Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and <i>N</i>‐Halosuccinimide

Mukhopadhyay, Sushobhan; Batra, Sanjay

doi:10.1002/chem.201803347

Cited by 34 publications

(20 citation statements)

References 59 publications

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“…1 H NMR (500 MHz, CDCl 3 ): δ =7.46 (d, J =5.3 Hz, 1 H), 7.09 (d, J =5.3 Hz, 1 H), 3.90 (s, 3 H) ppm; 13 C NMR (126 MHz, CDCl 3 ): δ =160.5, 131.5, 132.2, 124.2, 117.2, 51.5 ppm. Physical and spectroscopic data were in agreement with those reported in the literature …”

Section: Methodssupporting

confidence: 90%

Microwave‐Assisted Synthesis of Sulfurated Heterocycles with Herbicidal Activity: Reaction of 2‐Alkynylbenzoic Acids with Lawesson's Reagent

et al. 2019

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The reactivity of 2‐alkynylbenzoic acids toward Lawesson's reagent (LR) under microwave irradiation (300 W, 100 °C, CH2Cl2) was assessed. It was found that, depending on reaction conditions, either a dithionation‐ or a monothionation‐cycloisomerization process takes place with formation of important sulfurated heterocycles. In particular, using 1 equivalent of LR for 1 h, dithionation occurred, with formation of benzo[c]thiophene‐1(3H)‐thiones or 1H‐isothiochromene‐1‐thiones, while with 0.5 equiv. of LR for 10–30 min, monothionated products were selectively obtained (benzo[c]thiophen‐1(3H)‐ones or 1H‐isothiochromen‐1‐ones). The regiochemical output of the process strongly depended on the substitution pattern of the starting 2‐alkynylbenzoic acid derivatives. These compounds were also assayed as potential herbicides by assessing their phytotoxic activity on seedling growth and development of the model species Arabidopsis thaliana. All compounds, to different extents, influenced the morpho‐physiological parameters that were monitored; in particular, the fresh weight (FW) was significantly affected, with ED50 values ranging from 4.81–63.7 μM.

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Section: Methodssupporting

confidence: 90%

Microwave‐Assisted Synthesis of Sulfurated Heterocycles with Herbicidal Activity: Reaction of 2‐Alkynylbenzoic Acids with Lawesson's Reagent

et al. 2019

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“…Ethyl 3-chlorobenzoate 8b [ 36 ]. The reaction of ethanol 7b (7 mg, 0.150 mmol) according to the general procedure afforded 13 mg (47%) of product 8b , isolated as a colorless oil; IR (neat) cm −1 : 2924, 1727, 1573, 1466, 1370, 1293, 1281, 1256, 915, and 749; 1 H NMR (500 MHz, CDCl 3 ): δ 8.03 (s, 1H), 7.94 (d, J = 7.5 Hz, 1H), 7.56–7.52 (m, 1H), 7.39 (t, J = 7.5 Hz, 1H), 4.39 (q, J = 7.0 Hz, 2H), and 1.41 (t, J = 7.0 Hz, 3H); HRMS (APCI-positive): calcd for C 9 H 10 ClO 2 ([M + H]) + : 185.0369, found: 185.0389.…”

Section: Methodsmentioning

confidence: 99%

Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines

et al. 2021

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Hypervalent iodine heterocycles represent one of the important classes of hypervalent iodine reagents with many applications in organic synthesis. This paper reports a simple and convenient synthesis of benziodazolones by the reaction of readily available iodobenzamides with m-chloroperoxybenzoic acid in acetonitrile at room temperature. The structure of one of these new iodine heterocycles was confirmed by X-ray analysis. In combination with PPh3 and pyridine, these benziodazolones can smoothly react with alcohols or amines to produce the corresponding esters or amides of 3-chlorobenzoic acid, respectively. It was found that the novel benziodazolone reagent reacts more efficiently than the analogous benziodoxolone reagent in this esterification.

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“…Batra et al demonstrated that anilines are converted to the respective haloarenes in the presence of N-halosuccinimides and excess amount of NaNO 2 via a diazonium salt intermediate in DMF (iv). [18] Control experiments revealed that this halogenation is actually mediated by a NO 2 X species. Mo et al used electrochemistry to promote halogenations of diazonium salts with NBS, CH 2 I 2 , or LiCl (v).…”

Section: Introductionmentioning

confidence: 99%

Photochemical Sandmeyer‐type Halogenation of Arenediazonium Salts

Sivendran

Belitz

Prendes

et al. 2022

Chemistry A European J

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Trihalide salts were found to efficiently promote photochemical dediazotizing halogenations of diazonium salts. In contrast to classical Sandmeyer reactions, no metal catalysts are required to achieve high yields and outstanding selectivities for halogenation over competing hydridodediazotization. Convenient protocols are disclosed for synthetically meaningful brominations, iodinations, and chlorinations of diversely functionalized derivatives.

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Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N‐Halosuccinimide

Cited by 34 publications

References 59 publications

Microwave‐Assisted Synthesis of Sulfurated Heterocycles with Herbicidal Activity: Reaction of 2‐Alkynylbenzoic Acids with Lawesson's Reagent

Microwave‐Assisted Synthesis of Sulfurated Heterocycles with Herbicidal Activity: Reaction of 2‐Alkynylbenzoic Acids with Lawesson's Reagent

Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines

Photochemical Sandmeyer‐type Halogenation of Arenediazonium Salts

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