Copper(0)-Catalyzed Reductive Coupling of Disulfurating Reagents and (Hetero)aryl/Alkyl Halides

Herein, we reported a copper(0)-catalyzed reductive coupling of disulfurating reagents and (hetero)­aryl/alkyl halides. Copper(0) can be directly inserted into tetrasulfide and then undergoes reductive coupling with (hetero)­aryl Iodides to construct disulfide. The method features the unprecedented...

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Published inOrganic letters Vol. 26; no. 38; pp. 8115 - 8120
Main Authors Chen, Wang, Xu, Jiuwen, Rao, Weidong, Shen, Shu-Su, Yang, Zhao-Ying, Ackermann, Lutz, Wang, Shun-Yi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.09.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
copper
cross-coupling reactions
disulfides
drugs
Physical Sciences
Science & Technology
DESIGN
DITHIOLOPYRROLONES
PRODRUG
DISULFIDE
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Summary:Herein, we reported a copper(0)-catalyzed reductive coupling of disulfurating reagents and (hetero)­aryl/alkyl halides. Copper(0) can be directly inserted into tetrasulfide and then undergoes reductive coupling with (hetero)­aryl Iodides to construct disulfide. The method features the unprecedented use of copper(0)-catalyzed disulfurating reagents (tetrasulfides) in cross-coupling chemistry and is convenient with broad substrate scopes, even applicable to different halogenated hydrocarbons. It is worth noting that the methodology is practical with the late-stage modification of bioactive scaffolds of pharmaceuticals. In the meantime, the synthesis of disulfides is successfully achieved on a gram scale, indicating the approach is highly valuable.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03032