A Novel Palladium-Catalyzed Intramolecular Redox Reaction

Organic Letters

Volumn 3, Issue 10, 2001, Pages 1495-1497

  Högenauer, Klemens ^a   Mulzer, Johann ^a  

^a Institut fur Organische Chemie   (Austria)

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ARTICLE;

EID: 0001709509     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015813m     Document Type: Article

References (17)

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2. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
3. For a review of forming α,β-unsaturated ketones, see: Buckle, D. R.; Pinto, I. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 7, p 119. An efficient method using IBX has recently been developed: Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. J. Am. Chem. Soc. 2000, 722, 7596.
4. For a review of forming α,β-unsaturated ketones, see: Buckle, D. R.; Pinto, I. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 7, p 119. An efficient method using IBX has recently been developed: Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. J. Am. Chem. Soc. 2000, 722, 7596.
5. (a) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1983, 24, 5635.
6. (b) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1983, 24, 5639.
7. (c) Minami, I.; Takahashi, K.; Shimizu, I.; Kimura, T.; Tsuji, J. Tetrahedron 1986, 42, 2971.
8. Kozikowski, A. P.; Tückmantel, W. Acc. Chem. Res. 1999, 32, 641.
9. (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844.
10. (b) Herrmann, W. A.; Böhm, V. P. W.; Reisinger, C.-P. J. Organomet. Chem. 1999, 576, 23.
11. The aromatic ortho protons of 5 showed NOE contacts to the olefinic proton and to the endocyclic allylic protons. In 6. the aromatic ortho protons only showed NOE contacts to the benzylic protons, which themselves showed an NOE contact to the olefinic proton.
12. (a) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581.
13. (b) For comprehensive intermolecular examples, see: Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360.
14. Triethylammonium formate has been used as a reducing agent for aryl Inflates: Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1986, 27, 5541.
15. (a) A similar palladium-catalyzed aryl homocoupling using 3 has recently been published: Hennings, D. D.; Iwama, T.; Rawal, V. H. Org. Lett. 1999, 1, 1205.
16. (b) For other examples, see: de Meijere, A.; Bräse, S. J. Organomet. Chem. 1999, 576, 88.
17. For a similar complex, see ref 2.