A comparison of microwave-accelerated and conventionally heated iodination reactions of some arenes and heteroarenes, using ortho-periodic acid as the oxidant

Molecules

Volumn 10, Issue 2, 2005, Pages 401-406

  Sosnowski, Maciej ^a   Skulski, Lech ^a  

^a MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

Diiodine; Microwave irradiation; ortho periodic acid as oxidant; Oxidation; Oxidative iodination of activated arenes and heteroarenes

Indexed keywords

2 PERIODIC ACID; INORGANIC ACID; OXIDIZING AGENT; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

CONFERENCE PAPER; IODINATION; MICROWAVE RADIATION; OXIDATION; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 18244409073     PISSN: 14203049     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/10020401     Document Type: Conference Paper

References (20)

1. a) Microwave-Enhanced Chemistry Fundamentals, Sample Preparation and Application. Kingston, H. M.; Haswell, S. J., Eds.; American Chemical Society: Washington, D.C., 1997;
2. b) Microwaves in Organic Synthesis. Loupy, A., Ed.; Wiley-VCH: Weinheim, 2002;
3. Microwave Synthesis; Chemistry at the Speed of Light. Hayes, B. L., Ed.; CEM Publishing: Matthews, NC, 2002.
4. Perreaux, L.; Loupy, A. A tentative realization of microwave effects in organic synthesis according to the reaction medium, and mechanistic consideration. Tetrahedron 2001, 57, 9199-9223. A review.
5. Lindstroem, P.; Tierney, J.; Whathey, B.; Westman, J. Microwave assisted organic synthesis - a review. Tetrahedron 2001, 57, 9225-9283.
6. Fini, A.; Breccia, A. Chemistry by Microwaves. Pure Appl. Chem. 1999, 71, 573-579. A review.
7. Sosnowski, M.; Skulski, L. Microwave-Accelerated Iodination of Some Aromatic Amines, Using Urea-Hydrogen Peroxide Addition Compound (UHP) as the Oxidant. Molecules 2002, 7, 867-870. Avail. at http://www.mdpi.org/molecules. Previously, the same results were presented at the Sixth Electronic Conference on Synthetic Organic Chemistry (ECSOC-6, http://www.mdpi.net/ecsoc-6), September 1-30, 2002 (paper E006).
8. Sosnowski, M., Skulski, L., Wolowik, K. Microwave-Accelerated or Conventionally Heated Iodination Reactions of Some Aromatic Amines, Using ortho-Periodic Acid as the Oxidant. Molecules 2004, 9, 617-621. Avail. at http://www.mdpi.org/molecules
9. Paolini, L.; Petricci, E.; Corelli, F.; Botta, M. Synthesis 2003, 1039-1042.
10. Bogdal, D.; Lukasiewicz, M.; Pielichowski, J. Green Chem. 2004, 6, 110-113.
11. Merkushev, E. B. Advances in the Synthesis of Iodoaromatic Compounds. Synthesis 1988, 923-937.
12. Skulski, L. Organic Iodine(I, III and V) Chemistry: 10 Years of Development at the Medical University of Warsaw, Poland (1990-2000). Molecules 2000, 5, 1331-1371. See pp 1332-1345. Avail at http://www.mdpi.org/molecules
13. 6 (the Suzuki reagent) to be an efficient iodinating agent for a series of polyalkylated benzenes, as well as some polycyclic and heterocyclic aromatic compounds. The reactions were mostly carried out at 60-90 °C in acetic acid - water with a little concd sulfuric acid. For more details see: a) Suzuki, H.; Nakamura, K.; Goto, R. The direct iodination of polyalkylbenzenes bearing bulky groups. Bull. Chem. Soc. Jpn. 1966, 39, 128-131; b) Fatiadi, A. J. New Applications of Periodic Acid and Periodates in Organic and Bio-Organic Chemistry. Synthesis 1974, 229-272. See pp. 230 and 242-243; c) Fatiadi, A. J. In Synthetic Reagents, Vol. 4; Pizey, J. S., Ed.; Halsted Press - Wiley: New York, 1981. See pp. 184-185.
14. 6 (the Suzuki reagent) to be an efficient iodinating agent for a series of polyalkylated benzenes, as well as some polycyclic and heterocyclic aromatic compounds. The reactions were mostly carried out at 60-90 °C in acetic acid - water with a little concd sulfuric acid. For more details see: a) Suzuki, H.; Nakamura, K.; Goto, R. The direct iodination of polyalkylbenzenes bearing bulky groups. Bull. Chem. Soc. Jpn. 1966, 39, 128-131; b) Fatiadi, A. J. New Applications of Periodic Acid and Periodates in Organic and Bio-Organic Chemistry. Synthesis 1974, 229-272. See pp. 230 and 242-243; c) Fatiadi, A. J. In Synthetic Reagents, Vol. 4; Pizey, J. S., Ed.; Halsted Press - Wiley: New York, 1981. See pp. 184-185.
15. 6 (the Suzuki reagent) to be an efficient iodinating agent for a series of polyalkylated benzenes, as well as some polycyclic and heterocyclic aromatic compounds. The reactions were mostly carried out at 60-90 °C in acetic acid - water with a little concd sulfuric acid. For more details see: a) Suzuki, H.; Nakamura, K.; Goto, R. The direct iodination of polyalkylbenzenes bearing bulky groups. Bull. Chem. Soc. Jpn. 1966, 39, 128-131; b) Fatiadi, A. J. New Applications of Periodic Acid and Periodates in Organic and Bio-Organic Chemistry. Synthesis 1974, 229-272. See pp. 230 and 242-243; c) Fatiadi, A. J. In Synthetic Reagents, Vol. 4; Pizey, J. S., Ed.; Halsted Press - Wiley: New York, 1981. See pp. 184-185.
16. Lulinski, P. Studies on Novel Methods of the Iodination of Aromatic Compounds. Doctoral Dissertation, Faculty of Pharmacy, Medical University of Warsaw, Poland, 2002, (in Polish).
17. Dictionary of Organic Compounds, 6th ed.; Chapman & Hall: London, 1996.
18. Novikov, A. N.; Grigor'ev, M. G. Effect of the nature of oxidants on the direct iodination of benzil. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 1977, 20, 1716-1917; [Chem. Abstr. 1978, 88, 89293]. The crude diiodobenzil was resolved there into its 3,3′-,2,2′- and 4,4′-diiodinated components by fractional crystallization.
19. Novikov, A. N.; Grigor'ev, M. G. Effect of the nature of oxidants on the direct iodination of benzil. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 1977, 20, 1716-1917; [Chem. Abstr. 1978, 88, 89293]. The crude diiodobenzil was resolved there into its 3,3′-,2,2′- and 4,4′-diiodinated components by fractional crystallization.
20. Kraszkiewicz, L.; Sosnowski, M.; Skulski, L. Easy, inexpensive and effective oxidative iodination of deactivated arenes in sulfuric acic. Tetrahedron 2004, 60, 9113-9119.