TEMPO-mediated environmentally benign oxidation of primary alcohols to carboxylic acids with poly[4-(diacetoxyiodo)styrene]

Synlett

Volumn , Issue 11, 2004, Pages 2010-2012

  Tashino, Yousuke ^a   Togo, Hideo ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Alcohol; Aldehyde; Carboxylic acid; Environmentally benign; Oxidation; Poly 4 (diacetoxyiodo) styrene ; TEMPO

Indexed keywords

2,2,6,6 TETRAMETHYLPIPERIDINE 1 OXYL; ACETONE; ALCOHOL; CARBOXYLIC ACID DERIVATIVE; PIPERIDINE DERIVATIVE; POLY[4 (DIACETOXYIODO)STYRENE]; POLYSTYRENE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; COLUMN CHROMATOGRAPHY; OXIDATION;

EID: 4544383431     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-830881     Document Type: Article

References (34)

1. Hudlicky, M. Oxidations in Organic Chemistry; American Chemical Society: Washington D.C., 1990.
2. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
3. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
4. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
5. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
6. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
7. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
8. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
9. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
10. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
11. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
12. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
13. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
14. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
15. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
16. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
17. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
18. TEMPO-mediated oxidation of alcohols. Reviews: (a) Bobbitt, J. M.; Flores, C. L. Heterocycles 1988, 27, 509. (b) Yamaguchi, M.; Miyazawa, T.; Takata, T.; Endo, T. Pure Appl. Chem. 1990, 62, 217. (c) de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153; and references are cited therein. (d) Recent reports: Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (e) Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029. (f) Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310. (g) Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. (h) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (j) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999. (k) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285. (l) Oxidation of alcohols with polymer-supported TEMPO: Heeres, A.; van Doren, H. R.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221. (m) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795. (n) Dijksman, A.; Arenas, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271. (o) Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Angew. Chem. Int. Ed. 2001, 40, 1436. (p) Tanyeli, C.; Gümüs, A. Tetrahedron Lett. 2003, 44, 1639. (q) Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
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34. Carboxylic acids were identified by comparison with commercially available authentic materials.