Synthesis
DOI: 10.1055/a-2640-2026
Paper

Ni-Catalyzed Regioselective Hydrodimerization of Enamides with Unactivated Alkenes

Qifa Chen
1   Center for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, Shanghai, China
2   Institute of Nanoscience and Engineering, Henan University, Kaifeng, China
,
Qing Yan
2   Institute of Nanoscience and Engineering, Henan University, Kaifeng, China
,
Li Cheng
1   Center for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, Shanghai, China
,
Yanhong Song
1   Center for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, Shanghai, China
,
1   Center for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, Shanghai, China
2   Institute of Nanoscience and Engineering, Henan University, Kaifeng, China
› Author Affiliations

Supported by: National Natural Science Foundation of China 22271182
The authors acknowledge the financial support of the National Natural Science Foundation of China (22271182).


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Abstract

In this study, we described the Ni-catalyzed cross-hydrodimerization of enamides with unactivated alkenes under SiH/DTBP-mediated thermoredox conditions that was promoted by catalytic CuBr. The reaction afforded α-branched primary amines/secondary amides in good yields and with high regioselectivity through the formation of a C(sp3)–C(sp3) bond at the N-α-carbons. Excellent functional compatibility was observed across a wide range of sterically congested enamides and alkenes, including allylic branched enamides and 1,1-disubstituted alkenes. The use of chiral BiOx ligand enabled the formation of chiral amides with a high level of enantioselectivity. The present study offers a new entry for expediting the preparation of secondary amides appended to internal alkyl chains, complementing existing methods in the rapidly growing field of C(sp3)–C(sp3) bond construction via the hydrodimerization of two distinct alkenes.

Supplementary Material



Publication History

Received: 15 May 2025

Accepted after revision: 19 June 2025

Accepted Manuscript online:
20 June 2025

Article published online:
04 August 2025

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