Miyaura硼酸化反应

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钯催化下芳基卤代物和双联硼试剂反应制备芳基硼酸酯的反应。也被称为Hosomi-Miyaura硼酸化反应。

反应机理


机理分为芳基卤代物的氧化加成，金属转移和还原消除三步。



反应实例



一锅法制备双吲哚化合物。

参考文献

1. Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508-7510.

2. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (Review).

3. Suzuki, A. J. Organomet. Chem. 1995, 576, 147-168. (Review).

4. Carbonnelle, A.-C.; Zhu, J. Org. Lett. 2000, 2, 3477-3480.

5. Giroux, A. Tetrahedron Lett. 2003, 44, 233-235.

6. Kabalka, G. W.; Yao, M.-L. Tetrahedron Lett. 2003, 44, 7885-7887.

7. Ramachandran, P. V.; Pratihar, D.; Biswas, D.; Srivastava, A.; Reddy, M. V. R. Org.Lett. 2004, 6, 481-484.

8. Occhiato, E. G.; Lo Galbo, F.; Guarna, A. J. Org. Chem. 2005, 70, 7324-7330.

9. Skaff, O.; Jolliffe, K. A.; Hutton, C. A. J. Org. Chem. 2005, 70, 7353-7363.

10. Duong, H. A.; Chua, S.; Huleatt, P. B.; Chai, C. L. L. J. Org. Chem. 2008, 73,

9177-9180.

11. Jo, T. S.; Kim, S. H.; Shin, J.; Bae, C. J. Am. Chem. Soc. 2009, 131, 1656-1657.

12. Marciasini, L. D.; Richy, N.; Vaultier, M.; Pucheault, M. Adv. Synth. Cat. 2013, 355, 1083–1088.


译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Miyaura borylation，page 409-410.


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