103-81-1Relevant articles and documents
Selective aerobic hydrolysis of nitriles to amides using cobalt(II)/zinc
Keshipour, Sajjad,Shaabani, Ahmad
, p. 5071 - 5078 (2015)
A novel protocol has been developed for the aerobic hydrolysis of nitriles to amides using cobalt(II)/zinc without using any strong acids and bases under solvent-free conditions. The reaction showed good performance for benzonitriles with sensitive groups such as ester and carboxylic acid.
Highly active, chemo- and enantioselective Pt-SPO catalytic systems for the synthesis of aromatic carboxamides
Gulyás, Henrik,Rivilla, Ivan,Curreli, Simona,Freixa, Zoraida,Van Leeuwen, Piet W. N. M.
, p. 3822 - 3828 (2015)
Platinum complexes modified with a chiral non-racemizing SPO preligand 1 have been applied in the hydration of aromatic nitriles. [Pt(1)3Cl]Cl formed readily from Pt(COD)Cl2. The chiral secondary phosphine oxide complex showed moderate activity in the hydration of para- and meta-substituted benzonitriles, but failed in converting the ortho-substituted derivatives. The hydride complex PtH(PR2OH)(PR2O-H?OR2P) (PR2OH = 1) formed from Pt(PPh3)4 and 1, and the cationic complex derived from [Pt(1)3Cl]Cl via direct chloride abstraction with AgNO3 were proven to be considerably more active, allowing us to extend the scope to the hydration of ortho-substituted aromatic nitriles, including axially chiral [1,1′-binaphthalene]-2,2′-dicarbonitrile. In the hydration of the racemic dinitrile, successful kinetic resolution has been achieved. The catalysts derived from non-racemizing 1 are the first chiral transition metal-SPO complexes that provide kinetic resolution in the hydration of a racemic chiral nitrile.
Light-induced hydrolysis of nitriles by photoproduced α-MnO 2 nanorods on polystyrene beads
Jana, Subhra,Praharaj, Snigdhamayee,Panigrahi, Sudipa,Basu, Soumen,Pande, Surojit,Chang, Chien-Hsiang,Pal, Tarasankar
, p. 2191 - 2193 (2007)
A green chemistry approach has been furnished for photochemical deposition of α-MnO2 nanorods onto the surface of functionalized polystyrene beads through immobilization of MnO+4- in alkaline condition under visible light. Then the composite material was exploited as a fruitful and novel solid-phase catalyst for the one-step and facile synthesis of amide compounds from nitriles under visible light in weakly basic medium.
Simple and efficient cleavage of the N-(1-phenylethyl) unit of carboxamides with methanesulfonic acid
Paik, Seunguk,Lee, Jun Young
, p. 1813 - 1815 (2006)
Cleavage of the N-(1-phenylethyl) unit of carboxamides using less than 1 equiv of MsOH in refluxing toluene was found to be simple and very efficient leading to the desired amides in good to excellent yields, and also proved to be more effective compared with reductive methods using hydrogen sources, or acid hydrolysis reagents such as TFA and TsOH. The method selectively cleaved only the N-(1-phenylethyl) group of N-benzyl-N-(1-phenylethyl)amides.
Choline chloride based eutectic solvent: An efficient and reusable solvent system for the synthesis of primary amides from aldehydes and from nitriles
Patil, Umakant B.,Singh, Abhilash S.,Nagarkar, Jayashree M.
, p. 1102 - 1106 (2014)
Choline chloride: a 2ZnCl2 based deep eutectic solvent was found to be a simple, green, efficient and new solvent system for the preparation of primary amides from aldehydes. The same catalytic system is also applicable for the preparation of amides from nitriles. Good to excellent yields of primary amides were obtained in both these transformations.
Transition metal-free sodium borohydride promoted controlled hydration of nitriles to amides
Verma, Praveen Kumar,Kumar, Neeraj,Sharma, Upendra,Bala, Manju,Kumar, Vishal,Singh, Bikram
, p. 2867 - 2875 (2013)
A transition metal-free process, promoted by sodium borohydride, has been developed for convenient and selective hydration of nitriles to corresponding amides. The present process converts the aromatic, aliphatic, and heteroaromatic nitriles with wide functional group tolerance. The regioselective hydration of one nitrile moiety in the presence of an other nitrile group makes high impact in the present protocol.
Visible Light-Induced Iodine-Catalyzed Transformation of Terminal Alkynes to Primary Amides via C≡C Bond Cleavage under Aqueous Conditions
Dighe, Shashikant U.,Batra, Sanjay
, p. 500 - 505 (2016)
The visible light-induced iodine-catalyzed oxidative cleavage of the C≡C bond for transforming terminal alkynes into primary amides in the presence of ammonia under aqueous conditions is described. This metal-free protocol which ensued via initial hydroamination of the acetylene bond followed by liberation of diiodomethane (CH2I2) was found to be applicable to aromatic, heteroaromatic and aliphatic alkynes.
Catalytic Hydration of Nitriles to Amides with Manganese Dioxide on Silica Gel
Liu, Kwang-Ting,Shih, Mei-Hsiu,Huang, Hsiau-Wen,Hu, Chia-Juei
, p. 715 - 717 (1988)
Hydration of representative nitriles with silica gel supported manganese dioxide at the reflux temperature of hydrocarbon solvents gives the corresponding amides in good to excellent yield.Phenylacetonitrile, however, was partially oxidized to benzoylformamide.Other manganese catalyst systems were also evaluated.
Trash to treasure: Eco-friendly and practical synthesis of amides by nitriles hydrolysis in WepPA
Sun, Yajun,Jin, Weiwei,Liu, Chenjiang
, (2019)
The hydration of nitriles to amides in a water extract of pomelo peel ash (WEPPA) was realized with moderate to excellent yields without using external transition metals, bases or organic solvents. This reaction features a broad substrate scope, wide functional group tolerance, prominent chemoselectivity, and good reusability. Notably, a magnification experiment in this bio-based solvent at 100 mmol further demonstrated its practicability.
Selective hydration of nitriles to amides promoted by an Os-NHC catalyst: Formation and X-ray characterization of κ2-amidate intermediates
Buil, Maria L.,Cadierno, Victorio,Esteruelas, Miguel A.,Gimeno, Jose,Herrero, Juana,Izquierdo, Susana,Onate, Enrique
, p. 6861 - 6867 (2012)
The complex [Os(η6-p-cymene)(OH)IPr]OTf (1; IPr = 1,3-bis(2,6-diisopropylphenyl)imidazolylidene; OTf = CF3SO 3) reacts with benzonitrile and acetonitrile to afford the κ2-amidate derivatives [Os(η6-p-cymene) {κ2O,N-NHC(O)R}IPr]OTf (R = Ph (2), CH3 (3)). Their formation has been investigated by DFT calculations (B3PWP1), starting from the model intermediate [Os(η6-benzene)(OH)(CH3CN)IMe] + (IMe = 1,3-bis(2,6-dimethylphenyl)imidazolylidene). Complex 2 has been characterized by X-ray diffraction analysis. In the presence of water, the κ2-amidate species release the corresponding amides and regenerate 1. In agreement with this, complex 1 has been found to be an efficient catalyst for the selective hydration of a wide range of aromatic and aliphatic nitriles to amides, including substituted benzonitriles, cyanopyridines, acetonitrile, and 2-(4-isobutylphenyl)propionitrile among others. The mechanism of the catalysis is also discussed.
