TY - JOUR A1 - Ghosh, Sujit A1 - Biswas, Kinkar A1 - Bhattacharya, Suchandra A1 - Ghosh, Pranab A1 - Basu, Basudeb T1 - Effect of the ortho-hydroxy group of salicylaldehyde in the A3 coupling reaction: A metal-catalyst-free synthesis of propargylamine JF - Beilstein Journal of Organic Chemistry PY - 2017/// VL - 13 SP - 552 EP - 557 SN - 1860-5397 DO - 10.3762/bjoc.13.53 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.13.53 KW - A3 coupling KW - metal-catalyst-free KW - propargylamine KW - salicylaldehyde KW - terminal alkyne N2 - The synthesis of propargylamines via A3 coupling mostly under metal-catalyzed procedures is well known. This work invented an unprecedented effect of salicylaldehyde, one of the A3 coupling partners, which could lead to the formation of propargylamine, an important pharmaceutical building block, in the absence of any metal catalyst and under mild conditions. The role of the hydroxy group in ortho position of salicylaldehyde has been explored, which presumably activates the Csp–H bond of the terminal alkyne leading to the formation of propargylamines in good to excellent yields, thus negating the function of the metal catalyst. This observation is hitherto unknown, tested for a variety of salicylaldehyde, amine and acetylene, established as a general protocol, and is believed to be of interest for synthetic chemists from green chemistry. ER -