Pyrrolidide formation as a side reaction during activation of carboxylic acids by phosphonium salt coupling reagents

1999 ◽  
Vol 6 (4) ◽  
pp. 243-245 ◽  
Author(s):  
Jordi Alsina ◽  
George Barany ◽  
Fernando Albericio ◽  
Steven A. Kates
Keyword(s):  
Carboxylic Acids ◽  
Phosphonium Salt ◽  
Side Reaction ◽  
Coupling Reagents

scholarly journals Silicon compounds as stoichiometric coupling reagents for direct amidation

2021 ◽  
Author(s):  
Joshua J. Davies ◽  
D. Christopher Braddock ◽  
Paul D. Lickiss
Keyword(s):  
Carboxylic Acids ◽  
Coupling Reagents ◽  
Silicon Compounds ◽  
Direct Amidation

This review covers all the reported use of stoichiometric silicon reagents for direct amidation of carboxylic acids with amines, commencing with the first example in 1969 up until April 2021. 

scholarly journals Site-specific Umpolung amidation of carboxylic acids via triplet synergistic catalysis

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yunyun Ning ◽  
Shuaishuai Wang ◽  
Muzi Li ◽  
Jie Han ◽  
Chengjian Zhu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Amide Bond ◽  
Coupling Reagents ◽  
Complex Molecules ◽  
Bond Forming ◽  
Synergistic Catalysis ◽  
Wide Range ◽  
Amidation Reaction ◽  
Forming Methods

AbstractDevelopment of catalytic amide bond-forming methods is important because they could potentially address the existing limitations of classical methods using superstoichiometric activating reagents. In this paper, we disclose an Umpolung amidation reaction of carboxylic acids with nitroarenes and nitroalkanes enabled by the triplet synergistic catalysis of FeI2, P(V)/P(III) and photoredox catalysis, which avoids the production of byproducts from stoichiometric coupling reagents. A wide range of carboxylic acids, including aliphatic, aromatic and alkenyl acids participate smoothly in such reactions, generating structurally diverse amides in good yields (86 examples, up to 97% yield). This Umpolung amidation strategy opens a method to address challenging regioselectivity issues between nucleophilic functional groups, and complements the functional group compatibility of the classical amidation protocols. The synthetic robustness of the reaction is demonstrated by late-stage modification of complex molecules and gram-scale applications.

Total Synthesis of Dehydrodidemnin B. Use of Uronium and Phosphonium Salt Coupling Reagents in Peptide Synthesis in Solution†

1997 ◽  
Vol 62 (2) ◽  
pp. 354-366 ◽  
Author(s):  
Gemma Jou ◽  
Isabel González ◽  
Fernando Albericio ◽  
Paul Lloyd-Williams ◽  
Ernest Giralt
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Phosphonium Salt ◽  
Coupling Reagents

Ynamide: A New Coupling Reagent for Amide and Peptide Synthesis

Synlett ◽  
2017 ◽  
Vol 28 (14) ◽  
pp. 1663-1670 ◽  
Author(s):  
Long Hu ◽  
Junfeng Zhao
Keyword(s):  
Peptide Synthesis ◽  
Phosphonium Salt ◽  
Peptide Fragment ◽  
Coupling Reagents ◽  
Development History ◽  
Coupling Reagent ◽  
History Of ◽  
Fragment Condensation ◽  
Carbodiimide Coupling ◽  
Guanidinium Salt

The discovery and application of ynamide coupling reagents is highlighted with a brief summary of the development history of coupling reagents in amide and peptide synthesis. As novel coupling reagents, ynamides are not only effective for simple amide and dipeptide synthesis but also can be used for peptide fragment condensation. More importantly, no racemization was detected during the activation of α-chiral carboxylic acids by employing ynamide coupling reagents.1 Introduction2 Carbodiimide Coupling Reagents3 Uronium/Guanidinium Salt Coupling Reagents4 Phosphonium Salt Coupling Reagents5 Ethoxyacetylene as a Coupling Reagent6 Ynamine Coupling Reagents7 Ynamide Coupling Reagents8 Summary and Outlook

scholarly journals OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis

Synthesis ◽  
2020 ◽  
Vol 52 (21) ◽  
pp. 3189-3210
Author(s):  
Ayman El-Faham ◽  
Fernando Albericio ◽  
Srinivasa Rao Manne ◽  
Beatriz G. de la Torre
Keyword(s):  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Coupling Efficiency ◽  
Side Reaction ◽  
Solution Phase ◽  
Amide Bond ◽  
Side Reactions ◽  
Phosphonium Salts ◽  
Coupling Reagents ◽  
Peptide Chemistry

AbstractOxymaPure [ethyl 2-cyano-2-(hydroxyimino)acetate] is an exceptional reagent with which to suppress racemization and enhance coupling efficiency during amide bond formation. The tremendous popularity of OxymaPure has led to the development of several Oxyma-based reagents. OxymaPure and its derived reagents are widely used in solid- and solution-phase peptide chemistry. This review summarizes the recent developments and applications of OxymaPure and Oxyma-based reagents in peptide chemistry, in particular in solution-phase chemistry. Moreover, the side reaction associated with OxymaPure is also discussed.1 Introduction2 Oxyma-Based Coupling Reagents2.1 Aminium/Uronium Salts of OxymaPure2.2 Phosphonium Salts of OxymaPure2.3 Oxyma-Based Phosphates2.4 Sulfonate Esters of OxymaPure2.5 Benzoate Esters of OxymaPure2.6 Carbonates of OxymaPure Derivatives3 OxymaPure Derivatives4 Other Oxime-Based Additives and Coupling Reagents5 Side Reactions Using OxymaPure Derivatives6 Conclusion7 List of Abbreviations

ChemInform Abstract: Total Synthesis of Dehydrodidemnin B. Use of Uronium and Phosphonium Salt Coupling Reagents in Peptide Synthesis in Solution.

ChemInform ◽  
2010 ◽  
Vol 28 (20) ◽  
pp. no-no ◽  
Author(s):  
G. JOU ◽  
I. GONZALEZ ◽  
F. ALBERICIO ◽  
P. LLOYD-WILLIAMS ◽  
E. GIRALT
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Phosphonium Salt ◽  
Coupling Reagents

A Simple and Mild Esterification Method for Carboxylic Acids Using Sulfonate-type Coupling Reagents

Synthesis ◽  
1975 ◽  
Vol 1975 (07) ◽  
pp. 456-458 ◽  
Author(s):  
Masumi ITOH ◽  
Daijiro HAGIWARA ◽  
Jiyoji NOTANI
Keyword(s):  
Carboxylic Acids ◽  
Coupling Reagents ◽  
Type Coupling

scholarly journals An Efficient Metal-Free Oxidative Esterification and Amination of Benzyl C–H Bond

Molecules ◽  
2020 ◽  
Vol 25 (7) ◽  
pp. 1527
Author(s):  
Saiwen Liu ◽  
Ru Chen ◽  
Guowen He ◽  
Jin Zhang
Keyword(s):  
Carboxylic Acids ◽  
Oxidative Coupling ◽  
Coupling Reactions ◽  
Coupling Reagents ◽  
Oxidative Esterification ◽  
Metal Free ◽  
High Yields ◽  
Oxidative Coupling Reactions

An esterification and amination of benzylic C–H bonds was developed by using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under metal- and iodide-free conditions. Both carboxylic acids and amines could be used as ideal coupling partners for the oxidative coupling reactions with various diarylmethanes. A close to equal amount of coupling reagents was enough to afford the product in good to high yields.

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