Synthesis of<i>N</i>,<i>N</i>-Disubstituted 3-Amino-1,4-diynes and 3-Amino-1-ynes by Addition of Alkynyldimethylaluminum Reagents to<i>N</i>,<i>N</i>-Disubstituted Formamides and N,O-Acetals
作者:Balaji L. Korbad、Sang-Hyeup Lee
DOI:10.1002/ejoc.201402464
日期:2014.8
A range of alkynyldimethylaluminum reagents were added to N,N‐disubstituted formamides and the their acetals to provide the corresponding N,N‐disubstituted 3‐amino‐1,4‐diynes. Also, these reagents smoothly underwent the addition to N,O‐acetals to give the corresponding N,N‐disubstituted 3‐amino‐1‐ynes.
The synthesis of 3-amino-1,4-diynes has been developed by the two-component coupling of N,N-dimethyl formamide dimethyl acetal with terminal alkynes using CuO nanoparticles as an efficient catalyst under mild reaction conditions in ambient air. The procedure is applicable to aryl, alkyl, alkenyl, and heteroaryl alkynes. The CuO nanoparticles are easily recyclable without the loss of significant catalytic