Paternó–Büchi反应

光诱导下羰基化合物和烯烃进行电环化得到多取代的氧杂环丁烷的反应。

反应机理

底物首先在光催化下得形成n,π-三线态，进而形成三线态双自由基，然后通过单线态双自由基成环。

反应实例

参考文献

1. (a) Paternó, E.; Chieffi, G. Gazz. Chim. Ital. 1909, 39, 341-􀀐361. Emaubuele Paternó (1847􀀐-1935) was born in Palermo, Sicily, Italy. It was 104 years ago when he first described photoinduced oxetane formation. 【Emaubuele Paternó (1847􀀐-1935)生于意大利西西里岛巴勒莫。他在107年前发现了光诱导氧杂环丁烷成环反应。】(b) Büchi, G.; Inman, C. G.; Lipinsky, E.S. J. Am. Chem. Soc. 1954, 76, 4327􀀐-4331. George H. Büchi (1921-􀀐1998) was born in Baden, Switzerland. He was a professor at MIT when he elucidated the structure of oxetanes, the products from the light-catalyzed addition of carbonyl compounds to olefins, which had been observed by E. Paternó in 1909. Büchi died of heart failure while hiking with his wife in his native Switzerland.【 George H. Büchi (1921-􀀐1998)生于瑞士巴登。他在出任麻省理工学院教授时，利用羰基化合物通过光催化加成到烯烃上得到了氧杂环丁烷（E. Paternó于1909年发现的反应），并证明了其结构。Büchi在其祖国瑞士远足旅行时死于心力衰竭。】

2. Koch, H.; Runsink, J.; Scharf, H.-D. Tetrahedron Lett. 1983, 24, 3217-􀀐3220.

3. Carless, H. A. J. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum Press: New York, 1984, 425. (Review).

4. Morris, T. H.; Smith, E. H.; Walsh, R. J. Chem. Soc., Chem. Commun. 1987, 964-􀀐965.

5. Porco, J. A., Jr.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol. 5, 151􀀐-192. (Review).

6. de la Torre, M. C.; Garcia, I.; Sierra, M. A. J. Org. Chem. 2003, 68, 6611-􀀐6618.

7. Griesbeck, A. G.; Mauder, H.; Stadtmüller, S. Acc. Chem. Res. 1994, 27, 70􀀐-75. (Review).

8. D’Auria, M.; Emanuele, L.; Racioppi, R. Tetrahedron Lett. 2004, 45, 3877-􀀐3880.

9. Liu, C. M. Paternó–Büchi Reaction. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2005, pp 44-􀀐49. (Review).

10. Cho, D. W.; Lee, H.-Y.; Oh, S. W.; Choi, J. H.; Park, H. J.; Mariano, P. S.; Yoon, U.C. J. Org. Chem. 2008, 73, 4539-􀀐4547.

11. D’Annibale, A.; D’Auria, M.; Prati, F.; Romagnoli, C.; Stoia, S.; Racioppi, R.;

Viggiani, L. Tetrahedron 2013, 69, 3782-􀀐3795.

编译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li,  Paternó–Büchi reaction，page 460-461.