Hydroaminoalkylation of 1,3-dienes by dual photoredox and nickel catalysis

A dual nickel/photoredox catalyzed hydroaminoalkylation of 1,3-dienes is presented. In this atom-economic and energetic protocol, the bulk industrial raw material isoprene and its derivatives are employed as allylic electrophile surrogates, which undergo a coupling with photoredox-generated α-amino alkyl radical species to produce valuable homoallylic amines efficiently. Preliminary mechanism experiments support the intervention of Ni-hydride species that undergo diene insertion to form Ni-allyl intermediates.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc03221k
Citations
1
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.94

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Hydroaminoalkylation of 1,3-dienes by dual photoredox and nickel catalysis

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1 citations
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Radical Photochemical Reactions
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article

Hydroaminoalkylation of 1,3-dienes by dual photoredox and nickel catalysis

Enhui Zhou, Lei Shi, Yuqing Chen, Jing‐Ran Shan, Heyang Xu, Lu Qiu, F.N. Jin
article en
1 citations

Abstract

A dual nickel/photoredox catalyzed hydroaminoalkylation of 1,3-dienes is presented. In this atom-economic and energetic protocol, the bulk industrial raw material isoprene and its derivatives are employed as allylic electrophile surrogates, which undergo a coupling with photoredox-generated α-amino alkyl radical species to produce valuable homoallylic amines efficiently. Preliminary mechanism experiments support the intervention of Ni-hydride species that undergo diene insertion to form Ni-allyl intermediates.

Chemical CommunicationsVol. 61(72)
University of California, Los Angeles (US), Dalian University of Technology (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 23%
Radical Photochemical Reactions
0.94
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