What question did this study set out to answer?

The research aims to explore a nickel-catalyzed system for synthesizing cyclic thioimidates and thioamides from iodobenzenes and isocyanides.

April 22, 2026Open Access

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

Key Points

The research aims to explore a nickel-catalyzed system for synthesizing cyclic thioimidates and thioamides from iodobenzenes and isocyanides.
Utilized a Ni(II)/t-BuOK catalytic system for three-component coupling reactions.
Employed 2-ethynyliodobenzenes, t-butyl isocyanide, and hexamethyldisilathiane as reactants.
Characterized products, including cyclic thioimidate derivatives and secondary thioamides.
Successfully synthesized various 3-benzylidene-N-(t-butyl)benzo[c]thiophen-1-imine derivatives.
Showed that disilathiane serves as a sulfur source in the reaction.
Demonstrated that iodobenzene can participate in similar intermolecular coupling reactions.

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.

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Cite This Study

Sakai et al. (Mon,) studied this question.

synapsesocial.com/papers/69e866f16e0dea528ddeb490 https://doi.org/https://doi.org/10.1002/ejoc.70459

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