Selective C(sp3)-S Bond Cleavage of Thioethers to Build Up Unsymmetrical Disulfides.
J Org Chem
; 88(19): 13699-13711, 2023 Oct 06.
Article
em En
| MEDLINE
| ID: mdl-37747962
ABSTRACT
The selective C(sp3)-S bond cleavage of thioethers was first developed to prepare unsymmetrical disulfides by using electrophilic halogenation reagents. In this strategy, NBS (N-bromosuccinimide) achieves selective furfuryl C(sp3)-S bond cleavage of furfuryl alkylthioethers at room temperature. Meanwhile, NFSI (N-fluorobenzenesulfonimide) enables selective methyl C(sp3)-S bond cleavage of aryl and alkyl methylthioethers at an elevated temperature. Notably, the substrate scope investigation indicates that the order of selectivity of the C-S bond cleavage is furfuryl C(sp3)-S > benzyl C(sp3)-S > alkyl C(sp3)-S > C(sp2)-S bond. Moreover, this practical and operationally simple strategy also provides an important complementary way to access various unsymmetrical disulfides with excellent functional group tolerances and moderate to good yields.
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MEDLINE
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En
Ano de publicação:
2023
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Article