2510-55-6Relevant articles and documents
Bengelmans et al.
, p. 885 (1977)
Kinetic Analysis of Aromatic Photocyanation: Naphthalene, Biphenyl, and Phenanthrene
Lemmetyinen, Helge J.
, p. 1269 - 1274 (1983)
Nucleophilic photocyanation of the unsubstituted aromatic hydrocarbons, naphthalene, biphenyl, and phenanthrene, in both dry and aqueous acetonitrile can be described by a mechanism involving two photoinduced transients.The primary step of the mechanism is the formation of a transient ionic complex through triplet excimer of aromatic hydrocarbon or, when an electron acceptor is present, through triplet exciplex.The attack of cyanide ion on the transient complex yields the cyanated radical, ArHCN., which in aqueous acetonitrile reacts with itself to yield cyano- and dihydrocyano-products or, in dry acetonitrile after being attacked by an electron, is oxidized to the cyano-product.The rate constants for the formation of radical ions and the attack of cyanide ion are calculated from the experimental results.
Cyanide-Free Cyanation of Aryl Iodides with Nitromethane by Using an Amphiphilic Polymer-Supported Palladium Catalyst
Niimi, Ryoko,Suzuka, Toshimasa,Uozumi, Yasuhiro
supporting information, p. 40 - 44 (2021/11/30)
A cyanide-free aromatic cyanation was developed that uses nitromethane as a cyanide source in water with an amphiphilic polystyrene poly(ethylene glycol) resin-supported palladium catalyst and an alkyl halide (1-iodobutane). The cyanation proceeds through the palladium-catalyzed cross-coupling of an aryl halide with nitromethane, followed by transformation of the resultant (nitromethyl)arene intermediate into a nitrile by 1-iodobutane.
Difluorocarbene-Based Cyanation of Aryl Iodides
Cao, Yu-Cai,Du, Ruo-Bing,Fu, Zhi-Hong,Guo, Yu,Lin, Jin-Hong,Xiao, Ji-Chang,Xiao, Xuan,Yao, Xu,Zhang, Yin-Xiang,Zheng, Xing
supporting information, p. 713 - 717 (2020/04/08)
A large number of efficient cyanation methods have been developed because of the wide range of applications of nitriles, but conventional methods usually suffer from the need for a toxic cyanation reagent. Although difluorocarbene chemistry has received increasing attention, the use of difluorocarbene as a sources of the nitrile carbon for nitrile groups remains largely unexplored. We describe a difluorocarbene-based cyanation of aryl iodides promoted by a cheap copper source, Cu(NO 3) 2 ·2.5H 2 O, under an air atmosphere. Ph 3 P + CF 2 CO 2-, an easily available and shelf-stable difluorocarbene reagent, and NaNH 2 are used as the carbon source and the nitrogen source for the nitrile group, respectively. The cyanation protocol is attractive because no toxic reagent is used and performing the reactions under an air atmosphere is operationally convenient.
