Gold-catalyzed 1,2-difunctionalizations of aminoalkynes using only N- and O-containing oxidants |
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Authors: | Mukherjee Anupam Dateer Ramesh B Chaudhuri Rupsha Bhunia Sabyasachi Karad Somnath Narayan Liu Rai-Shung |
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Affiliation: | Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan 30043, ROC. |
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Abstract: | We report two viable routes for the 1,2-difunctionalization of aminoalkynes using only oxidants. In the presence of a gold catalyst, nitrones enable the oxoamination of aminoalkynes 1 to form 2-aminoamides 2. With a suitable gold catalyst, nitrosobenzenes implement an alkyne/nitroso metathesis of the same substrates to give 2-oxoiminylamides 3. These two novel oxidations also provide 1,2-aminoalcohols with opposite regioselectivity via NaBH(4) reduction in situ. |
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