Journals / Turkish Journal of Chemistry / 2020 / Cilt: 44 - Sayı: 2

Arene diazonium saccharin intermediates: a greener and cost-effective alternative method for the preparation of aryl iodide

Pages
535–542
Publication Date
2022-11-04
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

The outstanding merits of the current protocol (a)included the partial recovering of saccharin and tetraethylammonium salt, (b) reduce the use of solvents and the reactionsteps due to eliminating separation and purification of intermediates, (c) good yield of the sterically hindered substrates,and (d) avoid the generation of heavy metal or corrosive waste.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:In the current protocol, the arene diazonium saccharin derivatives were initially produced from varioussubstituted aromatic amines; subsequently, these intermediates were treated with a greener organic iodide for thepreparation of the aryl iodide.
📊
Key Findings & Data:The arene diazonium saccharin intermediates could be stored in the liquid phaseinto a refrigerator for a long time with no significant loss activity.
💡
Conclusion & Impact:The outstanding merits of the current protocol (a)included the partial recovering of saccharin and tetraethylammonium salt, (b) reduce the use of solvents and the reactionsteps due to eliminating separation and purification of intermediates, (c) good yield of the sterically hindered substrates,and (d) avoid the generation of heavy metal or corrosive waste.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

In the current protocol, the arene diazonium saccharin derivatives were initially produced from varioussubstituted aromatic amines; subsequently, these intermediates were treated with a greener organic iodide for thepreparation of the aryl iodide. We tried to choose low-cost, commercially available, biodegradable, recoverable, ecofriendly, and safe reagents and solvents. The arene diazonium saccharin intermediates could be stored in the liquid phaseinto a refrigerator for a long time with no significant loss activity. The outstanding merits of the current protocol (a)included the partial recovering of saccharin and tetraethylammonium salt, (b) reduce the use of solvents and the reactionsteps due to eliminating separation and purification of intermediates, (c) good yield of the sterically hindered substrates,and (d) avoid the generation of heavy metal or corrosive waste.

🔖

Cite This Article

KHALIGH, N. G., JOHAN, M. R., SHAHNAVAZ, Z., ZAHARANI, L. (2022). Arene diazonium saccharin intermediates: a greener and cost-effective alternative method for the preparation of aryl iodide. Turkish Journal of Chemistry, Cilt: 44 - Sayı: 2, 535–542. https://ajindex.com/articles/601521

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (4)

  1. Wulfman DS. The Chemistry of Diazonium and Diazo Groups, Part 1. In: Patai S (editor). NY, USA: Wiley, 1978, pp. 250-252
  2. Khaligh NG. Telescopic synthesis of azo compounds via stable arenediazonium bis(trifluoromethane) sulfonimide salts by using tert-butyl nitrite. Dyes and Pigments 2017; 139: 556-560. doi: 10.1016/j.dyepig.2016.11.058 3. Beckwith ALJ, Meijs GF. Iododediazoniation of arenediazonium salts accompanied by aryl radical ring closure. Journal of Organic Chemistry 1987; 52 (10): 1922-1930. doi: 10.1021/jo00386a007 4. Khaligh NG. A facile and sustainable protocol to the preparation of aryl iodides using stable arenediazonium bis(trifluoromethylsulfonyl)imide salts via the telescopic process. Heteroatom Chemistry 2018; 29 (2): e21418. doi: 10.1002/hc.21418 5. Khaligh NG, Johan MR, Ching JJ. Saccharin: a cheap and mild acidic agent for the synthesis of azo dyes via telescoped dediazotization. Green Processing and Synthesis 2019; 8 (1): 24-29. doi: 10.1515/gps-2017-0133 6. Khaligh NG, Johan MR, Ching JJ. Saccharin and tert-butyl nitrite: Cheap and efficient reagents for the synthesis of 1,2,3-benzotriazine-4-(3H)-ones from 2-aminobenzamides under metal-free conditions. Australian Journal of Chemistry 2018; 71 (3): 186-189. doi: 10.1071/CH17590 7. Khaligh NG, Mihankhah T, Johan MR, Ching JJ. Saccharin: an efficient organocatalyst for the one-pot synthesis of 4-amido-cinnolines under metal and halogen-free conditions. Monatshefte für Chemie 2018; 149 (6): 1083-1087. doi: 10.1007/s00706-018-2174-2 8. Khaligh NG. Recent advances and applications of tert-butyl nitrite (TBN) in organic synthesis. Mini-reviews in Organic Chemistry 2020; 17 (1): 1-22. doi: 10.2174/1570193X15666181029141019 9. Khaligh NG. Recently applications of tert-butyl nitrite in organic synthesis-Part I. Current Organic Chemistry 2018; 22 (11): 1120-1138. doi: 10.2174/1385272822666180430124840 10. Yu SB, Watson AD. Metal-based X-ray contrast media. Chemical Review 1999; 99 (9): 2353-2378. doi: 10.1021/cr980441p 11. Serjeant EP, Dempsey B. Ionisation constants of organic acids in aqueous solution. International Union of Pure and Applied Chemistry (IUPAC). IUPAC Chemical Data Series No
  3. NY, USA: Pergamon Press Inc., 1979
  4. Larsen JC. Artificial sweeteners. Nutrafoods 2012; 11 (1): 3-9. doi: 10.1007/s13749-012-0003-5 13. Weihrauch MR, Diehl V. Artificial sweeteners-do they bear a carcinogenic risk? Annals of Oncology 2004; 15 (10): 1460-1465. doi: 10.1093/annonc/mdh256 14. J