A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph<sub>3</sub>/<i>n</i>-chlorobenzotriazole system

Rouhi-Saadabad, Hamed; Akhlaghinia, Batool

doi:10.1080/10426507.2015.1024313

Cited by 4 publications

(1 citation statement)

References 73 publications

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“…Akhlaghinia [ 99 ] group presented a fast, metal‐free, one‐pot, and novel amide and sulfonamide bond formation from corresponding carboxylic acids, α‐amino acids, and sulfonic acids using PPh 3 /NCBT/amine system. The developed reaction has been shown good functional group tolerance with high yields (NCBT: N ‐chlorbenzotriazole) (Scheme 52).…”

Section: Coupling Reactionsmentioning

confidence: 99%

A new outlook in oxidative transformations and coupling reactions via in situ generation of organic chloramines

Govada

Reddy

2022

Applied Organom Chemis

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Owing to their various modes of coordinating and oxidizing reactivity, organic chloramines represent versatile building blocks for the synthesis of an ample range of multiatomic organic compounds. The present review focuses on synthetic methodologies using their dichotomous nature, which is the basis of their reactivity as oxidant and substrate. This is the first ever review covering the extensive applications of this large class of N–Cl compounds (organic chloramines) especially using one‐pot reaction strategies for various organic transformations, and construction of bonds such as chlorination (C–Cl, S–Cl), oxidation (C=O), cross‐coupling (C–N, CONR, S–N), cyclization, substitution, rearrangement, and catalysis, have been described, briefly to highlight important aspects of the organic chloramines in organic synthesis.

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Section: Coupling Reactionsmentioning

confidence: 99%

A new outlook in oxidative transformations and coupling reactions via in situ generation of organic chloramines

Govada

Reddy

2022

Applied Organom Chemis

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Synthesis of 2‐(Pentafluoro‐λ⁶‐sulfanyl)acetamides and Impact of the Fluorinated Group on the Lipophilicity

Mastalerz,

Verret,

Paquin

2024

Eur J Org Chem

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The synthesis of N‐(2‐SF5‐ethyl)amides is described via an amidation reaction between 2‐(pentafluoro‐λ6‐sulfanyl)acetic acid, the SF5‐containing building block, and various amines. A total of 27 examples of SF5‐containing amides were synthesized, with yields going from 43% to quantitative isolated yield. We showed that a N‐(2‐SF5‐ethyl)amide could be converted to a N‐(2‐SF5‐ethyl)amine and a SF5‐containing oxadiazoles. Finally, the effect of the SF5 substituent on the lipophilicity of the amide of a model compound was evaluated.

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Amide Synthesis through the In Situ Generation of Chloro- and Imido-Phosphonium Salts

2020

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We describe a methodology for the amidation of carboxylic acids by generating phosphonium salts in situ from N-chlorophthalimide and triphenylphosphine. Aliphatic, benzylic, and aromatic carboxylic acids can be transformed into their amide counter parts using primary and secondary amines. This functional group interconversion is achieved at room temperature in good to excellent yields. Mechanistic work shows the in situ formation of chloro- and imido-phosphonium salts that react as activating agents for carboxylic acids and generate an acyloxy-phosphonium species.

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A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph₃/n-chlorobenzotriazole system

Cited by 4 publications

References 73 publications

A new outlook in oxidative transformations and coupling reactions via in situ generation of organic chloramines

A new outlook in oxidative transformations and coupling reactions via in situ generation of organic chloramines

Synthesis of 2‐(Pentafluoro‐λ⁶‐sulfanyl)acetamides and Impact of the Fluorinated Group on the Lipophilicity

Amide Synthesis through the In Situ Generation of Chloro- and Imido-Phosphonium Salts

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A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph3/n-chlorobenzotriazole system

Cited by 4 publications

References 73 publications

A new outlook in oxidative transformations and coupling reactions via in situ generation of organic chloramines

A new outlook in oxidative transformations and coupling reactions via in situ generation of organic chloramines

Synthesis of 2‐(Pentafluoro‐λ6‐sulfanyl)acetamides and Impact of the Fluorinated Group on the Lipophilicity

Amide Synthesis through the In Situ Generation of Chloro- and Imido-Phosphonium Salts

Contact Info

Product

Resources

About

A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph₃/n-chlorobenzotriazole system

Synthesis of 2‐(Pentafluoro‐λ⁶‐sulfanyl)acetamides and Impact of the Fluorinated Group on the Lipophilicity