Can-mediated oxidative free radical reactions in an ionic liquid

Synthetic Communications

Volumn 33, Issue 2, 2003, Pages 213-222

  Bar, Gregory ^a   Bini, Fabien ^a   Parsons, Andrew F ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Ionic liquids; Radical reactions

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM TETRAFLUOROBORATE; AMMONIUM NITRATE; BORINIC ACID DERIVATIVE; CERIUM; DICHLOROMETHANE; FREE RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CYCLIZATION; MOLECULAR INTERACTION; OXIDATION; RADICAL REACTION; REACTION ANALYSIS; REACTION OPTIMIZATION;

EID: 0037272408     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120015703     Document Type: Article

References (26)

1. Nair, V.; Mathew, J.; Prabhakaran, J. Carbon-carbon bond forming reactions mediated by cerium(IV) reagents. Chem. Soc. Rev. 1997, 127-132.
2. (a) Baciocchi, E.; Paolobelli, A.B.; Ruzziconi, R. Cerium(IV) ammonium nitrate promoted oxidative cyclization of dimethyl 4-pentenylmalonate. Tetrahedron 1992, 48, 4617-4622; (b) D'Annibale, A.; Pesce, A.; Resta, S.; Trogolo, C. Ceric ammonium nitrate promoted free radical cyclization reactions leading to β-lactams. Tetrahedron Lett. 1997, 38, 1829-1832.
3. (a) Baciocchi, E.; Paolobelli, A.B.; Ruzziconi, R. Cerium(IV) ammonium nitrate promoted oxidative cyclization of dimethyl 4-pentenylmalonate. Tetrahedron 1992, 48, 4617-4622; (b) D'Annibale, A.; Pesce, A.; Resta, S.; Trogolo, C. Ceric ammonium nitrate promoted free radical cyclization reactions leading to β-lactams. Tetrahedron Lett. 1997, 38, 1829-1832.
4. (a) Baciocchi, E.; Ruzziconi, R. Electronic and steric effects in the addition of electrophilic 1,3-dicarbonylalkyl radicals to styrenes. J. Org. Chem. 1991, 56, 4772-4778; (b) Schoop, A.; Greiving, H.; Göhrt, A. A new analogue of rocaglamide by an oxidative dihydrofuran synthesis. Tetrahedron Lett. 2000, 41, 1913-1916; (c) Kobayashi, K.; Tanaka, H.; Tanaka, K.; Yoneda, K.; Morikawa, O.; Konishi, H. One-step synthesis of furo[2,3-d]pyrimidine-2,4-(1H,3H)-diones using the CAN-mediated furan ring formation. Synth. Commun. 2000, 30, 4277; (d) Lee, Y.R.; Kim, B.S.; Kim, D.H. Ceric ammonium nitrate (CAN)-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds. Efficient synthesis of dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, dihydrofurophenalenones, and furonaphthoquinone natural products. Tetrahedron 2000, 56, 8845-8853; (e) Nair, V.; Mathew, J.; Alexander, S. Synthesis of spiroannulated dihydrofurans by cerium(IV) ammonium nitrate mediated addition of 1,3-dicarbonyl compounds to exocyclic alkenes. Synth. Commun. 1995, 25, 3981-3991; (f) Appendino, G.; Cravotto, G.; Palmisano, G.; Annunziata, R. Oxidative addition of 4-hydroxycoumarin to alkenes. An expeditious entry to 2,3-dihydro-4H-furo-[3,2-c][1]benzopyran-4-ones. Synth. Commun. 1996, 26, 3359-3371; (g) Yadav, J.S.; Reddy, B.V.S.; Reddy, K.B.; Raj, K.S.; Prasad, A.R. Ultrasound-accelerated synthesis of 3,4-dihydropyrimidin-2(1/H-ones with ceric ammonium nitrate. J. Chem. Soc., Perkin Trans. 1 2001, 1939-1941.
5. (a) Baciocchi, E.; Ruzziconi, R. Electronic and steric effects in the addition of electrophilic 1,3-dicarbonylalkyl radicals to styrenes. J. Org. Chem. 1991, 56, 4772-4778; (b) Schoop, A.; Greiving, H.; Göhrt, A. A new analogue of rocaglamide by an oxidative dihydrofuran synthesis. Tetrahedron Lett. 2000, 41, 1913-1916; (c) Kobayashi, K.; Tanaka, H.; Tanaka, K.; Yoneda, K.; Morikawa, O.; Konishi, H. One-step synthesis of furo[2,3-d]pyrimidine-2,4-(1H,3H)-diones using the CAN-mediated furan ring formation. Synth. Commun. 2000, 30, 4277; (d) Lee, Y.R.; Kim, B.S.; Kim, D.H. Ceric ammonium nitrate (CAN)-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds. Efficient synthesis of dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, dihydrofurophenalenones, and furonaphthoquinone natural products. Tetrahedron 2000, 56, 8845-8853; (e) Nair, V.; Mathew, J.; Alexander, S. Synthesis of spiroannulated dihydrofurans by cerium(IV) ammonium nitrate mediated addition of 1,3-dicarbonyl compounds to exocyclic alkenes. Synth. Commun. 1995, 25, 3981-3991; (f) Appendino, G.; Cravotto, G.; Palmisano, G.; Annunziata, R. Oxidative addition of 4-hydroxycoumarin to alkenes. An expeditious entry to 2,3-dihydro-4H-furo-[3,2-c][1]benzopyran-4-ones. Synth. Commun. 1996, 26, 3359-3371; (g) Yadav, J.S.; Reddy, B.V.S.; Reddy, K.B.; Raj, K.S.; Prasad, A.R. Ultrasound-accelerated synthesis of 3,4-dihydropyrimidin-2(1/H-ones with ceric ammonium nitrate. J. Chem. Soc., Perkin Trans. 1 2001, 1939-1941.
6. (a) Baciocchi, E.; Ruzziconi, R. Electronic and steric effects in the addition of electrophilic 1,3-dicarbonylalkyl radicals to styrenes. J. Org. Chem. 1991, 56, 4772-4778; (b) Schoop, A.; Greiving, H.; Göhrt, A. A new analogue of rocaglamide by an oxidative dihydrofuran synthesis. Tetrahedron Lett. 2000, 41, 1913-1916; (c) Kobayashi, K.; Tanaka, H.; Tanaka, K.; Yoneda, K.; Morikawa, O.; Konishi, H. One-step synthesis of furo[2,3-d]pyrimidine-2,4-(1H,3H)-diones using the CAN-mediated furan ring formation. Synth. Commun. 2000, 30, 4277; (d) Lee, Y.R.; Kim, B.S.; Kim, D.H. Ceric ammonium nitrate (CAN)-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds. Efficient synthesis of dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, dihydrofurophenalenones, and furonaphthoquinone natural products. Tetrahedron 2000, 56, 8845-8853; (e) Nair, V.; Mathew, J.; Alexander, S. Synthesis of spiroannulated dihydrofurans by cerium(IV) ammonium nitrate mediated addition of 1,3-dicarbonyl compounds to exocyclic alkenes. Synth. Commun. 1995, 25, 3981-3991; (f) Appendino, G.; Cravotto, G.; Palmisano, G.; Annunziata, R. Oxidative addition of 4-hydroxycoumarin to alkenes. An expeditious entry to 2,3-dihydro-4H-furo-[3,2-c][1]benzopyran-4-ones. Synth. Commun. 1996, 26, 3359-3371; (g) Yadav, J.S.; Reddy, B.V.S.; Reddy, K.B.; Raj, K.S.; Prasad, A.R. Ultrasound-accelerated synthesis of 3,4-dihydropyrimidin-2(1/H-ones with ceric ammonium nitrate. J. Chem. Soc., Perkin Trans. 1 2001, 1939-1941.
7. (a) Baciocchi, E.; Ruzziconi, R. Electronic and steric effects in the addition of electrophilic 1,3-dicarbonylalkyl radicals to styrenes. J. Org. Chem. 1991, 56, 4772-4778; (b) Schoop, A.; Greiving, H.; Göhrt, A. A new analogue of rocaglamide by an oxidative dihydrofuran synthesis. Tetrahedron Lett. 2000, 41, 1913-1916; (c) Kobayashi, K.; Tanaka, H.; Tanaka, K.; Yoneda, K.; Morikawa, O.; Konishi, H. One-step synthesis of furo[2,3-d]pyrimidine-2,4-(1H,3H)-diones using the CAN-mediated furan ring formation. Synth. Commun. 2000, 30, 4277; (d) Lee, Y.R.; Kim, B.S.; Kim, D.H. Ceric ammonium nitrate (CAN)-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds. Efficient synthesis of dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, dihydrofurophenalenones, and furonaphthoquinone natural products. Tetrahedron 2000, 56, 8845-8853; (e) Nair, V.; Mathew, J.; Alexander, S. Synthesis of spiroannulated dihydrofurans by cerium(IV) ammonium nitrate mediated addition of 1,3-dicarbonyl compounds to exocyclic alkenes. Synth. Commun. 1995, 25, 3981-3991; (f) Appendino, G.; Cravotto, G.; Palmisano, G.; Annunziata, R. Oxidative addition of 4-hydroxycoumarin to alkenes. An expeditious entry to 2,3-dihydro-4H-furo-[3,2-c][1]benzopyran-4-ones. Synth. Commun. 1996, 26, 3359-3371; (g) Yadav, J.S.; Reddy, B.V.S.; Reddy, K.B.; Raj, K.S.; Prasad, A.R. Ultrasound-accelerated synthesis of 3,4-dihydropyrimidin-2(1/H-ones with ceric ammonium nitrate. J. Chem. Soc., Perkin Trans. 1 2001, 1939-1941.
8. (a) Baciocchi, E.; Ruzziconi, R. Electronic and steric effects in the addition of electrophilic 1,3-dicarbonylalkyl radicals to styrenes. J. Org. Chem. 1991, 56, 4772-4778; (b) Schoop, A.; Greiving, H.; Göhrt, A. A new analogue of rocaglamide by an oxidative dihydrofuran synthesis. Tetrahedron Lett. 2000, 41, 1913-1916; (c) Kobayashi, K.; Tanaka, H.; Tanaka, K.; Yoneda, K.; Morikawa, O.; Konishi, H. One-step synthesis of furo[2,3-d]pyrimidine-2,4-(1H,3H)-diones using the CAN-mediated furan ring formation. Synth. Commun. 2000, 30, 4277; (d) Lee, Y.R.; Kim, B.S.; Kim, D.H. Ceric ammonium nitrate (CAN)-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds. Efficient synthesis of dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, dihydrofurophenalenones, and furonaphthoquinone natural products. Tetrahedron 2000, 56, 8845-8853; (e) Nair, V.; Mathew, J.; Alexander, S. Synthesis of spiroannulated dihydrofurans by cerium(IV) ammonium nitrate mediated addition of 1,3-dicarbonyl compounds to exocyclic alkenes. Synth. Commun. 1995, 25, 3981-3991; (f) Appendino, G.; Cravotto, G.; Palmisano, G.; Annunziata, R. Oxidative addition of 4-hydroxycoumarin to alkenes. An expeditious entry to 2,3-dihydro-4H-furo-[3,2-c][1]benzopyran-4-ones. Synth. Commun. 1996, 26, 3359-3371; (g) Yadav, J.S.; Reddy, B.V.S.; Reddy, K.B.; Raj, K.S.; Prasad, A.R. Ultrasound-accelerated synthesis of 3,4-dihydropyrimidin-2(1/H-ones with ceric ammonium nitrate. J. Chem. Soc., Perkin Trans. 1 2001, 1939-1941.
9. (a) Baciocchi, E.; Ruzziconi, R. Electronic and steric effects in the addition of electrophilic 1,3-dicarbonylalkyl radicals to styrenes. J. Org. Chem. 1991, 56, 4772-4778; (b) Schoop, A.; Greiving, H.; Göhrt, A. A new analogue of rocaglamide by an oxidative dihydrofuran synthesis. Tetrahedron Lett. 2000, 41, 1913-1916; (c) Kobayashi, K.; Tanaka, H.; Tanaka, K.; Yoneda, K.; Morikawa, O.; Konishi, H. One-step synthesis of furo[2,3-d]pyrimidine-2,4-(1H,3H)-diones using the CAN-mediated furan ring formation. Synth. Commun. 2000, 30, 4277; (d) Lee, Y.R.; Kim, B.S.; Kim, D.H. Ceric ammonium nitrate (CAN)-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds. Efficient synthesis of dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, dihydrofurophenalenones, and furonaphthoquinone natural products. Tetrahedron 2000, 56, 8845-8853; (e) Nair, V.; Mathew, J.; Alexander, S. Synthesis of spiroannulated dihydrofurans by cerium(IV) ammonium nitrate mediated addition of 1,3-dicarbonyl compounds to exocyclic alkenes. Synth. Commun. 1995, 25, 3981-3991; (f) Appendino, G.; Cravotto, G.; Palmisano, G.; Annunziata, R. Oxidative addition of 4-hydroxycoumarin to alkenes. An expeditious entry to 2,3-dihydro-4H-furo-[3,2-c][1]benzopyran-4-ones. Synth. Commun. 1996, 26, 3359-3371; (g) Yadav, J.S.; Reddy, B.V.S.; Reddy, K.B.; Raj, K.S.; Prasad, A.R. Ultrasound-accelerated synthesis of 3,4-dihydropyrimidin-2(1/H-ones with ceric ammonium nitrate. J. Chem. Soc., Perkin Trans. 1 2001, 1939-1941.
10. (a) Baciocchi, E.; Ruzziconi, R. Electronic and steric effects in the addition of electrophilic 1,3-dicarbonylalkyl radicals to styrenes. J. Org. Chem. 1991, 56, 4772-4778; (b) Schoop, A.; Greiving, H.; Göhrt, A. A new analogue of rocaglamide by an oxidative dihydrofuran synthesis. Tetrahedron Lett. 2000, 41, 1913-1916; (c) Kobayashi, K.; Tanaka, H.; Tanaka, K.; Yoneda, K.; Morikawa, O.; Konishi, H. One-step synthesis of furo[2,3-d]pyrimidine-2,4-(1H,3H)-diones using the CAN-mediated furan ring formation. Synth. Commun. 2000, 30, 4277; (d) Lee, Y.R.; Kim, B.S.; Kim, D.H. Ceric ammonium nitrate (CAN)-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds. Efficient synthesis of dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, dihydrofurophenalenones, and furonaphthoquinone natural products. Tetrahedron 2000, 56, 8845-8853; (e) Nair, V.; Mathew, J.; Alexander, S. Synthesis of spiroannulated dihydrofurans by cerium(IV) ammonium nitrate mediated addition of 1,3-dicarbonyl compounds to exocyclic alkenes. Synth. Commun. 1995, 25, 3981-3991; (f) Appendino, G.; Cravotto, G.; Palmisano, G.; Annunziata, R. Oxidative addition of 4-hydroxycoumarin to alkenes. An expeditious entry to 2,3-dihydro-4H-furo-[3,2-c][1]benzopyran-4-ones. Synth. Commun. 1996, 26, 3359-3371; (g) Yadav, J.S.; Reddy, B.V.S.; Reddy, K.B.; Raj, K.S.; Prasad, A.R. Ultrasound-accelerated synthesis of 3,4-dihydropyrimidin-2(1/H-ones with ceric ammonium nitrate. J. Chem. Soc., Perkin Trans. 1 2001, 1939-1941.
11. Baciocchi, E.; Giese, B.; Farshchi, H.; Ruzziconi, R. Relative rates for the addition reactions of the malonyl radical to substituted styrenes induced by cerium(IV) ammonium nitrate and tributyltin hydride. A comparison. J. Org. Chem. 1990, 55, 5688-5691.
12. (a) Nair, V.; Mathew, J.; Radhakrishnan, K.V. Oxidative addition of 1,3-dicarbonyl compounds to alkenes mediated by cerium(IV) ammonium nitrate and manganese(III) acetate: a comparative study. J. Chem. Soc., Perkin Trans. 1 1996, 1487-1492; (b) Nair, V.; Methew, J. Facile synthesis of dihydrofurans by the cerium(IV) ammonium mediated oxidative addition of 1,3-dicarbonyl compounds to cyclic and acyclic alkenes. Relative superiority over the manganese(III) acetate mediated process. J. Chem. Soc., Perkin Trans. 1 1995, 187-188.
13. (a) Nair, V.; Mathew, J.; Radhakrishnan, K.V. Oxidative addition of 1,3-dicarbonyl compounds to alkenes mediated by cerium(IV) ammonium nitrate and manganese(III) acetate: a comparative study. J. Chem. Soc., Perkin Trans. 1 1996, 1487-1492; (b) Nair, V.; Methew, J. Facile synthesis of dihydrofurans by the cerium(IV) ammonium mediated oxidative addition of 1,3-dicarbonyl compounds to cyclic and acyclic alkenes. Relative superiority over the manganese(III) acetate mediated process. J. Chem. Soc., Perkin Trans. 1 1995, 187-188.
14. (a) Welton, T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 1999, 99, 2071-2083; (b) Wasserscheid, P.; Keim, W. Ionic liquids-new "solutions" for transition metal catalysis. Angew. Chem. Int. Ed. 2000, 39, 3772-3789; (c) Earle, M.J.; Seddon, K.R. Ionic liquids. Green solvents for the future. Pure Appl. Chem. 2000, 72, 1391-1398.
15. (a) Welton, T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 1999, 99, 2071-2083; (b) Wasserscheid, P.; Keim, W. Ionic liquids-new "solutions" for transition metal catalysis. Angew. Chem. Int. Ed. 2000, 39, 3772-3789; (c) Earle, M.J.; Seddon, K.R. Ionic liquids. Green solvents for the future. Pure Appl. Chem. 2000, 72, 1391-1398.
16. (a) Welton, T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 1999, 99, 2071-2083; (b) Wasserscheid, P.; Keim, W. Ionic liquids-new "solutions" for transition metal catalysis. Angew. Chem. Int. Ed. 2000, 39, 3772-3789; (c) Earle, M.J.; Seddon, K.R. Ionic liquids. Green solvents for the future. Pure Appl. Chem. 2000, 72, 1391-1398.
17. Bar, G.; Parsons, A.F.; Thomas, C.B. Manganese(III) acetate mediated radical reactions in the presence of an ionic liquid. Chem. Commun. 2001, 1350-1351.
18. Holbrey, J.B.; Seddon, K.R. The phase behaviour of 1-alkyl-3-methylimidazolium tetrafluoroborates; ionic liquids and ionic liquid crystals. J. Chem. Soc., Dalton Trans. 1999, 2133-2139.
19. Nair, V.; Mathew, J.; Nair, L.G. Cerium(IV) ammonium nitrate mediated addition of 1,3-dicarbonyl compounds to dienes. Synth. Commun. 1996, 26, 4531-4538.
20. Kobayashi, K.; Sakashita, K.; Akamatsu, H.; Tanaka, K.; Uchida, M.; Uneda, T.; Kitamura, T.; Morikawa, O.; Konishi, H. CAN-mediated formation of furopyranones and furoquinolinones. Heterocycles 1999, 51, 2881-2892.
21. (a) Bar, G.; Parsons, A.F.; Thomas, C.B. A radical approach to araliopsine and related quinoline alkaloids using manganese(III) acetate. Tetrahedron Lett. 2000, 41, 7751-7755; (b) Bar, G.; Parsons, A.F.; Thomas, C.B. Manganese(III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids. Tetrahedron 2001, 57, 4719-4728.
22. (a) Bar, G.; Parsons, A.F.; Thomas, C.B. A radical approach to araliopsine and related quinoline alkaloids using manganese(III) acetate. Tetrahedron Lett. 2000, 41, 7751-7755; (b) Bar, G.; Parsons, A.F.; Thomas, C.B. Manganese(III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids. Tetrahedron 2001, 57, 4719-4728.
23. Lee, Y.R.; Kim, B.S.; Kweon, H.I. Efficient synthesis of dihydrofuroquinolinones and furoquinolinones by silver(I)/celite promoted oxidative cycloaddition. Tetrahedron 2000, 56, 3867-3874.
24. Yamada, T.; Iwahara, Y.; Nishino, H.; Kurosawa, K. Manganese(II) and (III)-mediated free-radical cyclisation of alkenes, β-keto esters and molecular oxygen. J. Chem. Soc., Perkin Trans. 1 1993, 609-616.
25. Ho, T-L. Cerium(IV) Ammonium Nitrate. In: Encyclopedia of Reagents for Organic Synthesis; Paquette, L.A., Ed.; Wiley: Chichester, 1995; Vol. 2, 1025-1029.
26. Nair, V.; Panicker, S.B.; Augustine, A.; George, T.G.; Thomas, S.; Vairamani, M. An efficient bromination of alkenes using cerium(IV) ammonium nitrate (CAN) and potassium bromide. Tetrahedron 2001, 57, 7417-7422.