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Ligand-promoted cobalt-catalyzed radical hydroamination of alkenes

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  • Xuzhong Shen

    (Zhejiang University)

  • Xu Chen

    (Zhejiang University)

  • Jieping Chen

    (Zhejiang University)

  • Yufeng Sun

    (Zhejiang University)

  • Zhaoyang Cheng

    (Zhejiang University)

  • Zhan Lu

    (Zhejiang University)

Abstract

Highly regio- and enantioselective intermolecular hydroamination of alkenes is a challenging process potentially leading to valuable chiral amines. Hydroamination of alkenes via metal-catalyzed hydrogen atom transfer (HAT) with good regioselectivity and functional group tolerance has been reported, however, high enantioselectivity has not been achieved due to the lack of suitable ligands. Here we report a ligand-promoted cobalt-catalyzed Markovnikov-type selective radical hydroamination of alkenes with diazo compounds. This operationally simple protocol uses unsymmetric NNN-tridentate (UNT) ligand, readily available alkenes and hydrosilanes to construct hydrazones with good functional group tolerance. The hydrazones can undergo nitrogen–nitrogen bond cleavage smoothly to deliver valuable amine derivatives. Additionally, asymmetric intermolecular hydroamination of unactivated aliphatic terminal alkenes using chiral N-imidazolinylphenyl 8-aminoquinoline (IPAQ) ligands has also been achieved to afford chiral amine derivatives with good enantioselectivities.

Suggested Citation

  • Xuzhong Shen & Xu Chen & Jieping Chen & Yufeng Sun & Zhaoyang Cheng & Zhan Lu, 2020. "Ligand-promoted cobalt-catalyzed radical hydroamination of alkenes," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-14459-x
    DOI: 10.1038/s41467-020-14459-x
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    Cited by:

    1. Qingyu Xing & Preeti P. Chandrachud & Khalilia Tillett & Justin M. Lopchuk, 2024. "Regioselective hydroamination of unactivated olefins with diazirines as a diversifiable nitrogen source," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    2. Yao Zhang & Deyong Qiao & Mei Duan & You Wang & Shaolin Zhu, 2022. "Enantioselective synthesis of α-aminoboronates by NiH-catalysed asymmetric hydroamidation of alkenyl boronates," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    3. Bin Cui & Yuting Zheng & Hui Sun & Huijian Shang & Man Du & Yuxuan Shang & Cafer T. Yavuz, 2024. "Catalytic enantioselective intramolecular hydroamination of alkenes using chiral aprotic cyclic urea ligand on manganese (II)," Nature Communications, Nature, vol. 15(1), pages 1-12, December.

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