Journal ArticleDOI
Cesium effect: high chemoselectivity in direct N-alkylation of amines
TLDR
The results demonstrated this methodology was highly chemoselective to favor mono-N-alkylation over dialkylation, offering wide applications in peptidomimetic syntheses.Abstract:
A novel method for the mono-N-alkylation of primary amines, diamines, and polyamines was developed using cesium bases in order to prepare secondary amines efficiently. A cesium base not only promoted alkylation of primary amines but also suppressed overalkylations of the produced secondary amines. Various amines, alkyl bromides, and alkyl sulfonates were examined, and the results demonstrated this methodology was highly chemoselective to favor mono-N-alkylation over dialkylation. In particular, use of either sterically demanding substrates or amino acid derivatives afforded the secondary amines exclusively, offering wide applications in peptidomimetic syntheses.read more
Citations
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Journal ArticleDOI
New Strategies for the Transition-Metal Catalyzed Synthesis of Aliphatic Amines.
TL;DR: This review aims to provide a concise overview of modern transition-metal catalyzed approaches to alkylamine synthesis and their functionalization.
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Deep eutectic solvents (DESs) as eco-friendly and sustainable solvent/catalyst systems in organic transformations
TL;DR: In this article, the use of environmentally benign and inexpensive eutectic solvents (DESs) as solvent and catalyst in the field of organic chemistry is discussed and compared.
Journal ArticleDOI
Cp*Ir-catalyzed N-alkylation of amines with alcohols. A versatile and atom economical method for the synthesis of amines
TL;DR: In this paper, a catalytic system consisting of [Cp ∗ IrCl 2 ] 2 /NaHCO 3 for the N-alkylation of amines with primary and secondary alcohols as alkylating reagents has been developed.
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[IrCl2Cp*(NHC)] Complexes as Highly Versatile Efficient Catalysts for the Cross-Coupling of Alcohols and Amines
TL;DR: The compound [IrCl(2)Cp*(I(nBu))] showed to be highly effective in the cross-coupling reactions of amines and alcohols, providing high yields in the production of unsymmetrical ethers and N-alkylated amines.
Journal ArticleDOI
Ruthenium catalysed N-alkylation of amines with alcohols
TL;DR: The conversion of primary amines into secondary amines has been achieved using alcohols as the alkylating agent, catalysed by [Ru(p-cymene)Cl2]2 and a bidentate phosphine ligand.
References
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Journal ArticleDOI
Improved Cs2CO3 Promoted O-Alkylation of Acids
TL;DR: Cesium carbonate mediated O-alkylation of carboxylic acids was efficiently carried out under mild in situ conditions to give the corresponding esters exclusively in this article, with no observed racemization.
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The 'Caesium Effect' Revisited.
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Synthese von selektiv N- funktionalisierten Polyamin-Derivaten
Wolfgang Fiedler,Manfred Hesse +1 more
TL;DR: Spermidine derivative 19 and spermine derivative 20, both selectively protected at both primary amino groups, have been Prepared from the free polyamines 2 and 3, respectively, in a direct approach.
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N-Alkylation of Primary and Secondary Amines by Alkyl Halides and Lithium Naphthalene
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NMR studies of interionic interactions in N-methylformamide
TL;DR: In this paper, the NMR chemical shifts of alkali and thallium(I) salts with various monovalent anions have been measured in N-methylformamide solution.