Light‐Induced Dealkylation of Benzamides in Aqueous Solution

Cybularczyk‐Cecotka, Martyna; Kamińska, Agnieszka; Jopek, Zuzanna; Giedyk, Maciej

doi:10.1002/ejoc.202200913

Eur J Org Chem

2022

DOI: 10.1002/ejoc.202200913

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Light‐Induced Dealkylation of Benzamides in Aqueous Solution

Martyna Cybularczyk‐Cecotka

Agnieszka Kamińska

Zuzanna Jopek

et al.

Abstract: Supporting information for this article is given via a link at the end of the document.

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Cited by 5 publications

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References 27 publications

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“…The reactions of N-ethyl-N-isopropylbenzamide (3), N,Ndiethylbenzamide (4), N-isopropyl-N-benzylbenzamide (5), Nmethyl-N-isopropylbenzamide (6), and N-isopropyl-Nphenylbenzamide (7) As shown in Scheme 3A, the parallel kinetic isotope experiments of 1a and 1a-D gave a KIE value of 1.23, indicating that the cleavage of aryl C−H bond is not the rate-limiting step. Based on this data and previous reports 16 , a plausible reaction mechanism for 1a is proposed in Scheme 3B. Upon heating, sulfate radical anion is generated from persulfate and then undergoes hydrogen atom transfer (HAT) with 1a to form alkyl radical intermediate I.…”

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confidence: 59%

Facile Synthesis of Isoindolinones via Radical-Mediated Intramolecular Coupling of Two C–H Bonds

Han

Huang

et al. 2023

Synlett

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A metal-free method for the construction of 3,3-dimethyl isoindolinones via radical-mediated intramolecular coupling of two C-H bonds of N,N-diisopropyl benzamides was developed. The reactions can proceed in moderate to high yield and with excellent chemoselectivity. A reaction sequence of the formation of an alkyl radical via oxidative cleavage of alkyl C-H bond and the formation of lactam ring via intramolecular homolytic aromatic substitution was proposed.

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supporting

confidence: 59%

Facile Synthesis of Isoindolinones via Radical-Mediated Intramolecular Coupling of Two C–H Bonds

Han

Huang

et al. 2023

Synlett

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Atmospheric Oxygen Facilitated Oxidative Amidation to α-Ketoamides and Unusual One Carbon Degradative Amidation to N-Alkyl Amides

Jadav,

Vankar,

Gupta

et al. 2023

J. Org. Chem.

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A mild, transition-metal-free novel synthetic approach for the construction of C�O and C−N bonds has been demonstrated. Easily accessible gem-dibromoalkenes under similar conditions form oxidative amidation product α-ketoamides and unusual degradative amidation product N-alkyl amides by simply changing the amine substitute. Atmospheric air containing molecular oxygen proved to be an ideal oxidant for an amidation reaction. Under similar conditions, the electron-deficient gem-dibromoalkenes play a dual role with different formamides forming novel oxidative amidation products and by the state of art neighboring group participation of amine to unusual one-carbon degradative amidation products.

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TMSN₃ Initiated Electrochemical Mono-Dealkylation of Tertiary Amides

Ding,

Liu,

Jiang

et al. 2024

J. Org. Chem.

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N-Dealkylation of amides is a general process in living organisms and organic synthetic chemistry, but an efficient chemical approach for this transformation has not been explored. Herein, we report an electrochemical method for the monodealkylation of a wide range of tertiary amides, including benzamides, alkyl amides, lactams, and sulfonamides. The reaction proceeds smoothly under mild conditions using TMSN 3 as the initiator and is not limited to deethylation or demethylation. This protocol enables the large synthesis, providing a valuable tool for synthetic organic chemistry.

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Light‐Induced Dealkylation of Benzamides in Aqueous Solution

Abstract: Supporting information for this article is given via a link at the end of the document.

Cited by 5 publications

References 27 publications

Facile Synthesis of Isoindolinones via Radical-Mediated Intramolecular Coupling of Two C–H Bonds

Facile Synthesis of Isoindolinones via Radical-Mediated Intramolecular Coupling of Two C–H Bonds

Atmospheric Oxygen Facilitated Oxidative Amidation to α-Ketoamides and Unusual One Carbon Degradative Amidation to N-Alkyl Amides

TMSN₃ Initiated Electrochemical Mono-Dealkylation of Tertiary Amides

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Light‐Induced Dealkylation of Benzamides in Aqueous Solution

Abstract: Supporting information for this article is given via a link at the end of the document.

Cited by 5 publications

References 27 publications

Facile Synthesis of Isoindolinones via Radical-Mediated Intramolecular Coupling of Two C–H Bonds

Facile Synthesis of Isoindolinones via Radical-Mediated Intramolecular Coupling of Two C–H Bonds

Atmospheric Oxygen Facilitated Oxidative Amidation to α-Ketoamides and Unusual One Carbon Degradative Amidation to N-Alkyl Amides

TMSN3 Initiated Electrochemical Mono-Dealkylation of Tertiary Amides

Contact Info

Product

Resources

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TMSN₃ Initiated Electrochemical Mono-Dealkylation of Tertiary Amides