Parham环化反应

烷基锂和芳基卤代物进行交换得到芳基锂,然后进行分子内的亲核加成得到关环产物的反应。

反应机理

为啥要两个当量?

反应实例

参考文献

1. (a) Parham, W. E.; Jones, L. D.; Sayed, Y. J. Org. Chem. 1975, 40, 2394-􀀐2399. William E. Parham was a professor at Duke University. (b) Parham, W. E.; Jones, L. D.; Sayed, Y. J. Org. Chem. 1976, 41, 1184-􀀐1186. (c) Parham, W. E.; Bradsher, C. K. Acc. Chem. Res. 1982, 15, 300􀀐-305. (Review).

2. Paleo, M. R.; Lamas, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1992, 57, 2029–2033.

3. Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Exeter, 1995; Vol. 11; p66. (Review).

4. Gauthier, D. R., Jr.; Bender, S. L. Tetrahedron Lett. 1996, 37, 13–16.

5. Collado, M. I.; Manteca, I.; Sotomayor, N.; Villa, M.-J.; Lete, E. J. Org. Chem. 1997, 62, 2080-􀀐2092.

6. Mealy, M. M.; Bailey, W. F. J. Organomet. Chem. 2002, 646, 59-􀀐67. (Review).

7. Sotomayor, N.; Lete, E. Current Org. Chem. 2003, 7, 275-􀀐300. (Review).

8. González-Temprano, I.; Osante, I.; Lete, E.; Sotomayor, N. J. Org. Chem. 2004, 69,3875􀀐-3885.

9. Moreau, A.; Couture, A.; Deniau, E.; Grandclaudon, P.; Lebrun, S. Org. Biomol.Chem. 2005, 3, 2305􀀐-2309.

10. Gribble, G. W. Parham cyclization. In Name Reactions for Homologations-Part II; Li,J. J., Ed.; Wiley: Hoboken, NJ, 2009, pp 749􀀐-764. (Review).

11. Aranzamendi, E.; Sotomayor, N.; Lete, E. J. Org. Chem. 2012, 77, 2986-􀀐2991.

12. Huard, K.; Bagley, S. W.; Menhaji-Klotz, E.; et al. J. Org. Chem. 2012, 77,

10050-10057.

编译自:J.J. Li, Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications, Parham cyclizationpage 456-457.

(0)

相关推荐