1122-56-1Relevant articles and documents
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Gipson,R.M. et al.
, p. 1425 - 1426 (1963)
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Kornblum,N.,Singaram,S.
, p. 4727 - 4729 (1979)
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Raber et al.
, p. 7671 (1977)
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RhI-catalyzed hydration of organonitriles under ambient conditions
Goto, Akihiro,Endo, Kohei,Saito, Susumu
, p. 3607 - 3609 (2008)
(Chemical Presented) New scoop on scope and selectivity: The hydration of organonitriles catalyzed by a RhI(OMe) species under nearly pH-neutral and ambient conditions (25°C, 1 atm) is chemoselective and high-yielding (93 to 99%), has a broad substrate scope, and may thus be complementary to enzymatic hydration methods for the introduction of a terminal amido group (CONH2) onto a carbon chain.
An environmentally benign electrochemical process for the reduction of carboxylic acid hydrazides to amides
Mentel, Matthias,Beier, Matthias J.,Breinbauer, Rolf
, p. 1463 - 1468 (2009)
The transformation of acid hydrazides to primary amides is of certain relevance for the organic synthesis of complex molecules. While existing methods require harsh reaction conditions, we present an electrochemical approach in which monoacylhydrazines are reduced to primary amides in 40-90% yield in a divided electrochemical cell with a tin cathode. This method proved superior to reduction by sodium/mercury or lithium/biphenyl in terms of yield and practicability. Most importantly, the new method is distinguished by its tolerance of aryl halogen and olefinic groups. Georg Thieme Verlag Stuttgart.
Investigation of binap-based hydroxyphosphine arene-ruthenium(II) complexes as catalysts for nitrile hydration
Toms-Mendivil, Eder,Menndez-Rodrguez, Luca,Francos, Javier,Crochet, Pascale,Cadierno, Victorio
, p. 63466 - 63474 (2014)
The binap-based hydroxyphosphine-(η6-arene)-ruthenium(ii) complexes [RuX{η6:κ1(P)-PPh2-binaphthyl}{PPh2(OH)}][OTf] (X = OTf (4), Cl (5)) have been evaluated as potential catalysts for the selective hydration of nitriles to primary amides. The triflate derivative 4 proved to be the most active, being able to hydrate a large variety of aromatic, heteroaromatic, α,β-unsaturated and aliphatic nitriles in pure water at 100°C. The utility of complex 4 to promote the catalytic rearrangement of aldoximes has also been demonstrated. In addition, insights about the role played by the hydroxyphosphine ligand PPh2(OH) during the catalytic reactions are given.
Development of a Scalable Synthesis of trans-4-Fluorocyclohexylamine via Directed Hydrogenation
Leung, Joyce C.,Nguyen, Thach T.,Krawiec, Mariusz,Gao, Donghong A.,Reeves, Jonathan T.
, p. 632 - 641 (2020/12/22)
Herein, a scalable and practical process to prepare trans-4-fluorocyclohexylamine hydrochloride (1a) is described. By exploitation of the embedded gem-difluoride motif in the commercially available 4,4-difluorocyclohexanecarboxylic acid, a derived orthoester-masked acid underwent dehydrofluorination to provide the requisite vinyl fluoride for a directed hydrogenation event, enabling selective access to the trans-configuration of 1a.
Mechanochemical Synthesis of Primary Amides
Gómez-Carpintero, Jorge,Sánchez, J. Domingo,González, J. Francisco,Menéndez, J. Carlos
, p. 14232 - 14237 (2021/10/20)
Ball milling of aromatic, heteroaromatic, vinylic, and aliphatic esters with ethanol and calcium nitride afforded the corresponding primary amides in a transformation that was compatible with a variety of functional groups and maintained the integrity of a stereocenter α to carbonyl. This methodology was applied to α-amino esters and N-BOC dipeptide esters and also to the synthesis of rufinamide, an antiepileptic drug.
Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups
Govindan, Karthick,Chen, Nian-Qi,Chuang, Yu-Wei,Lin, Wei-Yu
supporting information, p. 9419 - 9424 (2021/11/30)
We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.
