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Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent.

ABSTRACT: This manuscript describes the electrochemical synthesis of 17 different glycosyl fluorides in 73-98% yields on up to a 5 g scale that relies on the use of SF₆ as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF₆ are transient under these reductive conditions and that the sulfur and fluoride byproducts are effectively scavenged by Zn(II) to generate benign salts.

SUBMITTER: Kim S

PROVIDER: S-EPMC10543653 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent.

Kim Sungjin S Nagorny Pavel P

Organic letters 20220317 12

This manuscript describes the electrochemical synthesis of 17 different glycosyl fluorides in 73-98% yields on up to a 5 g scale that relies on the use of SF<sub>6</sub> as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF<sub>6</sub> are transient under these reductive conditions and that the sulfur and fluoride byproducts are effectiv ...[more]

PMID: 35298181

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