Photocatalytic Thiol-Yne Reactions of Alkynyl Sulfides.
J Org Chem
; 88(24): 17257-17265, 2023 Dec 15.
Article
em En
| MEDLINE
| ID: mdl-38019972
ABSTRACT
Thiol-yne reactions typically employ thiols and terminal alkynes as the reaction partners. The thiol-yne reaction of alkynyl sulfides and thiols is possible when employing a nonmetal photocatalyst eosin Y, green LED irradiation, under an air atmosphere. Alkynyl sulfides were transformed in good overall yields (58-90% total yields, 11 examples) favoring the cis isomer. No addition to the α-position of the alkynyl sulfide is observed, and regioselectivity is believed to be controlled through the stabilization of radical intermediates by the adjacent sulfur atom. Furthermore, control experiments with "all-carbon" internal alkynes demonstrate that alkynyl sulfides possess improved reactivity and regioselectivity profiles during thiol-yne processes.
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MEDLINE
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En
Ano de publicação:
2023
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Article