Silver-mediated C–H bond functionalization: one-pot to construct substituted indolizines from 2-alkylazaarenes with alkynes

Silver-catalysed reactions of alkynes: recent advances

“…77 Notably, the reaction of trimethylsilylacetylene and methyl 2-pyridylacetate resulted in the desiliconization product 65 0 in 55% yield. This reaction provides a straightforward route to access biologically important indolizines 65 (Scheme 29).…”

Highly efficient AgNO3‐catalyzed approach to 2‐(benzo[d]azol‐2‐yl)phenols from salicylaldehydes with 2‐aminothiophenol, 2‐aminophenol and benzene‐1,2‐diamine

“…Over the past decade, silver salt catalysts have significantly emerged to promote a broad range of organic transformations, such as cyclization, cycloaddition, allylation, tandem reactions, decarboxylation and other reactions owing to their efficiency, abundance, affordability and simple operation. Very recently, silver nitrate (AgNO 3 ) has attracted much attention as a promising alternative to traditional transition metal catalysts and has also been employed for organic reactions, such as phosphorylation, radical reactions, addition, domino reactions and others …”

Recent Organic Transformations with Silver Carbonate as a Key External Base and Oxidant

“…Here, the authors suggested a reaction mechanism based on the results of a deuterium-labeling experiment. In the case of a terminal alkyne (Scheme 22 (a)), silver acetylide 1-I was initially generated from alkyne 1 and Ag(I), and 2alkylazaarene In 2014, Pan and co-workers reported the construction of substituted indolizines via a Ag(I)-mediated C-H bond functionalization of 2-alkylazaarenes with alkynes (Scheme 21) [35]. We already discussed a Ag(I)-mediated synthesis of indolizines 12 from terminal alkynes 1 and pyridine derivatives 11 (Scheme 7), and the reaction was proposed to involve a 5-endo-dig cyclization between silver phenylacetylide and a chelated intermediate.…”