Nickel‐Catalyzed Three‐Component Coupling Reactions of Iodobenzenes, an Isocyanide, and a Disilathiane: Access to Cyclic Thioimidates and Secondary Thioamides

We demonstrate that a Ni(II)/ t ‐BuOK catalytic system effectively catalyzes the three‐component coupling (TCC) reactions of 2‐ethynyliodobenzenes, t ‐butyl isocyanide, and hexamethyldisilathiane to produce various 3‐benzylidene‐ N ‐( t ‐butyl)benzo[ c ]thiophen‐1‐imine derivatives with a cyclic thioimidate skeleton. The disilathiane was successfully utilized as the sulfur source and can be embedded in a ring structure. Moreover, iodobenzene can undergo the same intermolecular TCC reactions, effectively affording secondary thioamide derivatives.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2026-04-20
DOI
https://doi.org/10.1002/ejoc.70459
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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0.00

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article

Nickel‐Catalyzed Three‐Component Coupling Reactions of Iodobenzenes, an Isocyanide, and a Disilathiane: Access to Cyclic Thioimidates and Secondary Thioamides

Kento Ishida, Norio Sakai, Yohei Ogiwara, Reo Ikeda et al.
European Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Nickel‐Catalyzed Three‐Component Coupling Reactions of Iodobenzenes, an Isocyanide, and a Disilathiane: Access to Cyclic Thioimidates and Secondary Thioamides

Kento Ishida, Norio Sakai, Yohei Ogiwara, Reo Ikeda, Shun Nishitai
article en

Abstract

We demonstrate that a Ni(II)/ t ‐BuOK catalytic system effectively catalyzes the three‐component coupling (TCC) reactions of 2‐ethynyliodobenzenes, t ‐butyl isocyanide, and hexamethyldisilathiane to produce various 3‐benzylidene‐ N ‐( t ‐butyl)benzo[ c ]thiophen‐1‐imine derivatives with a cyclic thioimidate skeleton. The disilathiane was successfully utilized as the sulfur source and can be embedded in a ring structure. Moreover, iodobenzene can undergo the same intermolecular TCC reactions, effectively affording secondary thioamide derivatives.

European Journal of Organic Chemistry
Tokyo University of Science (JP)
Japan Society for the Promotion of Science
Openalex Percentile: Top 9%
Catalytic C–H Functionalization Methods
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