Palladium/Phosphine Complex-Catalyzed (4 + 4) Annulations of Morita-Baylis-Hillman Carbonates and 1-Azadienes

doi:10.6023/cjoc202405020

Chinese Journal of Organic Chemistry

ARTICLE

钯/膦配合物催化Morita-Baylis-Hillman碳酸酯与氮杂二烯的(4 + 4)环化反应

朱波, 杨杨, 刘淇尹, 杜玮^*, 陈应春^*

四川大学华西药学院成都 610041

收稿日期:2024-05-15 修回日期:2024-06-21
基金资助:
国家自然科学基金(No. 21971166)资助项目.

Palladium/Phosphine Complex-Catalyzed (4 + 4) Annulations of Morita-Baylis-Hillman Carbonates and 1-Azadienes

Zhu Bo, Yang Yang, Liu Qiyin, Du Wei^*, Chen Yingchun^*

West China School of Pharmacy, Sichuan University, Chengdu, 610041

Received:2024-05-15 Revised:2024-06-21
Contact: *E-mail: ycchen@scu.edu.cn
Supported by:
National Natural Science Foundation of China (No. 21971166).

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Abstract

Here we report a (4 + 4) annulation reaction for the construction of medium-sized N-heterocycles. This process involves the generation of all-carbon 1,4-dipoles containing a π-allylpalladium complex from Morita-Baylis-Hillman (MBH) carbonates under the catalysis of Pd/Synphos, which then undergo Michael addition/N-allylic alkylation with 1-azadienes. A spectrum of eight-membered N-heterocycles featuring a trisubstituted exo-cyclic double bond are furnished efficiently, with moderate to good E/Z selectivity and moderate atroposelectivity. In addition, moderate enantioselectivity can be realized by using a chiral ligand or with the assistant of a chiral quaternary ammonium salt.

Key words: palladium/phosphine complex, Morita-Baylis-Hillman carbonates, all-carbon 1,4-dipoles, (4 + 4) annulation, eight-membered N-heterocycles

Cite this article

Zhu Bo, Yang Yang, Liu Qiyin, Du Wei, Chen Yingchun. Palladium/Phosphine Complex-Catalyzed (4 + 4) Annulations of Morita-Baylis-Hillman Carbonates and 1-Azadienes[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202405020.

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[1] (a) Laakso, J. A.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Org. Chem. 1992, 57, 2066.
(b) Lee, S.; Sperry, J. Bioorg. Med. Chem. 2022, 54, 116560.
(c) Toma, T.; Kita, Y.; Fukuyama, T. J. Am. Chem. Soc. 2010, 132, 10233.
(d) Qin, H.; Xu, Z.; Cui, Y.; Jia, Y. Angew. Chem., Int. Ed. 2011, 50, 4447.
(e) Miloserdov, F. M.; Kirillova, M. S.; Muratore, M. E.; Echavarren, A. M. J. Am. Chem. Soc. 2018, 140, 5393.
[2] (a) Reyes, R. L.; Iwai, T.; Sawamura, M. Chem. Rev. 2021, 121, 8926.
(b) Wang, Y.-H.; Jin, Z.-F.; Zhou, L.J.; Lv, X. Org. Biomol. Chem. 2024, 22, 252.
(c) Li, J.; Dong, Z.-Y.; Zhao, C.-G. New. J. Chem. 2024, 48, 4645.
[3] (a) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
(b) Molander, G.-A. Acc. Chem. Res. 1998, 31, 603.
[4] (a) Zhang, M.-M.; Qu, B.-L.; Shi, B.; Xiao, W.-J.; Lu, L.-Q. Chem. Soc. Rev. 2022, 51, 4146.
(b) Wang, B.-C.; Wei, Y.; Xiong, F.-Y.; Qu, B.-L.; Xiao, W.-J.; Lu, L.-Q. Sci. China Chem. 2022, 65, 2437.
(c) Shi, L.; Xiong, Q.; Wu, S.-Y.; Li, Y.; Shen, P.; Lu, J.; Ran, G.-Y. Org. Lett. 2023, 25, 2030.
(d) Wang, L.; Yang, S.; Tang, Y.; Li, K.; Lu, M.-X.; Guo, H.-C. J. Org. Chem. 2024, 89, 5019.
[5] (a) Li, Q.-Y.; Pan, R.; Wang, M.-H.; Yao, H.-Q.; Lin, A.-J. Org. Lett. 2021, 23, 2292.
(b) Scuiller, A.; Liu, X.-Y.; Cordier, M.; Garrec, J.; Archambeau, A. Synlett 2021, 32, 981.
(c) Song, Q.; Liu, Y.; Cai, L.-L.; Cao, X.-Y.; Qian, S.; Wang, Z.-Y. Chin. Chem. Lett. 2022, 33, 4549.
(d) Meng, Y.-G.; Wang, Q.; Yao, X.-Y.; Wei, D. H.; Liu, Y.-G.; Li, E.-Q.; Duan, Z. Org. Lett. 2022, 24, 9205.
(e) Chen, G.-H.; Ye, Y.; Zhang, D.-X.; Li, H.-G.; Zhang, N.; Liang, G.-J.; Zhang, D.; Zhou, J.; Zhou, H. Org. Chem. Front. 2023, 10, 4698.
(f) Xie, H.-L.; Chen, L.; Han, Z.-Y.; Yang, Z.-K.; Sun, J.-W.; Huang, H. Org. Lett. 2023, 25, 5011.
(g) Yuan, C.-H.; Wu, Y.; Wang, D.-Q.; Zhang, Z.-H.; Wang, C.; Zhou, L.-J.; Zhang, C.; Song, B.-A.; Guo, H.-C. Adv. Synth. Catal. 2018, 360, 652.
(h) Niu, B.; Wu, X.-Y.; Wei, Y.; Shi, M. Org. Lett. 2019, 21, 4859.
(i) Yang, W.-L.; Wang, Y.-L.; Li, W.; Gu, B.-M.; Wang, S.-W.; Luo, X.-Y.; Tian, B.-X.; Deng, W.-P. ACS. Catal. 2021, 11, 12557.
(j) Xu, H.-B.; Ma, S.-M. Angew. Chem., Int. Ed. 2023, 62, e202213676.
[6] Gao C.; Wang H.-H.; Liu J.-T.; Li X.-X. ACS Catal. 2021, 11, 2684.
[7] Gao Y.-F.; Wang H.; Chen X.-Q.; Qiao Y.-Y.; Miao Z.-Y.J. Org. Chem. 2023, 88, 11822.
[8] (a) Chen, Y.; Zang, M.; Wang, W.-J.; Liu, Y.-Z.; Luo, X.-Y.; Deng, W.-P. Chin. J. Chem. 2023, 41, 2825.
(b) Chen, G.-H.; Ye, Y.; Zhang, D.-X.; Li, H.-J.; Zhang, N.; Liang, G.-J.; Zhang, D.; Zhou, J.; Zhou, H. Org. Chem. Front. 2023, 10, 4698.
[9] Yang Y.; Zhu B.; Zhu L.; Jiang Y.; Guo C.-L.; Gu J.; Ouyang Q.; Du W.; Chen Y.-C. Chem. Sci. 2021, 12, 11399.
[10] (a) Lin, W.; Zhang, C.; Xu, W.; Cheng, Y.-Y.; Li, P.-F.; Li, W.-J. Adv. Synth. Catal. 2019, 361, 476.
(b) Hu, D.; Gao, Y.; Song, X.; Du, W.; Chen, Y.-C. Eur. J. Org. Chem. 2020, 514.
(c) Jiang, B.; Du, W.; Chen, Y.-C. Chem. Commun. 2020, 56, 7257.
(d) Yan, J.-Z.; Li, X.-P.; Chen, Y.-Z.; Li, Y.; Chen, W.-W.; Zhan, R.-T.; Huang, H.-C. J. Org. Chem. 2020, 85, 12175.
(e) Wang, C.-J. Yang, Q.-Q.; Wang, M.-X.; Shang, Y.-H.; Tong, X.-H.; Deng, Y.-H.; Shao, Z.-H. Org. Chem. Front. 2020, 7, 609.
(f) Yang, X.-X.; Yan, R.-J.; Ran, G.-Y.; Chen, C.; Yue, J.-F.; Yan, X.; Ouyang, Q.; Du, W.; Chen, Y.-C. Angew. Chem. Int. Ed. 2021, 60, 26762
(g) Luo, Q.-Q.; Tian, Z.; Tang, J.; Wang, J.; Tian, Y.; Peng, C.; Zhan, G.; Han, B. ACS Catal. 2022, 12, 7221.
(h) Yang T.; Jiang Q.; Wang C.-M.; Li S.-L.; He C.-Y.; Chu W.-D.; Liu Q.-Z. Org. Lett.2023, 25, 13, 2243.
[11] (a) Tabata, H.; Wada, N.; Takada, Y.; Oshitari, T.; Takahashi, H.; Natsugari, H. J. Org. Chem. 2011, 76, 5123.
(b) Wang, L.; Li, S.; Marcus.; Arne R. P.; Wang, A.; Rakesh P.; Kari, R.; Dieter, E. Angew. Chem., Int. Ed. 2016, 128, 11276.
[12] For more details, see the Supporting Information.
[13] (a) Xie, P.-Z.; Huang, Y. Org. Biomol. Chem. 2015, 13, 8578.
(b) Liu, T.-Y.; Xie, M.; Chen, Y.-C. Chem. Soc. Rev. 2012, 41, 4101.
[14] (a) Ohmatsu, K.; Imagawa, N.; Ooi, T. Nat. Chem. 2014, 6, 47.
(b) Ohmatsu, K.; Kawai, S.; Imagawa, N.; Ooi, T. ACS Catal. 2014, 4, 4304.
[15] Deposition numbers 2355492 (E-3a) and 2355493 (Z-3a) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre.

钯/膦配合物催化Morita-Baylis-Hillman碳酸酯与氮杂二烯的(4 + 4)环化反应

Palladium/Phosphine Complex-Catalyzed (4 + 4) Annulations of Morita-Baylis-Hillman Carbonates and 1-Azadienes

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