Radical additions of aryl iodides to arenes are facilitated by oxidative rearomatization with dioxygen

Journal of the American Chemical Society

Volumn 128, Issue 42, 2006, Pages 13706-13707

  Curran, Dennis P ^a   Keller, Adam I ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; BIPHENYL 4 CARBOXYLIC ACID METHYL ESTER; CARBOXYLIC ACID DERIVATIVE; IODIDE; METHYL 4 IODOBENZOATE; OXYGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

ADDITION REACTION; AROMATIZATION; ARTICLE; CHEMICAL STRUCTURE; GAS; GAS CHROMATOGRAPHY; OXIDATION; REACTION ANALYSIS; REAROMATIZATION; STRUCTURE ANALYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 33750350313     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066077q     Document Type: Article

References (22)

1. Review: Studer, A. In Radicals in Organic Synthesis; 1st ed.; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, p 44-60.
2. Representative recent examples: (a) Nunez, A.; Sanchez, A.; Burgos, C.; Alvarez-Builla, J. Tetrahedron 2004, 60, 6217-6224.
3. (b) McLoughlin, P. T. F.; Clyne, M. A.; Aldabbagh, F. Tetrahedron 2004, 60, 8065-8071.
4. (e) Bennasar, M. L.; Roca, T.; Ferrando, F. Tetrahedron Lett. 2004, 45, 5605-5609.
5. For peroxide-mediated reactions, see: (a) Menes-Arzate, M.; Martinez, R.; Cruz-Almanza, R.; Muchowski, J. M.; Osornio, Y. M.; Miranda, L. D. J. Org. Chem. 2004, 69, 4001-4004.
6. For reductive additions catalyzed by benzeneselenol, see: (a) Crich, D.; Patel, M. Org. Lett. 2005, 7, 3625-3628 and references therein.
7. a) Beckwith, A. L. J.; Bowry, V. W.; Bowman, W. R.; Mann, E.; Parr, J.; Storey, J. M. D. Angew. Chem., Int. Ed. 2004, 43, 95-98.
8. (b) Oxidation by hydroperoxy radicals formed in situ by autoxidation has been suggested: Bennasar, M. L.; Roca, T.; Ferrando, F. J. Org. Chem. 2005, 70, 9077-9080.
9. Sluder, A. Chem.-Eur. J. 2001, 7, 1159-1164.
10. (a) Teichert, A.; Jantos, K.; Harms, K.; Studer, A. Org. Lett. 2004, 6, 3477-3480.
11. (b) Leroi, C.; Berlin, D.; Dufils, P. E.; Gigmes, D.; Marque, S.; Tordo, P.; Couturier, J. L.; Guerret, O.; Ciufolini, M. A. Org. Lett. 2003, 5, 4943-4945.
12. Studer, A.; Bossart, M. Tetrahedron 2001, 57, 9649-9667.
13. -1 at 80 °C. See (a) Chatgilialoglu, C. Chem. Rev. 1995, 95, 1229-1251.
14. (b) Curran, D. P.; Jasperse, C. P.; Totleben, M. J. J. Org. Chem. 1991, 56, 7169-7172.
15. Scaiano, J. C.; Stewart, L. C. J. Am. Chem. Soc. 1983, 105, 3609-3614.
16. Chatgilialoglu, C.; Guarini, A.; Guerrini, A.; Seconi, G. J. Org. Chem. 1992, 57, 2207-2208.
17. Analogously, under suitable conditions, oxygen does not inhibit the tin hydride reduction of alkyl iodides, but instead participates in a chain oxygenation reaction. Nakamura, E.; Inubushi, T.; Aoki, S.; Machii, D. J. Am. Chem. Soc. 1991, 113, 8980-8982.
18. a) Hendry, D. G.; Schuetzle, D. J. Am. Chem. Soc. 1975, 97, 7123-7127.
19. (b) Maillard, B.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1983, 105, 5095-5099.
20. (c) Howard, J. A. In Peroxyl Radicals; Alfassi, Z. B., Ed.; Wiley: Chichester, U.K. 1997; p 283-334.
21. -1 at 25 °C: Chatgilialoglu, C.; Timokhin, V. I.; Zaborovskiy, A. B.; Lutsyk, D. S.; Prystansky, R. E. Chem. Commun. 1999, 405-406. However, tertiary peroxy radicals can be considerably less reactive than the hydroperoxy radical. See ref 13.
22. We also checked for oxidation of benzene; no phenol was detected (GC).