Copper and Silver Acetylides in Organic Synthesis

Walter Reppe Revival – Identification and Genesis of Copper Acetylides Cu2C2 as Active Species in Ethynylation Reactions

“…The C 2 ‐unit is surrounded by four end‐on and four side‐on coordinated Cu atoms [13] . Several other polymer‐like structures of copper acetylides were published [3a,d,14] . A general formula is given in Scheme 2 for illustration.…”

Synthesis of 1,2,3-Triazoles from Alkyne-Azide Cycloaddition Catalyzed by a Bio-Reduced Alkynylcopper (I) Complex

“…In this regard, diverse copper catalysts have been designed, prepared and used in CuAAC reactions for several reaction conditions; among these catalysts alkynylcopper (I) complexes, namely copper acetylides, have been identified as efficient catalysts in these reactions [4]. Although first reports described that metal acetylides are explosives [5], recent reports show some stable copper acetylides with excellent catalytic properties in CuAAC reactions [6][7][8][9].…”

Stoichiometric and Structural Diversity of Silver Hydroxymethylacetylenide Coordination Polymers

“…[1][2][3][4] Their structures and chemical properties are well known, [5,6] and they have been widely used in organic chemistry for different applications. [7][8][9][10][11][12][13][14][15] A well-known diagnostic test with Ag + for the presence of the terminal acetylenic group that is based on the formation of a precipitate from an ammoniacal solution of silver nitrate, was used through mid-20th century. [16][17][18][19] Pure silver acetylide is a heat-and shock-sensitive high explosive despite the fact that it does not evolve any gas on ignition.…”

“…For example, 3‐ethoxyprop‐1‐ynyl silver and phenylethynyl silver were reported in 1865 and 1870 . Their structures and chemical properties are well known,, and they have been widely used in organic chemistry for different applications . A well‐known diagnostic test with Ag + for the presence of the terminal acetylenic group that is based on the formation of a precipitate from an ammoniacal solution of silver nitrate, was used through mid‐20th century .…”