Nickel-Catalyzed 3,2-Hydroallylation of 1,1-Disubstituted Allenes with Vinyl Cyclopropanes: Access to Functionalized 1,4-Dienes

A Ni(II)-catalyzed regioselective 3,2-hydroallylation of 1,1-disubstituted allenes has been developed using vinyl cyclopropanes as allyl precursors, providing efficient access to highly functionalized 1,4-dienes. The presence of a carbonyl functionality in the cyclopropane substrate enables a modified 1,6-type nucleophilic addition pathway via ring opening. A tailored N<sup>∧</sup>N-type ligand was found to be essential for promoting the transformation under NiH catalysis.

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Publication Details

Journal
Organic Letters
Published
2025-11-08
DOI
https://doi.org/10.1021/acs.orglett.5c04270
Citations
1
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.94
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article

Nickel-Catalyzed 3,2-Hydroallylation of 1,1-Disubstituted Allenes with Vinyl Cyclopropanes: Access to Functionalized 1,4-Dienes

Ujjwal Karmakar, Eun Jin Cho, Haeryeong Jeong
1 citations
Organic Letters
Catalytic C–H Functionalization Methods
0.94
article

Nickel-Catalyzed 3,2-Hydroallylation of 1,1-Disubstituted Allenes with Vinyl Cyclopropanes: Access to Functionalized 1,4-Dienes

Ujjwal Karmakar, Eun Jin Cho, Haeryeong Jeong
article en
1 citations

Abstract

A Ni(II)-catalyzed regioselective 3,2-hydroallylation of 1,1-disubstituted allenes has been developed using vinyl cyclopropanes as allyl precursors, providing efficient access to highly functionalized 1,4-dienes. The presence of a carbonyl functionality in the cyclopropane substrate enables a modified 1,6-type nucleophilic addition pathway via ring opening. A tailored N<sup>∧</sup>N-type ligand was found to be essential for promoting the transformation under NiH catalysis.

Organic LettersVol. 27(46)
Chung-Ang University (KR)
Openalex Percentile: Top 20%
Catalytic C–H Functionalization Methods
0.94
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