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Updated: Jan 17, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
External base-free electrophilic diynylation of thiols with diynyl benziodoxolone
Ryusei Uozumi1, Takuto Naito1, Hiroyoshi Esaki2
1Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan. ntada@gifu-pu.ac.jp.
Abstract:
In this study, external base-free electrophilic diynylation of thiols to 1,3-butadiynyl sulfide, an important structural motif in organic synthesis, chemical biology, and materials science using triisopropylsilyl diynyl benziodoxolone at room temperature has been developed. Various thiols, such as cysteine and thioglucopyranose derivatives and captopril, were converted into the corresponding 1,3-butadiynyl sulfides. Control experiments and a computational study were performed to investigate the reaction mechanism. The resulting 1,3-butadiynyl sulfides were further derivatized to thiobitriazole via double azide-alkyne cycloaddition and to cyclobutene via [2 + 2] cycloaddition.
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