Gold-catalyzed 1,2-difunctionalizations of aminoalkynes using only N- and O-containing oxidants

Anupam Mukherjee; Ramesh B Dateer; Rupsha Chaudhuri; Sabyasachi Bhunia; Somnath Narayan Karad; Rai-Shung Liu

doi:10.1021/ja208150d

Gold-catalyzed 1,2-difunctionalizations of aminoalkynes using only N- and O-containing oxidants

J Am Chem Soc. 2011 Oct 5;133(39):15372-5. doi: 10.1021/ja208150d. Epub 2011 Sep 12.

Authors

Anupam Mukherjee¹, Ramesh B Dateer, Rupsha Chaudhuri, Sabyasachi Bhunia, Somnath Narayan Karad, Rai-Shung Liu

Affiliation

¹ Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan 30043, ROC.

PMID: 21905664
DOI: 10.1021/ja208150d

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.