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Rhodium-catalysed direct hydroarylation of alkenes and alkynes with phosphines through phosphorous-assisted C−H activation

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  • Dingyi Wang

    (Nanjing University)

  • Ben Dong

    (Nanjing University)

  • Yandong Wang

    (Nanjing University)

  • Jiasheng Qian

    (Nanjing University)

  • Jinjun Zhu

    (Nanjing University)

  • Yue Zhao

    (Nanjing University)

  • Zhuangzhi Shi

    (Nanjing University)

Abstract

Biarylphosphines have been widely applied as ligands in various synthetic methods, especially in transition-metal-catalysed carbon-carbon and carbon-heteroatom bond cross-coupling reactions. Based on the outstanding properties of the parent scaffolds, a general method for in situ modification of the commercial tertiary phosphine ligands to access a series of ligands is in high demand. Here we show that a rhodium-catalysed system is introduced for the hydroarylation of alkenes and alkynes with tertiary phosphines through P(III)-chelation assisted C-H activation. A series of ligand libraries containing alkyl and alkenyl substituted groups with different steric and electronic properties are obtained in high yields. Furthermore, several experimental studies are performed to uncover the key mechanistic features of the linear-selective hydroarylation of alkenes and branch-selective hydroarylation of alkynes.

Suggested Citation

  • Dingyi Wang & Ben Dong & Yandong Wang & Jiasheng Qian & Jinjun Zhu & Yue Zhao & Zhuangzhi Shi, 2019. "Rhodium-catalysed direct hydroarylation of alkenes and alkynes with phosphines through phosphorous-assisted C−H activation," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-11420-5
    DOI: 10.1038/s41467-019-11420-5
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    Cited by:

    1. Shao-Long Qi & Yu-Peng Liu & Yi Li & Yu-Xin Luan & Mengchun Ye, 2022. "Ni-catalyzed hydroarylation of alkynes with unactivated β-C(sp2)−H bonds," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    2. Dingyi Wang & Mingjie Li & Chengdong Shuang & Yong Liang & Yue Zhao & Minyan Wang & Zhuangzhi Shi, 2022. "Rhodium-catalyzed selective direct arylation of phosphines with aryl bromides," Nature Communications, Nature, vol. 13(1), pages 1-10, December.

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