Chinese Journal of Organic Chemistry >
Palladium-Catalyzed Regioselective Aryl Phenoxylation of Allenamide
Received date: 2023-09-04
Revised date: 2023-09-12
Online published: 2024-01-31
Supported by
National Natural Science Foundation of China(22078178)
A palladium-catalyzed regioselective aryl phenoxylation of allenamide with phenol derivatives has been developed, providing valuable branched allyl ether products in moderate to excellent yields under mild reaction conditions. Importantly, only the proximal addition products of allenamide were observed in the reaction process, and no distal addition products were observed. A coordinated palladium complex was proposed to be responsible for the excellent proximal addition in the insertion step. The final nucleophilic attack at α-position was induced by the steric effect of palladium complex.
Key words: palladium-catalysis; proximal addition; aryl phenoxylation
Xianqiang Meng , Yi Yang , Wanjie Liang , Jingtao Wang , Rongkui Zhang , Hui Liu . Palladium-Catalyzed Regioselective Aryl Phenoxylation of Allenamide[J]. Chinese Journal of Organic Chemistry, 2024 , 44(1) : 224 -231 . DOI: 10.6023/cjoc202309003
| [1] | (a) Wei, Y.; Shi, M. Org. Chem. Front. 2017, 4, 1876. |
| [1] | (b) Pulis, A. P.; Yeung, K. D.; Procter, J. Chem. Sci. 2017, 8, 5240. |
| [1] | (c) Alonso, J. M.; Quiros, M. T.; Munoz, M. P. Org. Chem. Front. 2016, 3, 1186. |
| [1] | (d) Koschker, P.; Breit, B. Acc. Chem. Res. 2016, 49, 1524. |
| [1] | (e) Ye, J.; Ma, S. Org. Chem. Front. 2014, 1, 1210. |
| [1] | (f) Yang, W.; Hashmi, A. S. K. Chem. Soc. Rev. 2014, 43, 2941. |
| [1] | (g) Wang, Z.; Xu, X.; Kwon, O. Chem. Soc. Rev. 2014, 43, 2927. |
| [1] | (h) Yu, S.; Ma, S. Angew. Chem., Int. Ed. 2012, 51, 3074. |
| [1] | (i) Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994. |
| [1] | (j) Ma, S. Acc. Chem. Res. 2009, 42, 1679. |
| [1] | (k) Jeganmohan, M.; Cheng, C. H. Chem.-Eur. J. 2008, 14, 10876. |
| [1] | (l) Bravo-Altamirano, K.; Abrunhosa-Thomas, I.; Montchamp, J. L. J. Org. Chem. 2008, 73, 2292. |
| [1] | (m) Ma, S. Chem. Rev. 2005, 105, 2829. |
| [1] | (n) Ma, S. Acc. Chem. Res. 2003, 36, 701. |
| [1] | (o) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. |
| [1] | (p) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535. |
| [2] | (a) Liu, Z.; Breit, B. Angew. Chem., Int. Ed. 2016, 128, 8580. |
| [2] | (b) McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981. |
| [3] | (a) Guo, X.; Nelson, A. K.; Slebodnick, C.; Santos, W. L. ACS Catal. 2015, 5, 2172. |
| [3] | (b) Yang, F. Y.; Cheng, C. H. J. Am. Chem. Soc. 2001, 123, 761. |
| [3] | (c) Ishiyama, T.; Kitano, T.; Miyaura, N. Tetrahedron Lett. 1998, 39, 2357. |
| [3] | (d) Burks, H. E.; Liu, S.; Morken, J. P.; J. Am. Chem. Soc. 2007, 129, 8766. |
| [3] | (e) Pelz, N. F.; Woodward, A. R.; Burks, H. E.; Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2004, 126, 16328. |
| [4] | Chang, K. J.; Rayabarapu, D. K.; Yang, F. Y.; Cheng, C. H. J. Am. Chem. Soc. 2005, 127, 126. |
| [5] | (a) Truce, W. E.; Heuring, D. L.; Wolf, G. C. J. Org. Chem. 1974, 39, 238. |
| [5] | (b) Kang, S. K.; Seo, H. W.; Ha, Y. H. Synthesis 2001, 2001, 1321. |
| [5] | (c) Lu, N.; Zhang, Z.; Ma, N.; Wu, C.; Zhang, G.; Liu, Q.; Liu, T. Org. Lett. 2018, 20, 4318. |
| [6] | Zhang, G.; Xiong, T.; Wang, Z.; Xu, G.; Wang, X.; Zhang, Q. Angew. Chem., Int. Ed. 2015, 54, 12649. |
| [7] | Hu, J.; Xie, Y.; Huang, H. Angew. Chem., Int. Ed. 2014, 53, 7272. |
| [8] | (a) Yu, L.; Ren, L.; Guo, R.; Chen, T. Synth. Commun. 2011, 41, 1958. |
| [8] | (b) Kamiya, I.; Nishinaka, E.; Ogawa, A. Tetrahedron Lett. 2005, 46, 3649. |
| [8] | (c) Kodama, S.; Nishinaka, E.; Nomoto, A.; Sonoda, M.; Ogawa, A. Tetrahedron Lett. 2007, 48, 6312. |
| [8] | (d) Kippo, T.; Fukuyama, T.; Ryu, I. Org. Lett. 2011, 13, 3864. |
| [8] | (e) Hirata, Y.; Inui, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 2009, 131, 6624. |
| [8] | (f) Hua, R.; Tanaka, M. Tetrahedron Lett. 2004, 45, 2367. |
| [8] | (g) Toyofuku, M.; Murase, E.; Fujiwara, S.; Shinike, T.; Kuniyasu, H.; Kambe, N. Org. Lett. 2008, 10, 3957. |
| [8] | (h) Nakao, Y.; Shirakawa, E.; Tsuchimoto, T.; Hiyama, T. J. Org. Chem. 2004, 689, 3701. |
| [8] | (i) Xia, X.; Wang, Y.; Zhang, L.; Song, X.; Liu, X.; Liang, Y. Chem.-Eur. J. 2014, 20, 5087. |
| [8] | (j) Wang, H.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 7318. |
| [8] | (k) Miura, T.; Yamauchi, M.; Kosaka, A.; Murakami, M. Angew. Chem., Int. Ed. 2010, 49, 4955. |
| [8] | (l) Kang, Y.; Kice, J. Tetrahedron Lett. 1982, 23, 5373. |
| [8] | (m) Yang, Y.; Wang, H.; Sun, Z.; Li, X.; Sun, F.; Liu, Q.; Liu, H. Org. Chem. Front. 2022, 9, 5969. |
| [9] | (a) Blieck, R.; Taillefer, M.; Monnier, F. Chem. Rev. 2020, 120, 13545. |
| [9] | (b) Enthaler, S. Chem. Soc. Rev. 2011, 40, 4912. |
| [9] | (c) Li, G.; Huo, X.; Jiang, X. Chem. Soc. Rev. 2020, 49, 2060. |
| [9] | (d) Kawamoto, T.; Hirabayashi, S.; Guo, X. Chem. Commun. 2009, 24, 3528. |
| [9] | (e) Liu, Z.; Breit, B. Org. Lett. 2018, 20, 300. |
| [10] | Okuro, K.; Alper, H. J. Org. Chem. 1997, 62, 1566. |
| [11] | Nishina, N.; Yamamoto, Y. Tetrahedron Lett. 2008, 49, 4908. |
| [12] | Oguri, H.; Tanaka, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 2000, 41, 975. |
| [13] | Oguri, H. Bull. Chem. Soc. Jpn. 2007, 80, 1870. |
| [14] | Donnard, M.; Tschamber, T.; Desrat, S.; Hinsinger, K.; Eustache, J. Tetrahedron Lett. 2008, 49, 1192. |
| [15] | Jiang, L.; Jia, T.; Wang, M.; Liao, J.; Cao, P. Org. Lett. 2015, 17, 1070. |
| [16] | Alam, K.; Li, T.; Hyatt, I. D.; Croatt, M. P. Org. Biomol. Chem. 2022, 20, 4719. |
| [17] | Yang, Y.; Wang, H.; Sun, Z.; Li, X.; Sun, F.; Liu, Q.; Zhang, L.; Xu, L.; Liu, H. Org. Chem. Front. 2022, 9, 5969. |
| [18] | (a) Suárez-Pantiga, S.; Hernández-Díaz, C.; Piedrafita, M.; Rubio, E.; González, J. M. Adv. Synth. Catal. 2012, 354, 1651. |
| [18] | (b) Ballesteros, A.; Morán-Poladura, P.; González, J. M. Chem. Commun. 2016, 52, 2905. |
| [18] | (c) Cui, J.; Meng, L.; Chi, X.; Liu, Q.; Zhao, P.; Zhang, D.; Chen, L.; Li, X.; Dong, Y.; Liu, H. Chem. Commun. 2019, 55, 4355. |
| [18] | (d) Du, X.; Zhao, H.; Li, X.; Zhang, L.; Dong, Y.; Wang, P.; Zhang, D.; Liu, Q.; Liu, H. J. Org. Chem. 2021, 86, 13276. |
/
| 〈 |
|
〉 |