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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.

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 ?-silylamines (i.e., ?-silyl-?-phenethylamines and ?-silyl-?-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., ?-silyl-?-phenethylamines) in an efficient and selective manner.

SUBMITTER: Takeda Y 

PROVIDER: S-EPMC6844297 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Catalyst-controlled regiodivergent ring-opening C(sp<sup>3</sup>)-Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis.

Takeda Youhei Y   Shibuta Kaoru K   Aoki Shohei S   Tohnai Norimitsu N   Minakata Satoshi S  

Chemical science 20190731 37

A catalyst-controlled regiodivergent and stereospecific ring-opening C(sp<sup>3</sup>)-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>i.e.</i>, β-silyl-α-phenethylamines and β-silyl-β-phenethylamines) in good to high yields. Furthermore, a slight modif  ...[more]

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