4.8 Article

Light-Promoted Dearylation of Perfluorinated Aryl Sulfides with N-Heterocyclic Carbene-Borane

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ORGANIC LETTERS
卷 24, 期 46, 页码 8559-8563

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03585

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  1. Russian Science Foundation
  2. [21-73-10129]

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This study presents the removal of a tetrafluoropyridinyl group tethered to a sulfur atom using a complex of N-heterocyclic carbene (NHC) with borane. The reaction is carried out under blue light irradiation with a disulfide as a radical initiator. Selective cleavage of S-Ar bond rather than the weaker S-Alk bond is achieved through aromatic radical substitution of the thiyl group by a NHC-stabilized boron-centered radical. Alkyl thiols, the primary products of dearylation, can be in situ oxidized or alkylated to form disulfides or sulfides, respectively.
The removal of the tetrafluoropyridinyl group tethered to a sulfur atom using a complex of N-heterocyclic carbene (NHC) with borane is described. The reaction is performed under blue light irradiation with a disulfide as radical initiator. The selective cleavage of S-Ar in preference to the weaker S-Alk bond is achieved as a result of aromatic radical substitution of the thiyl group by a NHC-stabilized boron-centered radical. Alkyl thiols, which are the primary products of the dearylation, are in situ oxidized or alkylated, affording disulfides or sulfides, respectively.

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