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Peer-reviewedCC BY 4.0Advanced Science

NiH‐Catalyzed Enantio‐ and Regioselective Hydroselenylation of Unactivated Alkenes

  • Hyung‐Joon Kang1,2
  • Jaehun Kim1,2
  • Sungwoo Hong1,2
  1. 1Center for Catalytic Hydrocarbon Functionalizations Institute for Basic Science (IBS) Daejeon Republic of Korea
  2. 2Department of Chemistry Korea Advanced Institute of Science and Technology (KAIST) Daejeon Republic of Korea
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Abstract

Chiral alkyl selenides are valuable motifs in medicinal chemistry and redox‐active molecular design, yet enantioselective hydroselenylation of unactivated alkenes remains challenging due to limited control over regio‐ and enantioselectivity. Here, we report nickel‐hydride‐catalyzed enantio‐ and regioselective hydroselenylation of unactivated alkenes directed by native amide groups using readily available diselenides. The method accommodates both terminal and internal alkenes as well as both aryl and alkyl diselenides, exhibiting broad functional‐group tolerance and delivering structurally diverse chiral aliphatic selenides with high regio‐ and enantioselectivity under mild conditions. Mechanistic studies support enantiodetermining hydronickelation followed by single‐electron diselenide activation and selective capture of the selenium radical by the chiral alkyl–nickel intermediate. This work establishes a general platform for asymmetric C─Se bond formation through the integration of NiH catalysis and radical selenium transfer.

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Cite

BibTeXRIS
BibTeX
@article{kang2026nihcatalyzed,
  title = {{NiH‐Catalyzed Enantio‐ and Regioselective Hydroselenylation of Unactivated Alkenes}},
  author = {Hyung‐Joon Kang and Jaehun Kim and Sungwoo Hong},
  journal = {Advanced Science},
  year = {2026},
  month = aug,
  doi = {10.1002/advs.77070},
  url = {https://doi.org/10.1002/advs.77070},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - NiH‐Catalyzed Enantio‐ and Regioselective Hydroselenylation of Unactivated Alkenes
AU  - Hyung‐Joon Kang
AU  - Jaehun Kim
AU  - Sungwoo Hong
PY  - 2026
DA  - 2026/08/11
JO  - Advanced Science
DO  - 10.1002/advs.77070
UR  - https://doi.org/10.1002/advs.77070
AB  - Chiral alkyl selenides are valuable motifs in medicinal chemistry and redox‐active molecular design, yet enantioselective hydroselenylation of unactivated alkenes remains challenging due to limited control over regio‐ and enantioselectivity. Here, we report nickel‐hydride‐catalyzed enantio‐ and regioselective hydroselenylation of unactivated alkenes directed by native amide groups using readily available diselenides. The method accommodates both terminal and internal alkenes as well as both aryl and alkyl diselenides, exhibiting broad functional‐group tolerance and delivering structurally diverse chiral aliphatic selenides with high regio‐ and enantioselectivity under mild conditions. Mechanistic studies support enantiodetermining hydronickelation followed by single‐electron diselenide activation and selective capture of the selenium radical by the chiral alkyl–nickel intermediate. This work establishes a general platform for asymmetric C─Se bond formation through the integration of NiH catalysis and radical selenium transfer.
SN  - 2198-3844
ER  -