Iodine-catalyzed one-pot synthesis of amides from nitriles via Ritter reaction

Theerthagiri, Palani; Lalitha, Appaswami; Arunachalam, Pirama Nayagam

doi:10.1016/j.tetlet.2010.03.057

Cited by 65 publications

(33 citation statements)

References 31 publications

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“…[17] Recently, the conversions of primary and secondary benzylic alcohols by FeA C H T U N G T R E N N U N G (III)-montmorillonite K10, [18] iron trichloride [19] and iodine [20] catalysts were reported. In addition, the Ritter reaction involving the activated tert-butyl acetate has been reported to be catalysed by sulfuric acid [21] or bismuth triflate.…”

Section: Resultsmentioning

confidence: 99%

Gold Catalysis: Alkyl Migration in the Addition of Alcohols to Nitriles

Ibrahim¹,

Hashmi

Röminger

2011

Adv Synth Catal

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Benzhydroles and nitriles upon gold-catalysed conversion deliver symmetrical ethers and/or N-substituted carboxylic amides. While with most phosphane ligands tested, the dominating product is always the ether, with the trimesitylene ligand the amides are the major products. The reaction conditions are much milder than those reported previously. Mechanistic control experiments with a chiral alcohol prove the intermediacy of carbenium ions, further studies with not readily ionisable alcohols indicate that for the benzhydroles the carbenium ions and gold(I)-hydroxy complexes are intermediates.

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Section: Resultsmentioning

confidence: 99%

Gold Catalysis: Alkyl Migration in the Addition of Alcohols to Nitriles

Ibrahim¹,

Hashmi

Röminger

2011

Adv Synth Catal

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“…Benzyl [172][173][174][175][176][177] , allyl 175,[178][179][180][181][182][183][184] and propargyl 175,185,186 alcohols 6 were treated with various nucleophiles in the presence of I 2 (2-20 mol%) and formed different types of products (Scheme 24, Table 20). Tertiary alcohols underwent elimination of water in the absence of nucleophiles providing the corresponding alkenes such as 59 (R 1 = R 2 = R 4 = H), in high yields (Scheme 24).…”

Section: Molecular Iodine-catalyzed Approachesmentioning

confidence: 99%

Alcohols in direct carbon-carbon and carbon-heteroatom bond-forming reactions: recent advances

Ajvazi¹,

Stavber²

2018

Arkivoc

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In recent years, nucleophilic substitution of alcohols leading to the formation of the C-C and C-heteroatom bonds has become an attractive process used in the synthesis of organic compounds, offering a potential impact on the environment, since water is the only by-product of the reaction. A comprehensive compilation of methods for the activation and displacement of a hydroxyl group covering the last seventeen years is the objective of the present review.

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“…[33] The scope of the reactions is broad: benzylic alcohols as well as tert-butanol and tert-butyl acetate were treated with a wide array of nitriles to generate the corresponding amides (Scheme 27). The authors hypothesize that the polarization of iodine in the nitrile, a polar solvent, might allow the activation of an alcohol to induce the formation of a carbocation intermediate.…”

Section: Miscellaneousmentioning

confidence: 99%

Ritter Reaction: Recent Catalytic Developments

2011

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The Ritter reaction is a method of choice for the production of amides, which are versatile intermediates in organic synthesis and compounds of interest in natural product synthesis. Recent efforts have been directed towards the development of catalytic versions for the development of more eco‐friendly synthetic routes to amides. This review summarizes the recent progress in this area and covers new applications in the field of Ritter‐type and multicomponent reactions.

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Iodine-catalyzed one-pot synthesis of amides from nitriles via Ritter reaction

Cited by 65 publications

References 31 publications

Gold Catalysis: Alkyl Migration in the Addition of Alcohols to Nitriles

Gold Catalysis: Alkyl Migration in the Addition of Alcohols to Nitriles

Alcohols in direct carbon-carbon and carbon-heteroatom bond-forming reactions: recent advances

Ritter Reaction: Recent Catalytic Developments

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