Barton自由基脱羧反应

羧酸转化为Barton酯,然后进行自由基脱羧的反应。

反应机理

反应实例

此反应中没有加入氢化锡,而是生成硫醚中间体,然后消除。

参考文献

  1. Barton, D. H. R.; Crich, D.; Motherwell, W. B. J. Chem. Soc., Chem. Commun. 1983,939-941. Sir Derek Barton (United Kingdom, 1918-1998) studied under Ian Heilbron at Imperial College in his youth. He taught in England, France and the US. Barton won the Nobel Prize in Chemistry in 1969 for development of the concept of conformation. He passed away in his office at the University of Texas A&M in 1998.  Derek Barton先生(英国化学家,1918-1998),年轻时在伦敦帝国理工学院学习,师从 Ian Heilbron。后来又在英国,法国和美国教学。他由于在有机化学构象方面的研究获得了1969年的诺贝尔化学奖。他于1998年德克萨斯A&M大学的办公室内去世。

  2. Barton, D. H. R.; Zard, S. Z. Pure Appl. Chem. 1986, 58, 675-684. (Review).

  3. Cochane, E. J.; Lazer, S. W.; Pinhey, J. T.; Whitby, J. D. Tetrahedron Lett. 1989, 30, 7111-7114.

  4. Barton, D. H. R. Aldrichimica Acta 1990, 23, 3. (Review).

  5. Crich, D.; Hwang, J.-T.; Yuan, H. J. Org. Chem. 1996, 61, 6189-6198.

  6. Yamaguchi, K.; Kazuta, Y.; Abe, H.; Matsuda, A.; Shuto, S. J. Org. Chem. 2003, 68, 9255-9262.

  7. Zard, S. Z. Radical Reactions in Organic Synthesis Oxford University Press: Oxford, UK, 2003. (Book).

  8. Carry, J.-C.; Evers, M.; Barriere, J.-C.; Bashiardes, G.; Bensoussan, C.; Gueguen, J.-C.; Dereu, N.; Filoche, B.; Sable, S.; Vuilhorgne, M.; Mignani, S. Synlett 2004, 316-320.

  9. Brault, L.; Denance, M.; Banaszak, E.; El Maadidi, S.; Battaglia, E.; Bagrel, D.; Samadi, M. Eur. J. Med. Chem. 2007, 42, 243-247.

  10. Guthrie, D. B.; Curran, D. P. Org. Lett. 2009, 11, 249-251.

  11. He, Z.; Trinchera, P.; Adachi, S.; St. Denis, J. D.; Yudin, A. K. Angew. Chem. Int. Ed. 2012, 51, 11092–11096.

编译自:J.J. Li, Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications,  Barton radical decarboxylation,page 26-27.

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