How to cite this paper
Kapłon, K., Demchuk, O., Wieczorek, M & Pietrusiewicz, K. (2014). Bronsted acid catalyzed direct oxidative arylation of 1,4-naphthoquinone.Current Chemistry Letters, 3(1), 23-36.
Refrences
1. Lin A. J., and Sartorelli A. C. (1976) Potential bioreductive alkylating-agents .7. Antitumor effects of phenyl-substituted 2-chloromethyl-3-phenyl-1,4-naphthoquinones. J. Med. Chem., 19(11), 1336-1338.
2. Morrison R. K., Brown D. E., Oleson J. J., and Cooney D. A. (1970) Oral toxicology studies with lapachol. Toxicol. Appl. Pharm., 17(1), 1-9.
3. Tamayo N., Echavarren A. M., and Paredes M. C. (1991) Palladium-catalyzed coupling of 2-bromonaphthoquinones with stannanes - a concise synthesis of antibiotics ws-5995-a and ws-5995-c and related-compounds. J. Org. Chem., 56(23), 6488-6491.
4. Snipes C. E., Chang C., and Floss H. G. (1979) Biosynthesis of the antibiotic granaticin. J. Am. Chem. Soc., 101(3), 701-706.
5. Crosby I. T., Rose M. L., Collis M. P., De Bruyn P. J., Keep P. L. C., and Robertson A. D. (2008) Antiviral agents. I. Synthesis and antiviral evaluation of trimeric naphthoquinone analogues of conocurvone. Aust. J. Chem., 61(10), 768-784.
6. Boyd M. R. C. J. H., Decosterd L. A., Gustafson K. R. (1998) Antiviral naphthoquinone compounds, compositions and uses thereof.
7. Malerich J. P., Maimone T. J., Elliott G. I., and Trauner D. (2005) Biomimetic synthesis of antimalarial naphthoquinones. J. Am. Chem. Soc., 127(17), 6276-6283.
8. Heymann H., and Fieser L. F. (1948) Naphthoquinone antimalarials .19. Antirespiratory study of protein binding. J. Pharmacol. Exp. Ther., 94(2), 97-111.
9. Ioset J. R., Marston A., Gupta M. P., and Hostettmann K. (1998) Antifungal and larvicidal meroterpenoid naphthoquinones and a naphthoxirene from the roots of cordia linnaei. Phytochemistry, 47(5), 729-734.
10. Perry N. B., Blunt J. W., and Munro M. H. G. (1991) Cytotoxic and antifungal c-14-amines from a new-zealand ascidian - major lipid components of pseudodistoma-novaezelandiae. Aust. J. Chem., 44(4), 627-633.
11. Ahn J. H., Cho S. Y., Ha J. D., Chu S. Y., Jung S. H., Jung Y. S., Baek J. Y., Choi I. K., Shin E. Y., Kang S. K., Kim S. S., Cheon H. G., Yang S. D., and Choi J. K. (2002) Synthesis and ptp1b inhibition of 1,2-naphthoquinone derivatives as potent anti-diabetic agents. Bioorg. Med. Chem. Lett., 12(15), 1941-1946.
12. Griffiths J. (2002) Ullmann & apos; s encyclopedia of industrial chemistry. Wiley-VCH Verlag GmbH & Co. KGaA.
13. Demchuk O. M., Kielar K., and Pietrusiewicz K. M. (2011) Rational design of novel ligands for environmentally benign cross-coupling reactions. Pure Appl. Chem., 83(3), 633-644.
14. Demchuk O. M., Yoruk B., Blackburn T., and Snieckus V. (2006) A mixed naphthyl-phenyl phosphine ligand motif for suzuki, heck, and hydrodehalogenation reactions. Synlett, 18), 2908-2913.
15. Lamblin M., Naturale G., Dessolin J., and Felpin F. X. (2012) Direct c-h arylation of quinones with anilines. Synlett, 11, 1621-1624.
16. Itahara T. (1985) Oxidative coupling of quinones and aromatic-compounds by palladium(ii) acetate. J. Org. Chem., 50(26), 5546-5550.
17. Yoshida K., Yamanaka Y., and Ueno Y. (1994) Synthesis of new dilactone-type fluorescent dyes and their fluorochromic properties. Chem. Lett., 11), 2051-2054.
18. Demchuk O. M., and Pietrusiewicz K. M. (2009) New and efficient protocol for arylation of quinones. Synlett, 7, 1149-1153.
19. Singh P. K., Rohtagi B. K., and Khanna R. N. (1992) Arylation of quinones with aryl mercuryl chloride catalyzed by lithium palladium-chloride. Synthetic Commun., 22(7), 987-993.
20. Zhao Y. K., Zhang Y. X., Wang J. T., Li H. J., Wu L. M., and Liu Z. Q. (2010) Synthesis of aryl-substituted 1,4-benzoquinone via palladium(ii)-catalyzed decarboxylative coupling of arene carboxylate with 1,4-benzoquinone. Synlett, 15, 2352-2356.
21. Fujiwara Y., Domingo V., Seiple I. B., Gianatassio R., Del Bel M., and Baran P. S. (2011) Practical c-h functionalization of quinones with boronic acids. J. Am. Chem. Soc., 133(10), 3292-3295.
22. Zhang H. B., Liu L., Chen Y. J., Wang D., and Li C. J. (2006) Synthesis of aryl-substituted 1,4-benzoquinone via water-promoted and In(OTf)3-catalyzed in situ conjugate addition-dehydrogenation of aromatic compounds to 1,4-benzoquinone in water. Adv. Synth. Catal., 348(1-2), 229-235.
23. Liu B., Ji S. J., Su X. M., and Wang S. Y. (2008) Novel synthesis of 3-indolylquinones catalyzed by molecular iodine under ultrasonic irradiation. Synthetic Commun., 38(8), 1279-1290.
24. Blackburn C., and Griffiths J. (1982) Naphthoquinone coloring matters .5. Reactions of nn-dialkylarylamines with 1,4-naphthoquinones - a convenient route to 2-(4-nn-dialkylaminoaryl)-1,4-naphthoquinones. J. Chem. Res.-S., 12, 320-321.
25. Kielar K., and Demchuk O. M. (2012) Synthesis of Sym-Phos {dicyclohexyl [3-(2,4,6-trimethoxyphenyl)-4-methoxynaphth-2-yl]phosphine} ligand and its application in suzuki-miyaura reaction”. Chemik, 66, 585.
26. Perez P., Domingo L. R., Duque-Norena M., and Chamorro E. (2009) A condensed-to-atom nucleophilicity index. An application to the director effects on the electrophilic aromatic substitutions. J. Mol. Struc.-Theochem., 895(1-3), 86-91.
27. All calculation were performed on desktop WinVista powered (intel q6600, 8g ram) PC by means of wawefunction software Spartan’10.
28. Jasi?ski R. (2012) Exploration of regiospecificity phenomenon in [2+3] cycloaddition reactions between arylnitrones and trans-substituted nitroethenes on the basis of the reactivity indices theory. Curr. Chem. Lett., 1, 157-162.
29. Spartan’10, wavefunction, inc., irvine, ca.
30. Shao Y. M. L. F., Jung Y., Kussmann J., Ochsenfeld C., Brown S.T., Gilbert A.T.B., Slipchenko L.V., Levchenko S.V., O’neill D.P., Distasio Jr. R.A., Lochan R.C., Wang T., Beran G.J.O., Besley N.A., Herbert J.M., Lin C.Y., Van Voorhis T., Chien S.H., Sodt A., Steele R.P., Rassolov V.A., Maslen P.E., Korambath P.P., Adamson R.D., Austin B., Baker J., Byrd E.F.C., Dachsel H., Doerksen R.J., Dreuw A., Dunietz B.D., Dutoi A.D., Furlani T.R., Gwaltney S.R., Heyden A., Hirata S., Hsu C-P., Kedziora G., Khalliulin R.Z., Klunzinger P., Lee A.M., Lee M.S., Liang W.Z., Lotan I., Nair N., Peters B., Proynov E.I., Pieniazek P.A., Rhee Y.M., Ritchie J., Rosta E., Sherrill C.D., Simmonett A.C., Subotnik J.E.,. Woodcock Iii H.L, Zhang W., Bell A.T., Chakraborty A.K., Chipman D.M., Keil F.J., Warshel A., Hehre W.J., Schaefer H.F., Kong J., Krylov A.I., Gill P.M.W.And Head-Gordon M. (2006) Phys. Chem. Chem. Phys., 8, 3172.
31. Parr R. G., and Yang W. (1989) Density-functional theory of atoms and molecules, Oxford University Press.
32. Pérez, P.; Domingo, L.R.; Aizman, A.; Contreras, R. (2007) The Electrophilicity Index in Organic Chemistry, in Toro-Labbe, A. (Ed.) Theoretical Aspects of Chemical Reactivity; Elsevier, Amsterdam, Vol. 19, 139-201 and references cited therein.
33. Chattaraj P. K., Giri S., and Duley S. (2011) Update 2 of: Electrophilicity index. Chem. Rev., 111(2), 43-75.
34. Perez P., Domingo L. R., Aurell A. J., and Contreras R. (2003) Quantitative characterization of the global electrophilicity pattern of some reagents involved in 1,3-dipolar cycloaddition reactions. Tetrahedron, 59(17), 3117-3125.
35. Jasinski R., and Baranski A. (2010) Reactivity of (e)-2-aryl-1-cyano-1-nitroethenes in carbo and hetero Diels-Alder reactions with cyclopentadiene: A dft study. J. Mol. Struc.-Theochem., 949(1-3), 8-13.
2. Morrison R. K., Brown D. E., Oleson J. J., and Cooney D. A. (1970) Oral toxicology studies with lapachol. Toxicol. Appl. Pharm., 17(1), 1-9.
3. Tamayo N., Echavarren A. M., and Paredes M. C. (1991) Palladium-catalyzed coupling of 2-bromonaphthoquinones with stannanes - a concise synthesis of antibiotics ws-5995-a and ws-5995-c and related-compounds. J. Org. Chem., 56(23), 6488-6491.
4. Snipes C. E., Chang C., and Floss H. G. (1979) Biosynthesis of the antibiotic granaticin. J. Am. Chem. Soc., 101(3), 701-706.
5. Crosby I. T., Rose M. L., Collis M. P., De Bruyn P. J., Keep P. L. C., and Robertson A. D. (2008) Antiviral agents. I. Synthesis and antiviral evaluation of trimeric naphthoquinone analogues of conocurvone. Aust. J. Chem., 61(10), 768-784.
6. Boyd M. R. C. J. H., Decosterd L. A., Gustafson K. R. (1998) Antiviral naphthoquinone compounds, compositions and uses thereof.
7. Malerich J. P., Maimone T. J., Elliott G. I., and Trauner D. (2005) Biomimetic synthesis of antimalarial naphthoquinones. J. Am. Chem. Soc., 127(17), 6276-6283.
8. Heymann H., and Fieser L. F. (1948) Naphthoquinone antimalarials .19. Antirespiratory study of protein binding. J. Pharmacol. Exp. Ther., 94(2), 97-111.
9. Ioset J. R., Marston A., Gupta M. P., and Hostettmann K. (1998) Antifungal and larvicidal meroterpenoid naphthoquinones and a naphthoxirene from the roots of cordia linnaei. Phytochemistry, 47(5), 729-734.
10. Perry N. B., Blunt J. W., and Munro M. H. G. (1991) Cytotoxic and antifungal c-14-amines from a new-zealand ascidian - major lipid components of pseudodistoma-novaezelandiae. Aust. J. Chem., 44(4), 627-633.
11. Ahn J. H., Cho S. Y., Ha J. D., Chu S. Y., Jung S. H., Jung Y. S., Baek J. Y., Choi I. K., Shin E. Y., Kang S. K., Kim S. S., Cheon H. G., Yang S. D., and Choi J. K. (2002) Synthesis and ptp1b inhibition of 1,2-naphthoquinone derivatives as potent anti-diabetic agents. Bioorg. Med. Chem. Lett., 12(15), 1941-1946.
12. Griffiths J. (2002) Ullmann & apos; s encyclopedia of industrial chemistry. Wiley-VCH Verlag GmbH & Co. KGaA.
13. Demchuk O. M., Kielar K., and Pietrusiewicz K. M. (2011) Rational design of novel ligands for environmentally benign cross-coupling reactions. Pure Appl. Chem., 83(3), 633-644.
14. Demchuk O. M., Yoruk B., Blackburn T., and Snieckus V. (2006) A mixed naphthyl-phenyl phosphine ligand motif for suzuki, heck, and hydrodehalogenation reactions. Synlett, 18), 2908-2913.
15. Lamblin M., Naturale G., Dessolin J., and Felpin F. X. (2012) Direct c-h arylation of quinones with anilines. Synlett, 11, 1621-1624.
16. Itahara T. (1985) Oxidative coupling of quinones and aromatic-compounds by palladium(ii) acetate. J. Org. Chem., 50(26), 5546-5550.
17. Yoshida K., Yamanaka Y., and Ueno Y. (1994) Synthesis of new dilactone-type fluorescent dyes and their fluorochromic properties. Chem. Lett., 11), 2051-2054.
18. Demchuk O. M., and Pietrusiewicz K. M. (2009) New and efficient protocol for arylation of quinones. Synlett, 7, 1149-1153.
19. Singh P. K., Rohtagi B. K., and Khanna R. N. (1992) Arylation of quinones with aryl mercuryl chloride catalyzed by lithium palladium-chloride. Synthetic Commun., 22(7), 987-993.
20. Zhao Y. K., Zhang Y. X., Wang J. T., Li H. J., Wu L. M., and Liu Z. Q. (2010) Synthesis of aryl-substituted 1,4-benzoquinone via palladium(ii)-catalyzed decarboxylative coupling of arene carboxylate with 1,4-benzoquinone. Synlett, 15, 2352-2356.
21. Fujiwara Y., Domingo V., Seiple I. B., Gianatassio R., Del Bel M., and Baran P. S. (2011) Practical c-h functionalization of quinones with boronic acids. J. Am. Chem. Soc., 133(10), 3292-3295.
22. Zhang H. B., Liu L., Chen Y. J., Wang D., and Li C. J. (2006) Synthesis of aryl-substituted 1,4-benzoquinone via water-promoted and In(OTf)3-catalyzed in situ conjugate addition-dehydrogenation of aromatic compounds to 1,4-benzoquinone in water. Adv. Synth. Catal., 348(1-2), 229-235.
23. Liu B., Ji S. J., Su X. M., and Wang S. Y. (2008) Novel synthesis of 3-indolylquinones catalyzed by molecular iodine under ultrasonic irradiation. Synthetic Commun., 38(8), 1279-1290.
24. Blackburn C., and Griffiths J. (1982) Naphthoquinone coloring matters .5. Reactions of nn-dialkylarylamines with 1,4-naphthoquinones - a convenient route to 2-(4-nn-dialkylaminoaryl)-1,4-naphthoquinones. J. Chem. Res.-S., 12, 320-321.
25. Kielar K., and Demchuk O. M. (2012) Synthesis of Sym-Phos {dicyclohexyl [3-(2,4,6-trimethoxyphenyl)-4-methoxynaphth-2-yl]phosphine} ligand and its application in suzuki-miyaura reaction”. Chemik, 66, 585.
26. Perez P., Domingo L. R., Duque-Norena M., and Chamorro E. (2009) A condensed-to-atom nucleophilicity index. An application to the director effects on the electrophilic aromatic substitutions. J. Mol. Struc.-Theochem., 895(1-3), 86-91.
27. All calculation were performed on desktop WinVista powered (intel q6600, 8g ram) PC by means of wawefunction software Spartan’10.
28. Jasi?ski R. (2012) Exploration of regiospecificity phenomenon in [2+3] cycloaddition reactions between arylnitrones and trans-substituted nitroethenes on the basis of the reactivity indices theory. Curr. Chem. Lett., 1, 157-162.
29. Spartan’10, wavefunction, inc., irvine, ca.
30. Shao Y. M. L. F., Jung Y., Kussmann J., Ochsenfeld C., Brown S.T., Gilbert A.T.B., Slipchenko L.V., Levchenko S.V., O’neill D.P., Distasio Jr. R.A., Lochan R.C., Wang T., Beran G.J.O., Besley N.A., Herbert J.M., Lin C.Y., Van Voorhis T., Chien S.H., Sodt A., Steele R.P., Rassolov V.A., Maslen P.E., Korambath P.P., Adamson R.D., Austin B., Baker J., Byrd E.F.C., Dachsel H., Doerksen R.J., Dreuw A., Dunietz B.D., Dutoi A.D., Furlani T.R., Gwaltney S.R., Heyden A., Hirata S., Hsu C-P., Kedziora G., Khalliulin R.Z., Klunzinger P., Lee A.M., Lee M.S., Liang W.Z., Lotan I., Nair N., Peters B., Proynov E.I., Pieniazek P.A., Rhee Y.M., Ritchie J., Rosta E., Sherrill C.D., Simmonett A.C., Subotnik J.E.,. Woodcock Iii H.L, Zhang W., Bell A.T., Chakraborty A.K., Chipman D.M., Keil F.J., Warshel A., Hehre W.J., Schaefer H.F., Kong J., Krylov A.I., Gill P.M.W.And Head-Gordon M. (2006) Phys. Chem. Chem. Phys., 8, 3172.
31. Parr R. G., and Yang W. (1989) Density-functional theory of atoms and molecules, Oxford University Press.
32. Pérez, P.; Domingo, L.R.; Aizman, A.; Contreras, R. (2007) The Electrophilicity Index in Organic Chemistry, in Toro-Labbe, A. (Ed.) Theoretical Aspects of Chemical Reactivity; Elsevier, Amsterdam, Vol. 19, 139-201 and references cited therein.
33. Chattaraj P. K., Giri S., and Duley S. (2011) Update 2 of: Electrophilicity index. Chem. Rev., 111(2), 43-75.
34. Perez P., Domingo L. R., Aurell A. J., and Contreras R. (2003) Quantitative characterization of the global electrophilicity pattern of some reagents involved in 1,3-dipolar cycloaddition reactions. Tetrahedron, 59(17), 3117-3125.
35. Jasinski R., and Baranski A. (2010) Reactivity of (e)-2-aryl-1-cyano-1-nitroethenes in carbo and hetero Diels-Alder reactions with cyclopentadiene: A dft study. J. Mol. Struc.-Theochem., 949(1-3), 8-13.