Nickel-Catalyzed Hydrocarbamoylation of Alkenes with Isocyanates

The hydrocarbamoylation of alkenes with isocyanates is a promising method for synthesizing amides. However, applying this strategy to more inert, simple alkenes, such as styrenes, α-olefins, and internal alkenes, poses significant challenges. Here, we report the first nickel-catalyzed hydrocarbamoylation of alkenes with isocyanates, facilitated by triethoxysilane to reduce nickelacycle intermediates. By switching ligands─including 6,6'-dimethyl-2,2'-bipyridine and <i>N</i>-heterocyclic carbene─this method efficiently produces amides from a diverse array of alkenes, including styrenes, α-olefins, internal alkenes, and gaseous olefins.

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Publication Details

Journal
Organic Letters
Published
2025-03-17
DOI
https://doi.org/10.1021/acs.orglett.5c00520
Citations
6
Primary Topic
Chemical Synthesis and Reactions
Type
article
Field-Weighted Citation Impact
5.62

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article

Nickel-Catalyzed Hydrocarbamoylation of Alkenes with Isocyanates

Li‐Jun Xiao, Qi‐Lin Zhou, Yuqing Wang, Meng-Ying Qian
6 citations
Organic Letters
Chemical Synthesis and Reactions
5.62
article

Nickel-Catalyzed Hydrocarbamoylation of Alkenes with Isocyanates

Li‐Jun Xiao, Qi‐Lin Zhou, Yuqing Wang, Meng-Ying Qian
article en
6 citations

Abstract

The hydrocarbamoylation of alkenes with isocyanates is a promising method for synthesizing amides. However, applying this strategy to more inert, simple alkenes, such as styrenes, α-olefins, and internal alkenes, poses significant challenges. Here, we report the first nickel-catalyzed hydrocarbamoylation of alkenes with isocyanates, facilitated by triethoxysilane to reduce nickelacycle intermediates. By switching ligands─including 6,6'-dimethyl-2,2'-bipyridine and <i>N</i>-heterocyclic carbene─this method efficiently produces amides from a diverse array of alkenes, including styrenes, α-olefins, internal alkenes, and gaseous olefins.

Organic LettersVol. 27(12)
Nankai University (CN)
National Natural Science Foundation of China, National Key Research and Development Program of China, Fundamental Research Funds for the Central Universities
Clean water and sanitation
Openalex Percentile: Top 5%
Chemical Synthesis and Reactions
5.62
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