Journal
CHEMICAL SCIENCE
Volume 10, Issue 37, Pages 8642-8647Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc02507c
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Funding
- [JP16H01023]
- [JP19H04580]
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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 beta-silylamines (i.e., beta-silyl-alpha-phenethylamines and beta-silyl-beta-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., alpha-silyl-beta-phenethylamines) in an efficient and selective manner.
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