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Issue 37, 2019
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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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Supplementary files

Article information


Submitted
23 May 2019
Accepted
30 Jul 2019
First published
31 Jul 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 8642-8647
Article type
Edge Article

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, 10, 8642
DOI: 10.1039/C9SC02507C

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