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Catalyst-controlled regiodivergent ring-opening C(sp3)–Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis

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Abstract

A catalyst-controlled regiodivergent and stereospecific ring-opening C(sp3)–Si cross-coupling of 2-arylaziridines with silylborane enabled by synergistic Pd/Cu dual catalysis has been developed. Just by selecting a suitable combination of catalysts, the regioselectivity of the coupling is completely switched to efficiently provide two regioisomers of β-silylamines (i.e., β-silyl-α-phenethylamines and β-silyl-β-phenethylamines) in good to high yields. Furthermore, a slight modification of the reaction conditions caused a drastic change in reaction pathways, leading to a tandem reaction to produce another regioisomer of silylamine (i.e., α-silyl-β-phenethylamines) in an efficient and selective manner.

Graphical abstract: Catalyst-controlled regiodivergent ring-opening C(sp3)–Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis

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Publication details

The article was received on 23 May 2019, accepted on 30 Jul 2019 and first published on 31 Jul 2019


Article type: Edge Article
DOI: 10.1039/C9SC02507C
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY license
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    Catalyst-controlled regiodivergent ring-opening C(sp3)–Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis

    Y. Takeda, K. Shibuta, S. Aoki, N. Tohnai and S. Minakata, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC02507C

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