F. Alonso et al. / Tetrahedron 56 (2000) 8673±8678
8677
Methoden der Organischen Chemie (Houben-Weyl) 1980, 4 (1c),
482. (d) Rylander, P. N. In Hydrogenation Methods; Academic:
London, 1985; p. 168.
spectroscopic analyses by comparison with commercially
available samples.
12. See, for instance: (a) Zhang, Y.; Lin, R. Synth. Commun. 1987,
17, 329±332. (b) Kambe, N.; Kondo, K.; Sonoda, N. Angew.
Chem. 1980, 92, 1042±1043. (c) Akiba, M.; Cava, M. P. Synth.
Commun. 1984, 14, 1119±1127. (d) Kijima, M.; Nambu, Y.; Endo,
T.; Okawara, M. J. Org. Chem. 1983, 48, 2407±2409. (e) Park,
K. K.; Han, S. Y. Tetrahedron Lett. 1996, 37, 6721±6724. (f) Patil,
M. L.; Jnaneschwara, G. K..; Sabde, D. P.; Dongare, M. K.;
Sudalai, A.; Deshpande, V. H. Tetrahedron Lett. 1997, 38,
2137±2140.
4-Vinylbiphenyl-divinylbenzene
copolymer
(20 mg,
0.1 mmol) was used as an alternative electron transfer
agent instead of DTBB to perform the reactions in Table 1
(entry 4 and footnote c), Table 2 (entries 1 and 7, and
footnote c), and Table 3 (entry 4 and footnote d).
Acknowledgements
13. For electrochemical13a or photochemical13b procedures see,
for instance: (a) Bracht, J. Methoden der Organischen Chemie
(Houben-Weyl) 1981, 4 (1d), 575. (b) Adam, W.; Moorthy, J. N.;
Nau, W. M.; Scaiamo, J. C. J. Am. Chem. Soc. 1997, 119, 6749±
6756.
Â
This work was generously supported by the Direccion
General de EnsenÄanza Superior (DGES) of the Spanish
Â
Ministerio de Educacion y Cultura (MEC; grant no. PB97-
0133). G. R. thanks the CONICET (Buenos Aires,
Â
Argentina) for a fellowship. We thank Dr C. Gomez for
14. Gilchrist, T. L. In Comprehensive Organic Synthesis; Trost,
B. M., Fleming. I., Eds.; Pergamon: Oxford, 1991; Vol. 8, p. 390.
15. See, for instance: (a) LuÈttke, W.; Schabacker, V. Justus
Liebigs Ann. Chem. 1965, 687, 236±240. (b) Nakadate, M.;
Sueyoshi, S.; Suzuki, I. Chem. Pharm. Bull. 1970, 18, 1211±
1218. (c) Belot, G.; Degrand, C. Tetrahedron Lett. 1976, 153±154.
16. See, for instance: (a) King, R. B.; Harmon, C. A. J.
Organomet. Chem. 1975, 86, 139±141. (b) Alper, H..; Gopal, M.
J. Org. Chem. 1981, 46, 2593±2594. (c) Alper, H.; Edward, J. T.
Can. J. Chem. 1970, 48, 1543±1549. (d) Joshua, C. P.; Ramdas,
providing us a sample of vinylbiphenyl-divinylbenzene
copolymer.4
References
Â
1. For a monograph, see: Hudlicky, M., Reductions in Organic
Chemistry; 2nd ed.; ACS: Washington DC, 1996.
Â
2. (a) First account: Yus, M.; Ramon, D. J. J. Chem. Soc., Chem.
Commun. 1991, 398±400. (b) Previous paper on this topic from our
laboratory: Lorenzo, E.; Alonso, F.; Yus, M. Tetrahedron 2000, 56,
1745±1757.
Â
P. K. Synthesis 1974, 873±874. (e) Sanchez, R.; Vest, G.; Scott,
W.; Engel, P. S. J. Org. Chem. 1989, 54, 4026±4027. (f) Hortmann,
A. G.; Koo, J.; Yu, C.-C. J. Org. Chem. 1978, 43, 2289±2291.
17. He, Y.; Zhao, H.; Pan, X.; Wang, S. Synth. Commun. 1989, 19,
3047±3050.
3. For reviews, see: (a) Yus, M. Chem. Soc. Rev. 1996, 155±161.
Â
(b) Ramon, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225±237.
Â
4. For a polymer-supported version of the reaction, see: (a) Gomez,
Â
18. For reviews, see: (a) For a monograph, see: Hudlicku, M.,
Â
C.; Ruõz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397±1400.
Reductions in Organic Chemistry, 2nd ed.; ACS: Washington
DC, 1996, p. 131. (b) Gilchrist, T. L. In Comprehensive Organic
Synthesis; Trost, B. M., Fleming. I., Eds.; Pergamon: Oxford,
1991; Vol. 8, pp. 390±392. (c) Albini, A., Pietra, S. Heterocyclic
N-Oxides; CRC: Boca Raton, FL, 1991.
Â
(b) Gomez, C.; Ruõz, S.; Yus, M. Tetrahedron 1999, 55, 7017±
Â
7026.
5. (a) Alonso, F.; Yus, M. Tetrahedron Lett. 1996, 37, 6925±6928.
(b) Alonso, F.; Yus, M. Tetrahedron Lett. 1997, 38, 149±152.
(c) Alonso, F.; Yus, M. Tetrahedron 1998, 54, 1921±1928.
(d) Alonso, F.; Radivoy, G.; Yus, M. Tetrahedron 1999, 55,
4441±4444. (e) Radivoy, G.; Alonso, F.; Yus, M. Tetrahedron
1999, 55, 14479±14490.
19. See, for instance: Taylor, E. C.; Crovetti, A. J.; Boyer, N. E.
J. Am. Chem. Soc. 1957, 79, 3549±3552. (b) Berson, J. A..; Cohen,
T. J. Org. Chem. 1955, 20, 1461±1468.
20. See, for instance: (a) den Hertog, J.; Overhoff, J. Recl. Trav.
Chim. Pays-Bas 1950, 69, 468±473. (b) McCall, J. M.; Ten Brink,
R. E. Synthesis 1975, 335±336. (c) McMurry, J. E.; Kees, K. L.
J. Org. Chem. 1977, 42, 2655±2656. (d) Akita, Y.; Misu, K.;
Watanabe, T.; Otha A. Chem. Pharm. Bull. 1976, 24, 1839±
1841. (e) Sim, T. B.; Ahn, J. H.; Yoon, N. M. Synthesis 1996,
324±326. (f) Chary, K. P.; Mohan, G. H..; Iyengar, D. S. Chem.
Lett. 1999, 1339±1340. (g) Dutta, D. K.; Konwar, D. J. Chem. Res.,
Synop. 1998, 266±267. (h) Balicki, R. Synthesis 1989, 645±646.
21. Brown, H. C.; Subba Rao, B. C. J. Am. Chem. Soc. 1956, 78,
2582±2588.
6. Gilchrist, T. L. In Comprehensive Organic Synthesis, Trost,
B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; 8, pp 388±389.
7. (a) Guither, W. D.; Clark, D. G.; Castle, R. N. J. Heterocycl.
Chem. 1965, 2, 67±71. (b) Alexakis, A.; Lensen, N.; Mangeney, P.
Tetrahedron Lett. 1991, 32, 1171±1174. (c) Alexakis, A.; Lensen,
N.; Mangeney, P. Synlett 1991, 625±626.
8. (a) Mallor, I. M.; Smith, N. M. J. Chem. Soc., Perkin Trans 1
1984, 2927±2931. (b) Denmark, S. E.; Nicaise, O.; Edwards, J. P.
J. Org. Chem. 1990, 55, 6219±6223.
9. For the use of samarium diiodide for this reaction, see: (a) Burk,
M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266±6267.
(b) Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121,
6942±6943.
22. Jankovsky, M.; Ferles, M. Collect. Czech. Chem. Commun.
1970, 35, 2802±2809.
10. For reviews, see: (a) Newbold, B. T. In The Chemistry of the
Hydrazo, Azo, and Azoxy Groups; Patai, S., Ed.; Wiley: New York,
1975. (b) Gilchrist, T. L. In Comprehensive Organic Synthesis;
Trost, B. M., Fleming. I., Eds.; Pergamon: Oxford, 1991; Vol. 8,
p. 382. (c) Sandler, S. R., Karo, W. In Organic Functional Group
Preparations; Academic: Orlando, 1983; Vol. 1, p. 452.
Â
11. (a) Hajos, A. Methoden der Organischen Chemie (Houben-
Weyl) 1980, 4 (1d), 1. (b) Pratt, J. M.; Swinden, G. J. Chem.
Soc., Chem. Commun. 1969, 1321±1322. (c) Lehmann, J.
23. For other methods including phosphorous, sulfur and selenium
compounds see, for instance: (a) Emerson, T. R.; Rees, C. W.
J. Chem. Soc. 1962, 1917±1923. (b) Howard, E.; Olszewski, W.
F. J. Am. Chem. Soc. 1959, 81, 1483±1484. (c) Bonini, B. F.;
Maccagnani, G.; Mazzanti, G.; Pedrini, P. Tetrahedron Lett.
1979, 20, 1799±1800. (d) Olah, G. A.; Arvanaghi, M.; Vankar,
Y. D. Synthesis 1980, 660±661. (e) Morita, T.; Kuroda, K.;
Okamoto, Y.; Sakurai, H. Chem. Lett. 1981, 921±924.
24. Pratt, E. F.; Govern, T. P. J. Org. Chem. 1964, 29, 1540±1543.