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Nickel-Catalyzed Regioselective Hydrosilylation of Conjugated Dienes
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  • Xiaoyu Wu,
  • Wei Liu,
  • Liqun Yang,
  • Yue Wang,
  • Tianwen Liu,
  • Yao Yuan,
  • Yan Lu,
  • Zhaoguo Zhang
Xiaoyu Wu
Shanghai Jiao Tong University
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Wei Liu
Shanghai Jiao Tong University
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Liqun Yang
Shanghai Jiao Tong University
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Yue Wang
Shanghai Jiao Tong University
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Tianwen Liu
The University of Edinburgh
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Yao Yuan
Shanghai Jiao Tong University
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Yan Lu
Shanghai Jiao Tong University
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Zhaoguo Zhang
Shanghai Jiao Tong University

Corresponding Author:zhaoguo@sjtu.edu.cn

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Abstract

With the increasing demand for homoallylic silanes and allylic silanes, the highly efficient and regioselective hydrosilylations of conjugated dienes are urgently needed. Herein, we developed a Ni-catalyzed regiodivergent hydrosilylation of aromatic conjugated dienes by adjusting the temperature and ligands. Under low temperature (-30 oC), an eternal-ligand-free system (Ni/t-BuOK) can efficiently facili-tate the 3,4-anti-Markovnikov hydrosilylation to provide homoallylic silanes via electrophilic activation process; under room temperature (25 oC), a ligand-controlled system (Ni/t-BuOK/PPh3) can eventuate the 3,4-Markovnikov hydrosilylation to produce allylic silanes via Chalk-Harrod process. Both systems are compatible with various conjugated dienes and primary silanes in excellent yields and regioselec-tivities.
17 Aug 20231st Revision Received
18 Aug 2023Submission Checks Completed
18 Aug 2023Assigned to Editor
18 Aug 2023Review(s) Completed, Editorial Evaluation Pending
18 Aug 2023Reviewer(s) Assigned
21 Aug 2023Editorial Decision: Accept