The first example of linear peptides containing a N-trifluoroethylated backbone amide linkage and the surprising solution dynamics observed by 19F NMR

Lu, Chao; DesMarteau, Darryl D.

doi:10.1016/j.jfluchem.2007.04.005

Cited by 8 publications

(8 citation statements)

References 25 publications

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“…Fluoroalkyliodonium salts have found some synthetic application as electrophilic fluoroalkylating reagents. ,,− For example, the reaction of indoles 427 with 2,2,2-trifluoroethyl(mesityl)-iodonium triflate 428 in the presence of base results in the highly C-3 selective trifluoroethylation to give products 429 in good yields (Scheme ). This reaction enables fast and efficient introduction of the trifluoroethyl group under mild conditions with high functional group tolerance.…”

Section: Synthetic Applications Of Trivalent Iodine Compoundsmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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The preparation, structure, and chemistry of hypervalent iodine compounds are reviewed with emphasis on their synthetic application. Compounds of iodine possess reactivity similar to that of transition metals, but have the advantage of environmental sustainability and efficient utilization of natural resources. These compounds are widely used in organic synthesis as selective oxidants and environmentally friendly reagents. Synthetic uses of hypervalent iodine reagents in halogenation reactions, various oxidations, rearrangements, aminations, C−C bond-forming reactions, and transition metal-catalyzed reactions are summarized and discussed. Recent discovery of hypervalent catalytic systems and recyclable reagents, and the development of new enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important achievement in the field of hypervalent iodine chemistry. One of the goals of this Review is to attract the attention of the scientific community as to the benefits of using hypervalent iodine compounds as an environmentally sustainable alternative to heavy metals.

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Section: Synthetic Applications Of Trivalent Iodine Compoundsmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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“…NMR spectroscopy has been widely used for the study of restricted rotation in amides from early [4] up to recent years [5]. Some very recent reports focus their interest on acetamides [6] and their a-substituted derivatives [1,7,8]. Phosphonoacetamides are interesting due to their capability of complexing different metals, and have found application in the diagnosis and treatment of several diseases [9], as extracting agents for alkaline, alkaline earth and transition metals [10], and as reaction catalysts [11].…”

Section: Introductionmentioning

confidence: 99%

NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamides

Orelli

Gruber

2009

Journal of Molecular Structure

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“…In our early research on the trifluoroethylation of a-amino acids and small peptides, it was found that the trifluoroethylated N-termini of linear dipeptides retained sufficient nucleophilicity to undergo intramolecular cyclization reactions to form cyclic dipeptides (2,DKPs). 1 This stimulated us to explore the possibility of building N-trifluoroethylated linear peptide bonds, for example, by deprotonating the trifluoroethylated aamino proton and using amino acid fluorides for the coupling reactions.…”

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confidence: 99%

“…1 This stimulated us to explore the possibility of building N-trifluoroethylated linear peptide bonds, for example, by deprotonating the trifluoroethylated aamino proton and using amino acid fluorides for the coupling reactions. 2 Further, by converting N a -protected amino acids into the corresponding acid chlorides, we were eventually able to construct the N-1H,1H-perfluoroalkylated linear peptide bonds. 3 In the modification of N-1H,1H-perfluoroalkylated a-amino acids and small peptides, several compounds that resulted from solvent reactions attracted our attention due to their unique structures.…”

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confidence: 99%