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

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

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2022, Volume: 24, Number: 46, Pages: 8559-8563 Pages count : 5 DOI: 10.1021/acs.orglett.2c03585

Authors

Panferova Liubov I. ¹ , Zubkov Mikhail O. ¹ , Kosobokov Mikhail D. ¹ , Dilman Alexander D. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Leninsky Prospekt 47, 119991 Moscow, Russian Federation

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.

Panferova L.I. , Zubkov M.O. , Kosobokov M.D. , Dilman A.D.
Light-Promoted Dearylation of Perfluorinated Aryl Sulfides with N-Heterocyclic Carbene–Borane
Organic Letters. 2022. V.24. N46. P.8559-8563. DOI: 10.1021/acs.orglett.2c03585 WOS Scopus OpenAlex

Web of science:	WOS:000885284900001
Scopus:	2-s2.0-85142004315
OpenAlex:	W4308624857

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Scopus	6
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