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mild conditions and broad scope of the reaction enables quick
access to a large variety of chalcogenated enamides. Prelimina-
ry mechanistic studies support a proposed cationic pathway
via chalcogenium ion intermediates. To our knowledge, this
study provides the first example of intermolecular chalcogena-
tive amination of alkynes and represents a significant addition
to the limited intermolecular amino bisfunctionalization of al-
kynes. Mechanistic studies also provide valuable insights for
the development of highly selective aminative bisfunctionaliza-
tion of alkynes.
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Phenyl acetylene (1.0 equiv, 0.2 mmol, 22 mL) was added to a solu-
tion of NFSI (1.2 equiv, 0.24 mmol, 75.7 mg), and (PhSe)2 (1.2 equiv,
0.24 mmol, 75.3 mg) in CH2Cl2 (2 mL) in an oven-dried glass tube.
The reaction mixture was stirred at room temperature for 2 h
under an air atmosphere and was quenched by addition of water.
The mixture was extracted with CH2Cl2 (35 mL), and the com-
bined organic phases were dried over anhydrous Na2SO4. The sol-
vent was evaporated in vacuo, and the residue was purified by
column chromatography (hexane/ethyl acetate, 10:1 (v/v)) to give
the product 3a (100.4 mg, 90%).
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Acknowledgements
We gratefully acknowledge financial support from National
Natural Science Foundation of China (Nos. 21372041,
21402025) and the Fundamental Research Funds for the Cen-
tral Universities (2412015KJ014).
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Keywords: alkyne
selectivity
· amination · chalcogen · copper ·
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3517
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