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

A catalyst-controlled regiodivergent and stereospecific ring-opening C(sp(3))–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 complete...

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Detalles Bibliográficos
Autores principales: Takeda, Youhei, Shibuta, Kaoru, Aoki, Shohei, Tohnai, Norimitsu, Minakata, Satoshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6844297/
https://www.ncbi.nlm.nih.gov/pubmed/31803438
http://dx.doi.org/10.1039/c9sc02507c
Descripción
Sumario:A catalyst-controlled regiodivergent and stereospecific ring-opening C(sp(3))–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.