10.1002/asia.201900170
Chemistry - An Asian Journal
FULL PAPER
Conclusions
We gratefully acknowledge the Natural Science Foundation of
China (No.21606201) and the National Natural Science
Foundation of Zhejiang (No. LY13B020016) for financial support.
In summary, a novel single step method to obtain vicinal amines
by direct diamination reaction from accessible amines and α, β-
unsaturated ketones we have achieved. Chalcones and
secondary amines provided anticipated products in good to
excellent yields. The method obviated the need of metal catalyst
or hypervalent iodine reagents and proceeded well under mild
conditions, ready accessibility of the starting materials, simple
operation and good to high yields characterize the present
transformation. The investigation of diamination of alkene is still
ongoing.
Keywords: iodine • diamination • α, β- diamido ketone • C-N
bond • metal-free
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Experimental Section
General Information Unless otherwise noted, all commercial
reagents and solvents were obtained from the commercial
1
provider and used without further purification. H NMR spectra
were recorded on an NMR instrument operated at 500 MHz.
Chemical shifts are reported in prats per million with the solvent
resonance as the internal standard (CDCl3, δ 7.26). 13C NMR
spectra were recorded on an NMR instrument operated at 125
MHz with complete proton decoupling. Chemical shifts are
reported in parts per million with the solvent resonance as the
internal standard (CDCl3, δ 77.1). HRMS were recorded on a
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General Procedure for the Synthesis of 3. A mixtue of
chalcone (1a, 83.2 mg, 0.4 mmol), morpholine (2a, 105.0 mg,
1.2 mmol), K2CO3 (64.8 mg, 0.6 mmol), and iodine (101.6 mg,
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washed with water and the combined organic layers were
washed with brine and aqueous Na2S2O3, dried over anhydrous
Na2SO4, and concentrated in vacuo. Purification of the crude
product by flash chromatography on silica gel (eluent ethyl
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a white solid (127.8 mg, 84% yield).
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