Multigram Deoxofluorination of β-Keto Esters with Sulfur Tetrafluoride

Semi-Industrial Fluorination of β-Keto Esters with SF4: Safety vs Efficacy: S. A. Trofymchuk, D. V. Kliukovskyi, S. V. Semenov, A. R. Khairulin, V. O. Shevchenko, M. Y. Bugera, K. V. Tarasenko, D. M. Volochnyuk, S. V. Ryabukhin
Synlett 2020, 31, DOI: 10.1055/s-0037-1610744


Selectively fluorinated building blocks are increasingly important in drug discovery owing to the prominent role of fluoroorganic compounds as pharmaceuticals. The deoxofluorination of carbonyl compounds with fluorinating agents such as DAST or the more reactive SF4 is a workhorse of organofluorine chemistry, but the choice of the right reagent and conditions is often a challenging endeavor for organic chemists, especially on a large scale. Now, in a joint effort involving Enamine Ltd. (Kyiv, Ukraine) and Taras Shevchenko National University of Kyiv (Ukraine), led by Professors Dmitriy M. Volochnyuk and Sergey V. Ryabukhin, pros and cons of using DAST vs SF4 for the multigram preparation of 3,3-difluoroesters have been investigated.

Professors Volochnyuk and Ryabukhin said: “Development of new safe synthetic methods using hazardous reagents (e.g. SF4), which allows to increase efficiency of production of relevant building blocks in medicinal chemistry, is an important practical task of modern organic chemistry.”

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