Nickel-Catalyzed Intramolecular Dearomative Arylation of Pyridiniums and Quinoliniums

doi:10.6023/cjoc202302016

Abstract

A nickel-catalyzed intramolecular dearomative arylation reaction of pyridiniums and quinoliniums is developed. In the presence of zinc powder as a reducing agent, the intramolecular Grignard-type addition of arylbromides to the C=N bonds of pyridiniums and quinoliniums proceeds smoothly to render pyridines and quinolines dearomatization, leading to a range of spirooxindole derivatives bearing dihydropyridine and dihydroquinoline moieties in moderate to good yields.

Key words: pyridine, quinoline, arylation, dearomatization, nickel

Cite this article

Jun Lu, Qichuang Li, Renxiao Liang, Yixia Jia. Nickel-Catalyzed Intramolecular Dearomative Arylation of Pyridiniums and Quinoliniums[J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1875-1882.

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References 19

[1]	(a) Kouznetsov, V. V.; Arenas, D. R. M.; Arvelo, F.; Forero, J. S. B.; Sojo, F.; Munoz, A. Lett. Drug Des. Discovery 2010, 7, 632. doi: 10.2174/157018010792929577
	(b) Rottmann, M.; McNamara, C.; Yeung, B. S. K.; Lee, M. C. S.; Zou, B.; Russell, B.; Seitz, P.; Plouffe, D. M.; Dharia, N. V.; Tan, J.; Cohen, S. B.; Spencer, K. R.; Gonzalez-Paez, G.; Lakshiminarayana, S. B.; Goh, A.; Suwanarusk, R.; Jegla, T.; Schmitt, E. K.; Beck, H.-P.; Brun, R.; Nosten, F.; Renia, L.; Dartois, V.; Keller, T. H.; Fidock, D. A.; Winzeler, E. A.; Diagana, T. T. Science 2010, 329, 1175. doi: 10.1126/science.1193225
	(c) Yeung, B. K. S.; Zou, B.; Rottmann, M.; Lakshminarayana, S. B.; Ang, S. H.; Leong, S. Y.; Tan, J.; Wong, J.; Keller-Maerki, S.; Fischli, C.; Goh, A.; Schmitt, E. K.; Krastel, P.; Francotte, E.; Kuhen, K.; Plouffe, D.; Henson, K.; Wagner, T.; Winzeler, E. A.; Petersen, F.; Brun, R.; Dartois, V.; Diagana, T. T.; Keller, T. H. J. Med. Chem. 2010, 53, 5155. doi: 10.1021/jm100410f
	(d) Lesma, G.; Landoni, N.; Sacchetti, A.; Silvani, A. Tetrahedron 2010, 66, 4474. doi: 10.1016/j.tet.2010.04.077
	(e) Ding, Q.; Liu, J.-J.; Zhang, Z. WO 2007104714, 2007.
[2]	(a) Kim, J.; Park, S. Y.; Jung, M.; Jang, W. C.; Ko, H. M. Tetrahedron Lett. 2022, 88, 153512. doi: 10.1016/j.tetlet.2021.153512
	(b) Jang, W. C.; Jung, M.; Ko, H. M. Org. Lett. 2021, 23, 1510. doi: 10.1021/acs.orglett.1c00292
	(c) Wang, C.-H.; Reilly, J.; Brand, N.; Schwartz, S.; Alluri, S.; Chan, T.-M.; Buevich, A. V.; Ganguly, A. K. Tetrahedron Lett. 2021, 51, 6213. doi: 10.1016/j.tetlet.2010.09.010
[3]	(a) Hajra, S.; Jana, B. Org. Lett. 2017, 19, 4778. doi: 10.1021/acs.orglett.7b02150
	(b) Yang, M.-C.; Peng, C.; Huang, H.; Yang, L.; He, X.-H.; Huang, W.; Cui, H.-L.; He, G.; Han, B. Org. Lett. 2017, 19, 6752. doi: 10.1021/acs.orglett.7b03516
	(c) Homquist, M.; Blay, G.; Muñoz, M. C.; Pedro, J. R. Adv. Synth. Catal. 2015, 357, 3857. doi: 10.1002/adsc.201500716
[4]	Nakamura, S.; Matsuzaka, K.; Hatanaka, T.; Funahashi, Y. Org. Lett. 2020, 22, 2868. doi: 10.1021/acs.orglett.0c00289 pmid: 32049543
[5]	Chang, Z.; Ye, C.; Fu, J.; Chigumbu, P.; Zeng, X.; Wang, Y.; Jiang, C.; Han, X. Adv. Synth. Catal. 2019, 361, 5516. doi: 10.1002/adsc.v361.24
[6]	(a) Wang, Y.-H.; Tian, J.-S.; Tan, P.-W.; Cao, Q.; Zhang, X.-X., Cao, Z.-Y.; Zhou, F.; Wang, X.; Zhou, J. Angew. Chem., Int. Ed. 2020, 59, 1634. doi: 10.1002/anie.v59.4
	(b) Wang, Y.; Ready, J. M. Org. Lett. 2012, 14, 2308. doi: 10.1021/ol300724c
[7]	(a) Bianchini, G.; Ribelles, P.; Becerra, D.; Ramosa, M. T.; Menéndez, J. C. Org. Chem. Front. 2016, 3, 412. doi: 10.1039/C6QO00037A
	(b) Gao, H.; Sun, J.; Yan, C.-G. Synthesis 2014, 46, 489. doi: 10.1055/s-00000084
	(c) Zhang, H.-H.; Sun, X.-X.; Liang, J.; Wang, Y.-M.; Zhao, C.-C.; Shi, F. Org. Biomol. Chem. 2014, 12, 9539. doi: 10.1039/C4OB01741B
	(d) Shi, F.; Xing, G.-J.; Zhu, R.-Y.; Tan, W.; Tu, S. Org. Lett. 2013, 15, 128. doi: 10.1021/ol303154k
	(e) Kouznetsov, V. V.; Forero, J. S. B.; Torres, D. F. A. Tetrahedron Lett. 2008, 49, 5855. doi: 10.1016/j.tetlet.2008.07.096
[8]	Wang, X.-W.; Huang, W.-J.; Wang, H.; Wu, B.; Zhou, Y.-G. Org. Lett. 2022, 24, 1727. doi: 10.1021/acs.orglett.2c00368
[9]	(a) Gao, Y.-T.; Jin, X.-Y.; Liu, Q.; Liu, A.-D.; Cheng, L.; Wang, D.; Liu, L. Molecules 2018, 23, 2265. doi: 10.3390/molecules23092265
	(b) Ohmatsu, K.; Ando, Y.; Nakashima, T.; Ooi, T. Chem 2016, 1, 802. doi: 10.1016/j.chempr.2016.10.012
	(c) Fuchs, J. R.; Funk, R. L. Org. Lett. 2005, 7, 677. doi: 10.1021/ol047532v
[10]	(a) Mu, B.-S.; Zhang, Z.-H.; Wu, W.-B.; Yu, J.-S.; Zhou, J. Acta Chim. Sinica 2021, 79, 685. (in Chinese) doi: 10.6023/A21040131
	(穆博帅, 张志豪, 武文彪, 余金生, 周剑, 化学学报, 2021, 79, 685.) doi: 10.6023/A21040131
	(b) Bertuzzi, G.; Bernardi, L.; Fochi, M. Catalysts 2018, 8, 632. doi: 10.3390/catal8120632
	(c) Ding, Q.; Zhou, X.; Fan, R. Org. Biomol. Chem. 2014, 12, 4807. doi: 10.1039/C4OB00371C
	(d) Ahamed, M.; Todd, M. H. Eur. J. Org. Chem. 2010, 5935.
[11]	(a) Pappoppula, M.; Cardoso, F. S. P.; Garrett, B. O.; Aponick, A. Angew. Chem., Int. Ed. 2015, 54, 15202. doi: 10.1002/anie.201507848 pmid: 26514098
	(b) Black, D. A.; Beveridge, R. E.; Arndtsen, B. A. J. Org. Chem. 2008, 73, 1906. doi: 10.1021/jo702293h pmid: 26514098
	(c) Sun, Z.; Yu, S.; Ding, Z.; Ma, D. J. Am. Chem. Soc. 2007, 129, 9300. doi: 10.1021/ja0734849 pmid: 26514098
	(d) Taylor, A. M.; Schreiber, S. L. Org. Lett. 2006, 8, 143. doi: 10.1021/ol0526165 pmid: 26514098
[12]	(a) Guo, Y.; Reis, M. C.; Kootstra, J.; Harutyunyan, S. R. ACS Catal. 2021, 11, 8476. doi: 10.1021/acscatal.1c01544
	(b) Fernandez-Ibanez, M. A.; Macia, B.; Pizzuti, M. G.; Minnaard, A. J.; Feringa, B. L. Angew. Chem., Int. Ed. 2009, 48, 9339. doi: 10.1002/anie.v48:49
[13]	(a) Lutz, J. P.; Chau, S. T.; Doyle, A. G. Chem. Sci. 2016, 7, 4105. doi: 10.1039/C6SC00702C
	(b) Chau, S. T.; Lutz, J. P.; Wu, K.; Doyle, A. G. Angew. Chem., Int. Ed. 2013, 52, 9153. doi: 10.1002/anie.201303994
[14]	(a) Robinson, D. J.; Spurlin, S. P.; Gorden, J. D.; Karimov, R. R. ACS Catal. 2020, 10, 51. doi: 10.1021/acscatal.9b03874 pmid: 26879692
	(b) Wang, Y.; Liu, Y.; Zhang, D.; Wei, H.; Shi, M.; Wang, F. Angew. Chem., Int. Ed. 2016, 55, 3776. doi: 10.1002/anie.201511663 pmid: 26879692
	(c) Nadeau, C.; Aly, S.; Belyk, K. J. Am. Chem. Soc. 2011, 133, 2878. doi: 10.1021/ja111540g pmid: 26879692
[15]	(a) Yang, P.; Wang, Q.; Cui, B.-H.; Zhang, X.-D.; Liu, H.; Zhang, Y.-Y.; Liu, J.-L.; Huang, W.-Y.; Liang, R.-X.; Jia, Y.-X. J. Am. Chem. Soc. 2022, 144, 1087. doi: 10.1021/jacs.1c11092
	(b) Lou, S.-J.; Luo, G.; Yamaguchi, S.; An, K.; Nishiura, M.; Hou, Z. J. Am. Chem. Soc. 2021, 143, 20462. doi: 10.1021/jacs.1c10743
[16]	Zhang, M.; Chen, B.; Ge, C.; Liu, R.; Gao, J.; Jia, Y. Chin. J. Org. Chem. 2016, 36, 1636. (in Chinese) doi: 10.6023/cjoc201602007
	(张鸣頔, 陈斌, 葛晨, 刘人荣, 高建荣, 贾义霞, 有机化学, 2016, 36, 1636.) doi: 10.6023/cjoc201602007
[17]	Zhang, M.; Liu, R.; Gao, J.; Jia, Y. Chin. J. Org. Chem. 2017, 37, 652. (in Chinese) doi: 10.6023/cjoc201610009
	(张鸣頔, 刘人荣, 高建荣, 贾义霞, 有机化学, 2017, 37, 652.) doi: 10.6023/cjoc201610009
[18]	(a) Zhu, Z.; Xiao, J.; Li, M.; Shi, Z. Angew. Chem., Int. Ed. 2022, 61, e2022013.
	(b) Jiang, X.; Jiang, H.; Yang, Q.; Cheng, Y.; Lu, L.-Q.; Tunge, J. A.; Xiao, W.-J. J. Am. Chem. Soc. 2022, 144, 8347. doi: 10.1021/jacs.2c02481
[19]	Heinz, C.; Lutz, J. P.; Simmons, E. M.; Miller, M. M.; Ewing, W. R.; Doyle, A. G. J. Am. Chem. Soc. 2018, 140, 2292. doi: 10.1021/jacs.7b12212

Entry	Solvent	Catalyst	Ligand	Yield^b/%
1	THF	Ni(PPh₃)₂Br₂	Bpy	55
2	DMF	Ni(PPh₃)₂Br₂	Bpy	0
3	MeOH	Ni(PPh₃)₂Br₂	Bpy	0
4	Dioxane	Ni(PPh₃)₂Br₂	Bpy	62
5	Dioxane	NiBr₂•DME	Bpy	<5
6	Dioxane	Ni(PCy₃)₂Cl₂	Bpy	46
7^c	Dioxane	Ni(PPh₃)₂Br₂	Bpy	52
8^d	Dioxane	Ni(PPh₃)₂Br₂	Bpy	48
9	Dioxane	Ni(PPh₃)₂Br₂	1,10-Phen	65
10	Dioxane	Ni(PPh₃)₂Br₂	L1	55
11	Dioxane	Ni(PPh₃)₂Br₂	L2	60
12	Dioxane	Ni(PPh₃)₂Br₂	L3	58
13^e	Dioxane	Ni(PPh₃)₂Br₂	DMAP	62
14^f	Dioxane	Ni(PPh₃)₂Br₂	DMAP	71
15^g	Dioxane	Ni(PPh₃)₂Br₂	DMAP	0
16^h	Dioxane	Ni(PPh₃)₂Br₂	DMAP	0
17	Dioxane		DMAP	0

Entry	Solvent	Catalyst	Ligand	Yield^b/%
1	THF	Ni(PPh₃)₂Br₂	Bpy	55
2	DMF	Ni(PPh₃)₂Br₂	Bpy	0
3	MeOH	Ni(PPh₃)₂Br₂	Bpy	0
4	Dioxane	Ni(PPh₃)₂Br₂	Bpy	62
5	Dioxane	NiBr₂•DME	Bpy	<5
6	Dioxane	Ni(PCy₃)₂Cl₂	Bpy	46
7^c	Dioxane	Ni(PPh₃)₂Br₂	Bpy	52
8^d	Dioxane	Ni(PPh₃)₂Br₂	Bpy	48
9	Dioxane	Ni(PPh₃)₂Br₂	1,10-Phen	65
10	Dioxane	Ni(PPh₃)₂Br₂	L1	55
11	Dioxane	Ni(PPh₃)₂Br₂	L2	60
12	Dioxane	Ni(PPh₃)₂Br₂	L3	58
13^e	Dioxane	Ni(PPh₃)₂Br₂	DMAP	62
14^f	Dioxane	Ni(PPh₃)₂Br₂	DMAP	71
15^g	Dioxane	Ni(PPh₃)₂Br₂	DMAP	0
16^h	Dioxane	Ni(PPh₃)₂Br₂	DMAP	0
17	Dioxane		DMAP	0

镍催化吡啶/喹啉鎓盐分子内去芳构化芳基加成反应