Citation: Zhou Danni, Wang Chunxia, Li Mingliang, Long Zheng, Lan Jingbo. Palladium-catalyzed 2-pyridylmethyl-directed β-C(sp³)-H activation and cyclization of aliphatic amides with gem-dibromoolefins: A rapid access to γ-lactams[J]. Chinese Chemical Letters, ;2018, 29(1): 191-193. doi: 10.1016/j.cclet.2017.06.007 shu

Palladium-catalyzed 2-pyridylmethyl-directed β-C(sp³)-H activation and cyclization of aliphatic amides with gem-dibromoolefins: A rapid access to γ-lactams

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China

Corresponding author: Lan Jingbo, jingbolan@scu.edu.cn
Received Date: 18 April 2017
Revised Date: 26 May 2017
Accepted Date: 2 June 2017
Available Online: 4 January 2017

Figures(4)

The direct Pd-catalyzed β-C(sp³)-H activation and cyclization of aliphatic amides bearing a removable 2-pyridylmethyl directing group with gem-dibromoolefins is described for the first time to construct a variety of γ-lactams. The resulting products with Z-and E-configurations can be easily separated and purified after the reaction, demonstrating the effectiveness and applicability of the method herein developed.
- C (sp³)-H activation,
- Palladium-catalyzed,
- gem-Dibromoolefins,
- Removable directing group,
- γ-Lactams
1. [1]
  (a) R. Giri, B. F. Shi, K. M. Engle, et al., Chem. Soc. Rev. 38(2009) 3242-3272;
  (b) T. W. Lyons, M. S. Sanford, Chem. Rev. 110(2010) 1147-1169;
  (c) J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 40(2011) 4740-4761;
  (d) S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 40(2011) 5068-5083;
  (e) C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 111(2011) 1780-1824;
  (f) K. Hirano, M. Miura, Chem. Commun. 48(2012) 10704-10714;
  (g) Y. Yang, J. Lan, J. You, Chem. Rev. 117(2017), doi: http://dx.doi.org/10.1021/acs.chemrev.6b00567.
2. [2]
  (a) O. Baudoin, Chem. Soc. Rev. 40(2011) 4902-4911;
  (b) B. J. Li, Z. J. Shi, Chem. Soc. Rev. 41(2012) 5588-5598;
  (c) J. L. Jeffrey, R. Sarpong, Chem. Sci. 4(2013) 4092-4106;
  (d) J. Xie, C. Pan, A. Abdukader, C. Zhu, Chem. Soc. Rev. 43(2014) 5245-5256;
  (e) W. H. Rao, B. F. Shi, Org. Chem. Front. 3(2016) 1028-1047.
3. [3]
  (a) V. G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 127(2005) 13154-13155;
  (b) N. Hasegawa, V. Charra, S. Inoue, et al., J. Am. Chem. Soc. 133(2011) 8070-8073;
  (c) N. Rodríguez, J. A. Romero-Revilla, M. Á. Fernández-Ibáñez, J. C. Carretero, Chem. Sci. 4(2013) 175-179;
  (d) M. Zhang, Y. Zhang, X. Jie, et al., Org. Chem. Front. 1(2014) 843-895.
4. [4]
  F. Zhang, D.R. Spring, Chem. Soc. Rev. 43(2014) 6906-6919. doi: 10.1039/C4CS00137K
5. [5]
  (a) R. H. Feling, G. O. Buchanan, T. J. Mincer, et al., Angew. Chem. Int. Ed. 42(2003) 355-357;
  (b) M. Stadler, J. Bitzer, A. Mayer-Bartschmid, et al., J. Nat. Prod. 70(2007) 246-252;
  (c) T. A. M. Gulder, B. S. Moore, Angew. Chem. Int. Ed. 49(2010) 9346-9367;
  (d) J. Caruano, G. G. Muccioli, R. Robiette, Org. Biomol. Chem. 14(2016) 10134-10156.
6. [6]
  (a) S. H. Kang, H. S. Jun, Chem. Commun. (1998) 1929-1930;
  (b) E. J. Corey, W. D. Z. Li, Chem. Pharm. Bull. 47(1999) 1-10;
  (c) A. G. M. Barrett, J. Head, M. L. Smith, et al., J. Org. Chem. 64(1999) 6005-6018;
  (d) Y. Hayashi, M. Shoji, J. Yamaguchi, et al., J. Am. Chem. Soc. 124(2002) 12078-12079;
  (e) A. Yazici, S. G. Pyne, Synthesis 3(2009) 339-368;
  (f) A. Yazici, S. G. Pyne, Synthesis 3(2009) 513-541;
  (g) P. Q. Huang, H. Geng, Y. S. Tian, et al., Science China-Chem. 58(2015) 478-482;
  (h) J. L. Ye, Y. Liu, Z. P. Yang, P. Q. Huang, Chem. Commun. 52(2016) 561-563.
7. [7]
  (a) X. Wu, K. Yang, Y. Zhao, et al., Nat. Commun. 6(2015) 6462-6471;
  (b) G. He, S. Y. Zhang, W. A. Nack, et al., Angew. Chem. Int. Ed. 52(2013) 11124-11128;
  (c) J. Zhang, H. Chen, C. Lin, et al., J. Am. Chem. Soc. 137(2015) 12990-12996;
  (d) J. Zhang, D. Li, H. Chen, et al., Adv. Synth. Catal. 358(2016) 792-807.
8. [8]
  (a) S. Inoue, H. Shiota, Y. Fukumoto, N. Chatani, J. Am. Chem. Soc. 131(2009) 6898-6899;
  (b) H. Shiota, Y. Ano, Y. Aihara, et al., J. Am. Chem. Soc. 133(2011) 14952-14955.
9. [9]
  X. Huang, Y. Wang, J. Lan, J. You, Angew. Chem. Int. Ed. 54(2015) 9404-9408. doi: 10.1002/anie.201504507
10. [10]
  E.M. Simmons, J.F. Hartwig, Angew. Chem. Int. Ed. 51(2012) 3066-3072. doi: 10.1002/anie.v51.13
11. [11]
  Y. Aihara, N. Chatani, J. Am. Chem. Soc. 136(2014) 898-901. doi: 10.1021/ja411715v
12. [12]
  D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 132(2010) 3965-3972. doi: 10.1021/ja910900p
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沈阳化工大学材料科学与工程学院沈阳 110142

Palladium-catalyzed 2-pyridylmethyl-directed β-C(sp3)-H activation and cyclization of aliphatic amides with gem-dibromoolefins: A rapid access to γ-lactams

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通讯作者: 陈斌, bchen63@163.com

Palladium-catalyzed 2-pyridylmethyl-directed β-C(sp³)-H activation and cyclization of aliphatic amides with gem-dibromoolefins: A rapid access to γ-lactams