated.
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