1007597-80-9Relevant academic research and scientific papers
Copper(I)-catalyzed highly regio- and stereoselective boron addition-protonolysis of alkynamides to give alkenamides
He, Guangke,Zhang, Qijun,Huang, Hai,Chen, Shan,Wang, Qiang,Zhang, Dongming,Zhang, Rong,Zhu, Hongjun
, p. 6979 - 6989 (2013)
Copper-catalyzed and highly chemoselective reduction of N-alkynylamides by a boron addition-protonolysis protocol is presented. The reaction proceeds with the addition of boryl-copper complex to N-alkynylamides with high regioselectivity and stereoselectivity, followed by regiocontrolled transmetallation of the α-site of the alkenylboronate with MeOCuL to afford N-alkenylamides in good yields. Deuterium labeling experiments indicated that both of the alkenyl hydrogen atoms originate from the additive methanol. The copper-catalyzed semireduction of N-alkynylamides by a boron addition-protonlysis protocol afforded N-alkenylamides in good yields with high stereo- and chemoselectivity. Deuterium labeling experiments indicated that both of the alkenyl hydrogen atoms of the N-alkenylamides originate from the additive methanol. Copyright
Aerobic oxidative alkynylation of H-phosphonates and amides: An efficient route for the synthesis of alkynylphosphonates and ynamides using a recyclable Cu-MnO catalyst
Singh, Harshvardhan,Sahoo, Tapan,Sen, Chiranjit,Galani, Sunil M.,Ghosh, Subhash Chandra
, p. 1691 - 1698 (2019/04/08)
An atom-economical and efficient route for the synthesis of alkynylphosphonates and ynamides by aerobic oxidative alkynylation of H-phosphonates and amides with both aliphatic and aromatic alkynes using our synthesized recyclable heterogeneous Cu-MnO catalyst has been developed. The phosphorylation was carried out under base- and ligand-free conditions, and in the presence of air as the sole oxidant. The reaction is compatible with a wide variety of functional groups and generates alkynylphosphonate and ynamide products in good to excellent yields. Both reactions can be scaled up to the gram scale without any decrease in the reaction yield and the reaction time is less compared to literature reports. The catalyst is recyclable and reused several times without any significant loss of reactivity.
Access to ynamides via CuO-mediated oxidative amidation of alkynes
Tong, Xiaogang,Ni, Guanghui,Deng, Xu,Xia, Chengfeng
supporting information, p. 2497 - 2500,4 (2012/12/12)
Copper(II) oxide mediated the direct coupling of terminal alkynes and amides by way of C-H functionalization to afford ynamides as useful building blocks. Some alkali halides such as KCl were discovered to play a key role as additive in the coupling react
Copper-catalyzed aerobic oxidative amidation of terminal alkynes: Efficient synthesis of ynamides
Hamada, Tetsuya,Ye, Xuan,Stahl, Shannon S.
, p. 833 - 835 (2008/09/21)
A copper-catalyzed method for the preparation of ynamides has been identified that proceeds via aerobic oxidative coupling of terminal alkynes with various nitrogen nucleophiles, including cyclic carbamates, amides and ureas, and N-alkyl-arylsulfonamides and indoles. Copyright
