Nickel-Catalyzed Regioselective Hydrosilylation of Conjugated Dienes†
Xiaoyu Wu
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China
Search for more papers by this authorWei Liu
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China
Search for more papers by this authorLiqun Yang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China
Search for more papers by this authorYue Wang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China
Search for more papers by this authorTianwen Liu
Joseph Black Building, The University of Edinburgh, David Brewster Road, Edinburgh, EH9 3FJ UK
Search for more papers by this authorYao Yuan
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China
Search for more papers by this authorYan Lu
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China
Search for more papers by this authorCorresponding Author
Zhaoguo Zhang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China
E-mail: [email protected]Search for more papers by this authorXiaoyu Wu
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China
Search for more papers by this authorWei Liu
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China
Search for more papers by this authorLiqun Yang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China
Search for more papers by this authorYue Wang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China
Search for more papers by this authorTianwen Liu
Joseph Black Building, The University of Edinburgh, David Brewster Road, Edinburgh, EH9 3FJ UK
Search for more papers by this authorYao Yuan
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China
Search for more papers by this authorYan Lu
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China
Search for more papers by this authorCorresponding Author
Zhaoguo Zhang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China
E-mail: [email protected]Search for more papers by this authorDedicated to the Memory of Professor Xiyan Lu.
Comprehensive Summary
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 °C), an eternal-ligand-free system (Ni/t-BuOK) can efficiently facilitate the 3,4-anti-Markovnikov hydrosilylation to provide homoallylic silanes via electrophilic activation process; under room temperature (25 °C), 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 regioselectivities.
Supporting Information
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Appendix S1: Supporting Information |
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