Ligands with 1,10-phenanthroline scaffold for highly regioselective iron-catalyzed alkene hydrosilylation

Meng-Yang Hu, Qiao He, Song-Jie Fan, Zi-Chen Wang, Luo-Yan Liu, Yi-Jiang Mu, Qian Peng () and Shou-Fei Zhu ()
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Meng-Yang Hu: State Key Laboratory and Institute of Elemento-Organic Chemistry
Qiao He: State Key Laboratory and Institute of Elemento-Organic Chemistry
Song-Jie Fan: State Key Laboratory and Institute of Elemento-Organic Chemistry
Zi-Chen Wang: State Key Laboratory and Institute of Elemento-Organic Chemistry
Luo-Yan Liu: State Key Laboratory and Institute of Elemento-Organic Chemistry
Yi-Jiang Mu: State Key Laboratory and Institute of Elemento-Organic Chemistry
Qian Peng: State Key Laboratory and Institute of Elemento-Organic Chemistry
Shou-Fei Zhu: State Key Laboratory and Institute of Elemento-Organic Chemistry

Nature Communications, 2018, vol. 9, issue 1, 1-11

Abstract: Abstract Transition-metal-catalyzed alkene hydrosilylation is one of the most important homogeneous catalytic reactions, and the development of methods that use base metals, especially iron, as catalysts for this transformation is a growing area of research. However, the limited number of ligand scaffolds applicable for base-metal-catalyzed alkene hydrosilylation has seriously hindered advances in this area. Herein, we report the use of 1,10-phenanthroline ligands in base-metal catalysts for alkene hydrosilylation. In particular, iron catalysts with 2,9-diaryl-1,10-phenanthroline ligands exhibit unexpected reactivity and selectivity for hydrosilylation of alkenes, including unique benzylic selectivity with internal alkenes, Markovnikov selectivity with terminal styrenes and 1,3-dienes, and excellent activity toward aliphatic terminal alkenes. According to the mechanistic studies, the unusual benzylic selectivity of this hydrosilylation initiates from π–π interaction between the phenyl of the alkene and the phenanthroline of the ligand. This ligand scaffold and its unique catalytic model will open possibilities for base-metal-catalyzed hydrosilylation reactions.

Date: 2018
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DOI: 10.1038/s41467-017-02472-6

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