Facile preparation of <i>N-tert</i>-butyl amides under heat-, metal- and acid-free conditions by using <i>tert</i>-butyl nitrite (TBN) as a practical carbon source

Natarajan, Palani; Metin, Önder

doi:10.1039/d3cc01168b

Cited by 3 publications

(2 citation statements)

References 24 publications

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“…Since only 10% of the desired 3a was produced by the reaction of 1a and 2a in acetonitrile (CH 3 CN) medium ( Table 1 and entry 5). It is significant to note that TEMPO (2,2,6,6-tetramethylpiperidinoxy radical), a well-known radical quencher, was oxidized by tert -butyl nitrite (TBN), resulting in 1-oxopiperidin-1-ium, which prohibits TEMPO usage in the employed conditions of a radical quenching reaction [ 28 ].…”

Section: Resultsmentioning

confidence: 99%

A facile tert-butyl nitrite-assisted preparation of deamino graphitic carbon nitride (DA-gCN) as a photocatalyst for the C-H arylation of heteroarenes using anilines as radical source

NATARAJAN,

KOÇ,

METİN

2023

Turkish Journal of Chemistry

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In pristine graphitic carbon nitride (g-CN), amino groups often function as structural defects that trap photogenerated charges, resulting in low photocatalytic activity as well as reaction with nitrite, aldehyde, etc., ensuing in poor product yield. Without significantly altering the optical characteristics, the removal of amino groups is necessary to increase the photocatalytic activity and structural stability of pristine g-CN. The deamino graphitic carbon nitride ( DA-gCN-5 ) was prepared by tert -butyl nitrite (TBN)-treatment, characterized and used as a photocatalyst for the radical C-H arylation of heteroarenes using anilines as radical source. Indeed, the photophysical characteristics of DA-gCN-5 and those of pristine g-CN are very comparable, except that DA-gCN-5 has a fewer residual amino groups, higher crystallinity, and compressed structure with a different morphology. Moreover, DA-gCN-5 -catalyzed C-H arylation reaction offers greater product yield in a shorter reaction time compared to that of pristine g-CN in the coupling between heteroarenes and the in situ generated aryl diazonium salts from anilines under visible light irradiation. The amino groups in pristine g-CN absorbed the TBN that was added to convert aniline into the appropriate diazonium ions during the reaction. As a result, deamino graphitic carbon nitride produced by chemical treatment has better photophysical properties and catalytic activity than pristine g-CN. Additionally, this is the first method that uses diazotization reaction for the preparation of deamino graphitic carbon nitride, as far as we are aware.

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Section: Resultsmentioning

confidence: 99%

A facile tert-butyl nitrite-assisted preparation of deamino graphitic carbon nitride (DA-gCN) as a photocatalyst for the C-H arylation of heteroarenes using anilines as radical source

NATARAJAN,

KOÇ,

METİN

2023

Turkish Journal of Chemistry

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“…17 The title compound was prepared according to the general procedure (reducing the reaction time to 7 h) and purified by flash column chromatography to give a yellow oil: 81.1 mg, 64% yield; 1 N-(tert-Butyl)-3-phenylpropanamide (3ag). 18 The title compound was prepared according to the general procedure (150 °C, 20 h) and purified by flash column chromatography to give a colorless solid: 40.1 mg, 39% yield; mp 83.4−86.2 °C; 1 H NMR (600 MHz, CDCl 3 ) δ 7.29−7.26 (m, 2H), 7.20−7.19 (m, 3H), 5.18 (br, 1H), 2.93 (t, J = 7.6 Hz, 2H), 2.38 (t, J = 7.7 Hz, 2H), 1.28 (s, 9H);…”

Section: -Phenyl-1-(pizperidin-1-yl)propan-1-one (3ac) 9bmentioning

confidence: 99%

Copper-Catalyzed Borrowing Hydrogen Reaction for α-Alkylation of Amides with Alcohols

Xia,

Miao,

et al. 2024

J. Org. Chem.

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Dehydrogenative Electrochemical Synthesis of N‐Aryl‐3,4‐Dihydroquinolin‐2‐ones by Iodine(III)‐Mediated Coupling Reaction

Bieniek,

Mashtakov,

Schollmeyer

et al. 2023

Chemistry A European J

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Electrochemically generated hypervalent iodine(III) species are powerful reagents for oxidative C−N coupling reactions, providing access to valuable N‐heterocycles. A new electrocatalytic hypervalent iodine(III)‐mediated in‐cell synthesis of 1H‐N‐aryl‐3,4‐dihydroquinolin‐2‐ones by dehydrogenative C−N bond formation is presented. Catalytic amounts of the redox mediator, a low supporting electrolyte concentration and recycling of the solvent used make this method a sustainable alternative to electrochemical ex‐cell or conventional approaches. Furthermore, inexpensive, readily available electrode materials and a simple galvanostatic set‐up are applied. The broad functional group tolerance could be demonstrated by synthesizing 23 examples in yields up to 96 %, with one reaction being performed on a 10‐fold higher scale. Based on the obtained results a sound reaction mechanism could be proposed.

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Facile preparation of N-tert-butyl amides under heat-, metal- and acid-free conditions by using tert-butyl nitrite (TBN) as a practical carbon source

Abstract: tert-Butyl nitrite (TBN) is a nontoxic substance that has frequently been used as a source of nitrogen, oxygen, or nitric oxide (NO), but not for carbon source in chemical transformations....

Cited by 3 publications

References 24 publications

A facile tert-butyl nitrite-assisted preparation of deamino graphitic carbon nitride (DA-gCN) as a photocatalyst for the C-H arylation of heteroarenes using anilines as radical source

A facile tert-butyl nitrite-assisted preparation of deamino graphitic carbon nitride (DA-gCN) as a photocatalyst for the C-H arylation of heteroarenes using anilines as radical source

Copper-Catalyzed Borrowing Hydrogen Reaction for α-Alkylation of Amides with Alcohols

Dehydrogenative Electrochemical Synthesis of N‐Aryl‐3,4‐Dihydroquinolin‐2‐ones by Iodine(III)‐Mediated Coupling Reaction

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