Photocatalytic alkoxylation of benzene with 3-cyano-1-methylquinolinium ion

Optics Express

Volumn 20, Issue 102, 2012, Pages A360-A365

  Ohkubo, Kei ^a   Kobayashi, Takaki ^a   Fukuzumi, Shunichi ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ADDITION REACTIONS; IONS; QUANTUM YIELD;

ACETONITRILE SOLUTIONS; ALKOXYLATION; NANOSECOND LASERS; NUCLEOPHILIC ADDITIONS; ONE POT; PHOTO-CATALYTIC; PHOTO-INDUCED ELECTRON TRANSFER; PHOTO-IRRADIATION; PHOTOCATALYTIC REACTIONS; RADICAL CATIONS; SINGLET EXCITED STATE;

BENZENE;

EID: 84858974573     PISSN: None     EISSN: 10944087     Source Type: Journal    
DOI: 10.1364/OE.20.00A360     Document Type: Article

References (22)

1. H. Fiege, H.-W. Voges, T. Hamamoto, S. Umemura, T. Iwata, H. Miki, Y. Fujita, H.-J. Buysch, D. Garbe, and W. Paulus, Phenol derivatives in Ullmann's encyclopedia of industrial chemistry (Wiley-VCH, Weinheim 2002).
2. J. J. Li and D. S. Johnson, Modern Drug Synthesis (Wiley, Hoboken, 2010).
3. S. Enthaler and A. Company, “Palladium-catalysed hydroxylation and alkoxylation,” Chem. Soc. Rev. 40(10), 4912-4924 (2011).
4. G. S. Hiers and F. D. Hager, “Anisole,” Org. Syn. Coll. 1, 58 (1941).
5. J. M. Miller, K. H. So, and J. H. Clark, “Fluoride ion promoted synthesis of alkyl phenyl ethers,” Can. J. Chem. 57(14), 1887-1889 (1979).
6. R. Molinari and T. Poerio, “Remarks on studies for direct production of phenol in conventional and membrane reactors,” Asia-Pac. J. Chem. Eng. 5(1), 191-206 (2010).
7. T. Maeyama and N. Mikami, “Nucleophilic substitution within the photoionized van der Waals complex: generation of C6H5NH3+ from C6H3Cl-NH3,” J. Am. Chem. Soc. 110(21), 7238-7239 (1988).
8. T. Maeyama and N. Mikami, “Nucleophilic substitution within the photoionized van der Waals complex chlorobenzene-ammonia,” J. Phys. Chem. 94(18), 6973-6977 (1990).
9. T. Maeyama and N. Mikami, “Intracluster ion molecule reactions within the photoionized van der Waals complexes of fluorobenzene with ammonia and with water,” J. Phys. Chem. 95(19), 7197-7204 (1991).
10. H. Tachikawa, “Intramolecular SN2 reaction caused by photoionization of benzene chloride-NH3 complex: direct ab initio molecular dynamics study,” J. Phys. Chem. A 110(1), 153-159 (2006).
11. D. Tholmann and H.-F. Grützmacher, “Aromatic substitution of halobenzenes in the gas phase: A kinetic study by FT-ICR spectrometry,” Chem. Phys. Lett. 163(2-3), 225-229 (1989).
12. D. Tholmann and H.-F. Grützmacher, “Reactions of dihalobenzene radical cations with ammonia in the gas phase. Reactivity pattern for nucleophilic aromatic substitution,” J. Am. Chem. Soc. 113(9), 3281-3287 (1991).
13. G. Bouchoux, R. Flammang, J. De Winter, and P. Gerbaux, “Reactions of ionized methyl benzoate with methyl isocyanide in the gas phase: nucleophilic aromatic substitutions vs hydrogen migrations,” J. Phys. Chem. A 113(41), 11075-11083 (2009).
14. G. Bouchoux, J. De Winter, R. Flammang, and P. Gerbaux, “Aromatic substitution reactions between ionized benzene derivatives and neutral methyl isocyanide,” J. Phys. Chem. A 114(27), 7408-7416 (2010).
15. E. Baciocchi, T. Del Giacco, O. Lanzalunga, P. Mencarelli, and B. Procacci, “Photosensitized oxidation of alkyl phenyl sulfoxides. C-S bond cleavage in alkyl phenyl sulfoxide radical cations,” J. Org. Chem. 73(15), 56755682 (2008).
16. K. Ohkubo, T. Kobayashi, and S. Fukuzumi, “Direct oxygenation of benzene to phenol using quinolinium ions as homogeneous photocatalysts,” Angew. Chem. Int. Ed. Engl. 50(37), 8652-8655 (2011).
17. R. D. Mair and A. J. Graupner, “Determination of organic peroxides by iodine liberation procedures,” Anal. Chem. 36(1), 194-204 (1964).
18. S. Fukuzumi, S. Kuroda, and T. Tanaka, “Flavin analogue-metal ion complexes acting as efficient photocatalysts in the oxidation of p-methylbenzyl alcohol by oxygen under irradiation with visible light,” J. Am. Chem. Soc. 107(11), 3020-3027 (1985).
19. S. Fukuzumi, M. Ishikawa, and T. Tanaka, “Mechanisms of photo-oxidation of NADH model compounds by oxygen,” J. Chem. Soc. Perkin Trans. 2(8), 1037-1045 (1989).
20. H. Kitaguchi, K. Ohkubo, S. Ogo, and S. Fukuzumi, “Electron-transfer oxidation properties of unsaturated fatty acids and mechanistic insight into lipoxygenases,” J. Phys. Chem. A 110(5), 1718-1725 (2006).
21. H. Togo and M. Katohgi, “Synthetic uses of organohypervalent iodine compounds through radical pathways,” Synlett 2001(5), 565-581 (2001).
22. S. Furuyama and H. Togo, “An efficient preparation of chroman derivatives from 3-aryl-1-propanols and related compounds with 1, 3-diiodo-5, 5-dimethylhydantoin under irradiation conditions,” Synlett 2010(15), 2325-2329 (2010).