Fluoranthen und seine Derivate. III. Mitteilung

Improving palladium-catalyzed cyanation of aryl halides: development of a state-of-the-art methodology using potassium hexacyanoferrate(II) as cyanating agent

“…Most often they have been synthesized by the Rosenmund-von Braun reaction [15][16][17][18][19] from aryl halides or diazotization of anilines and subsequent Sandmeyer reaction [20][21][22] on laboratory as well as on industrial scale. Drawbacks of the Rosenmund-von Braun and the Sandmeyer reaction are the high temperature (150-250°C) and the use of stoichiometric amounts of copper(I) cyanide as cyanating agent, which leads to equimolar amounts of heavy metal waste.…”

Synthesis of [14C] labeled 2‐methoxypyrimidine‐5‐carboxylic acid

“…3 Aryl nitriles have been prepared by cyanation of iodides or bromides using CuCN or KCN in absence of solvent or in solvents like pyridine, quinoline, DMF, NMP at elevated temperature. [4][5][6][7][8][9][10][11] Under Von Braun conditions the reaction of 5-bromo-2-methoxypyrimidine with [ 14 C] CuCN in DMF at 1451C for 48 h did not yield cyano derivative.…”

Copper-catalyzed, oxidative sp2 C-H cyanation: facile synthesis of aromatic carbonitriles

“…Moreover, the nitrile moiety also serves as a key role during the transformations into the formation of amines, amides, acids/ester, ketones, aldehydes and heterocycles. 1 Typical strategies for the synthesis of aryl nitriles involve the Rosenmund-von Braun, [2][3] Sandmeyer, 4 and Schmidt 5 reactions. Recent advances show that the cross-coupling between aryl (pseudo)halides and various cyanide sources such as NaCN, 6 KCN, 7 CuCN, 8 TMSCN, 9 Zn(CN) 2 and acetone cyanohydrin 18 is also an alternative way to aryl nitriles.…”