Palladium-Catalyzed Cyclization of 1,6-Enynes

doi:10.6023/cjoc202401032

Abstract

Functionalized carbo- and hetero-cyclic compounds are widely found in natural products and other bioactive molecules, which are also important scaffolds with significant synthetic value. The cyclization of 1,n-enynes is one of the most atom-economic and efficient approaches. In particular, the palladium-catalyzed cyclization of 1,6-enynes has been extensively studied and has achieved significant advancements. This review focuses on the cyclization of 1,6-enynes initiated by nucleopalladation of alkynes, including hydropalladation, carbopalladation, halopalladation and oxypalladation. It was classified by the nucleopalladation and the recent developments in palladium-catalyzed 1,6-enyne cyclization over the past two decades are systematically summarized. Special emphasis is placed on the asymmetric reactions, and reaction mechanisms, along with further prospects of this field.

Key words: palladium catalysis, 1,6-enynes, cyclization reaction, nucleopalladation, carbocyclic compounds, heterocyclic compounds

Cite this article

Wenjuan Liu, Pinhong Chen. Palladium-Catalyzed Cyclization of 1,6-Enynes[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2077-2091.

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Fig. & Tab. 38

Scheme 1. Pd-catalyzed cycloisomerization of 1,6-enynes

Scheme 2. Initial pathways of Pd-catalyzed cyclization of 1,n- enynes

Scheme 3. Pd-catalyzed cyclization of 1,6-enynes for the synthesis of 1,3-dienes

Scheme 4. Pd-catalyzed cyclization of 1,6-enynes for the synthesis of γ,δ-unsaturated carbonyl compounds

Scheme 5. Pd-catalyzed enantioselective cyclization of 1,6- enynes with chiral diphosphine ligands

Scheme 6. Pd-catalyzed enantioselective cyclization of 1,6- enynes with chiral N,P ligands

Scheme 7. Pd-catalyzed enantioselective hydroesterificative cyclization of 1,6-enynes

Scheme 8. Pd-catalyzed borylative cyclization of 1,6-enynes

Scheme 9. Pd-catalyzed halogenative cyclization of 1,6-enynes

Scheme 10. Cationic Pd-catalyzed reducitve cyclization of 1,6-enynes

Scheme 11. Pd-catalyzed endo-cyclization of 1,6-enynes

Scheme 12. Pd-catalyzed endo-cyclization of 1,6-enynes

Scheme 13. Pd-catalyzed arylcyclization of 1,6-enynes bearing allyl chloride

Scheme 14. Pd-catalyzed arylcyclization of 1,6-enynes for the synthesis of pyrroles

Scheme 15. Pd-catalyzed enantioselective arylcyclization of 1,6-enynes

Scheme 16. Pd-catalyzed arylcyclization of 1,6-enynes

Scheme 17. Pd-catalyzed diarylating carbocyclization of 1,6- enynes

Scheme 18. Halide effect in Pd-catalyzed halogenative cyclization of 1,6-enynes

Scheme 19. Pd-catalyzed halogenative cyclization of 1,6-enynes

Scheme 20. Pd-catalyzed halogenative cyclization of 1,6-enynes via cis-chloropalladation

Scheme 21. Pd-catalyzed chlorocyclization of 1,6-enynes with H2O2 as the oxidant

Scheme 22. Pd-catalyzed fluorocyclization of 1,6-enynes

Scheme 23. Pd-catalyzed enantioselective chlorocyclization of 1,6-enynes

Scheme 24. Pd-catalyzed enantioselective acetoxylcyclization of 1,6-enynes

Scheme 25. Ligand effect in Pd-catalyzed acetoxylcyclization of 1,6-enynes

Scheme 26. Pd-catalyzed enantioselective acetoxylcyclization of 1,6-enynes with chiral spiro bis(isoxazoline) (SPRIX) ligand

Scheme 27. Pd-catalyzed acetoxylcyclization of 1,6-enynes

Scheme 28. Pd-catalyzed enantioselective acetoxylcyclization of 1,6-enynes with cyclohexadienones

Scheme 29. Pd-catalyzed cascade cyclization of 1,6-enynes

Scheme 30. Mechanism of Pd-catalyzed cascade cyclization of 1,6-enynes

Scheme 31. Pd-catalyzed cascade cyclization of electron deficient 1,6-enynes

Scheme 32. Pd-catalyzed enantioselective cascade cyclization of 1,6-enynes

Scheme 33. Pd-catalyzed [3+2] cyclization of 1,6-enynes

Scheme 34. Mechanism of Pd-catalyzed [3+2] cyclization of 1,6-enynes

Scheme 35. Pd-catalyzed intramolecular cascade cyclization of 1,6-enynes

Scheme 36. Pd-catalyze Pd-catalyzed cascade cyclization of 1,6-enynes with H2O as the oxygen nucleophiles

Scheme 37. Pd-catalyzed cascade cyclization of 1,6-enynes with amides as nucleophiles

Scheme 38. Pd-catalyzed cascade cyclization of 1,6-enynes with thiocyanide as nucleophiles

References 55

[1]	(a) Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. J. Med. Chem. 2014, 57, 5845.
	(b) Hammder, N.; Leth, L. A.; Stiller, J.; Jensen, M. E.; Jørgensen, K. A. Chem. Sci. 2016, 7, 3649.
[2]	For selected reviews, see: (a) Xu, C.-H.; Li, Y.; Li, J.-H.; Xiang, J.-N.; Deng, W. Sci. China Chem. 2019, 62, 1463.
	(b) Chen, M.; Went, Y.; Lei, A. Prog. Chem. 2010, 22, 1341. (in Chinese)
	(陈茂, 翁玥, 雷爱文, 化学进展, 2010, 22, 1341.)
	(c) Michelet, V.; Toullec, P. Y.; Genêt, J.-P. Angew. Chem., Int. Ed. 2008, 47, 4268.
	(d) Tong, X.; Zhang, Z. Chin. J. Org. Chem. 2004, 24, 591. (in Chinese)
	(童晓峰, 张兆国, 有机化学, 2004, 24, 591.)
	(e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
	(f) Trost, B. M. Acc. Chem. Res. 1990, 23, 34.
	(g) Hu, L.-P.; Zhang, D.-R. Huang, X.-H.; Liu, F.-L; Li, X.; Teng, M.-Y.; Huang, G.-L. Chin. J. Chem. 2022, 40, 2756.
	(h) Liu, J.-X.; Xu, S.-Q.; Han, Y.-P.; Liang, Y.-M. Adv. Synth. Catal. 2024, 366, 1220.
[3]	Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1985, 107, 1781.
[4]	Takacs, J. M.; Zhu, J.; Chandramouli, S. V. J. Am. Chem. Soc. 1992, 124, 773.
[5]	Fairlamb, I. J. S. Angew. Chem., Int. Ed. 2004, 43, 1048.
[6]	Lu, X.; Zhu, G.; Wang. Z. Synlett 1998, 115.
[7]	(a) Huang, X.; Nguyen, M. H.; Pu, L.; Zhang, L.; Chi, Y. R.; Wu, Y.-D.; Zhou, J. S. Angew. Chem., Int. Ed. 2020, 59, 10814.
	(b) Li, Q.; Zhang, Y.; Liu, P.; Zhong, J.; Gong, B.; Yao, H.; Lin, A. Angew. Chem., Int. Ed. 2023, 62, e202211988.
[8]	Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268.
[9]	Trost, B. M.; Pedregal, C. J. Am. Chem. Soc. 1992, 114, 7292.
[10]	Oh, C. H.; Jung, H. H.; Kim, J. S.; Cho, S. W. Angew. Chem., Int. Ed. 2000, 39, 752. pmid: 10760858
[11]	Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249.
[12]	Hatano, M.; Mikami, K. J. Am. Chem. Soc. 2003, 125, 4704.
[13]	(a) Hatano, M.; Yamanaka, M.; Mikami, K. Eur. J. Org. Chem. 2003, 2552.
	(b) Hatano, M.; Mikami, K. Org. Biomol. Chem. 2003, 1, 3871.
[14]	Quan, X.; Liu, J.; Rabten, W.; Diomedi, S.; Singh, T.; Andersson, P. G. Eur. J. Org. Chem. 2016, 3427.
[15]	Ren, X.; Tang, L.; Shen, C.; Li, H.; Wang, P.; Dong, K. Org. Lett. 2021, 23, 3561.
[16]	Marco-Martínez, J.; López-Carrillo, V.; Buñuel, E.; Simancas, R.; Cárdenas, D. J. J. Am. Chem. Soc. 2007, 129, 1874. pmid: 17260998
[17]	Sun, D.; Zhou, B.; Liu, L.; Chen, X.; Hou, H.; Han, Y.; Yan, C.; Shi, Y.; Zhu, S. Org. Lett. 2023, 25, 4677.
[18]	Jia, X.; Petrone, D. A.; Lautens, M. Angew. Chem., Int. Ed. 2012, 51, 9870.
[19]	Petrone, D. A.; Franzoni, I.; Ye, J.; Rodríguez, J. F.; Poblador- Bahamonde, A. I.; Lautens, M. J. Am. Chem. Soc. 2017, 139, 3546. doi: 10.1021/jacs.7b00482 pmid: 28195710
[20]	Wu, W.; Chen, T.; Chen, J.; Han, X. J. Org. Chem. 2017, 83, 1033.
[21]	Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. 2004, 101, 5767.
[22]	Dong, M.; Qi, L.; Qian, J.; Yu, S.; Tong, X. J. Am. Chem. Soc. 2023, 145, 1973.
[23]	(a) Kawasaki, S.; Satoh, T.; Miura, M.; Nomura, M. J. Org. Chem. 2003, 68, 6836. pmid: 12919062
	(b) Satoh, T.; Ogino, S.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 2004, 43, 5063. pmid: 12919062
	(c) Oh, C. H.; Jung, H. H.; Kim, K. S.; Kim, N. Angew. Chem., Int. Ed. 2003, 42, 805. pmid: 12919062
	(d) For a review, see: Rajesh, M.; Kumar, G. R. Asian J. Org. Chem. 2023, 12, e202300106. pmid: 12919062
[24]	Zhu, G.; Zhang, Z. Org. Lett. 2003, 5, 3645.
[25]	Meng, T. J.; Hu, Y.; Wang, S. J. Org. Chem. 2010, 75, 582.
[26]	Meng, T.; Hu, Y.; Sun, Y.; Zhu, T.; Wang, S. Tetrahedron 2010, 66, 8648.
[27]	Shen, K.; Han, X.; Lu, X. Org. Lett. 2012, 14, 1756. doi: 10.1021/ol3003546 pmid: 22449236
[28]	Murthy, A. S.; Donikela, S.; Reddy, C. S.; Chegondi, R. J. Org. Chem. 2015, 80, 5566.
[29]	Shen, K.; Han, X.; Lu, X.; Hu, Z. Tetrahedron Lett. 2017, 58, 3768.
[30]	Jiang, M.; Jiang, T.; Bäckvall, J. E. Org. Lett. 2012, 14, 3538. doi: 10.1021/ol301551x pmid: 22716930
[31]	Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Imanaka, T.; Teranish, S. J. Org. Chem. 1979, 44, 55.
[32]	(a) Ma, S.; Lu, X. J. Chem. Soc., Chem. Commun. 1990, 733.
	(b) Ma, S.; Lu, X. J. Org. Chem. 1991, 56, 5120.
	(c) Ma, S.; Zhu, G.; Lu, X. J. Org. Chem. 1993, 58, 3692.
	(d) Ma, S.; Lu, X. J. Org. Chem. 1993, 58, 1245.
	(e) Ji, J.; Lu, X. Tetrahedron 1994, 50, 9067.
	(f) Ji, J. Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 1160.
	(g) Wang, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 5213.
[33]	Xie, X.; Lu, X.; Liu, Y.; Xu, W. J. Org. Chem. 2001, 66, 6545. pmid: 11578203
[34]	Zhu, G.; Zhang, Z. J. Org. Chem. 2005, 70, 3339.
[35]	Yin, G.; Liu, G. Angew. Chem., Int. Ed. 2008, 47, 5442.
[36]	Takenaka, K.; Hashimoto, S.; Takizawa, S.; Sasai, H. Adv. Synth. Catal. 2011, 353, 1067.
[37]	Peng, H.; Liu, G. Org. Lett. 2011, 13, 772.
[38]	Tang, J.; Zhang, L.; Wu, W.; Yang, S.; Jiang, H. Chem.-Eur. J. 2022, 28, e202202528.
[39]	(a) Lu, X.; Zhu, G.; Ma, S. Tetrahedron Lett. 1992, 33, 7205.
	(b) Wakabayashi, T.; Ishii, Y.; Murata, T.; Mizobe, Y.; Hidai, M. Tetrahedron Lett. 1995, 36, 5585.
[40]	Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604.
[41]	Zhang, Q.; Lu, X.; Han, X. J. Org. Chem. 2001, 66, 7676. pmid: 11701020
[42]	Song, J.; Shen, Q.; Xu, F.; Lu, X. Tetrahedron 2007, 63, 5148.
[43]	Xu, W.; Kong, A.; Lu, X. J. Org. Chem. 2006, 71, 3854.
[44]	Muthiah, C.; Arai, M. A.; Shinohara, T.; Arai, T.; Takizawa, S.; Sasai, H. Tetrahedron Lett. 2003, 44, 5201.
[45]	Zhao, L.; Lu, X.; Xu, W. J. Org. Chem. 2005, 70, 4059.
[46]	Bai, Y.-Q.; Wang, X.-W.; Wu, B.; Wang, X.-Q.; Liao, R.-Z.; Li, M.; Zhou, Y.-G. ACS Catal. 2023, 13, 9829.
[47]	Welbes, L. L.; Lyons, T. W.; Cychosz, K. A.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 5836.
[48]	Tong, X.; Beller, M.; Tse, M. K. J. Am. Chem. Soc. 2007, 129, 4906.
[49]	Liu, H.; Yu, J.; Wang, L.; Tong, X. Tetrahedron Lett. 2008, 49, 6924.
[50]	Tsujihara, T.; Takenaka, K.; Onitsuka, K.; Hatanaka, M.; Sasai, H. J. Am. Chem. Soc. 2009, 131, 3452. doi: 10.1021/ja809965e pmid: 19275254
[51]	Xu, T.; Wang, D.; Tong, X. Org. Lett. 2019, 21, 5368. doi: 10.1021/acs.orglett.9b02096 pmid: 31247755
[52]	Vinoth, P.; Vivekanand, T.; Suryavanshi, P. A.; Menéndez, J. C.; Sasai, H.; Sridharan, V. Org. Biomol. Chem. 2015, 13, 5175.
[53]	Liu, B.; Song, R.-J.; Ouyang, X.-H.; Li, Y.; Hu, M.; Li, J.-H. Chem. Commun. 2015, 51, 12819.
[54]	Chen, J.; Han, X.; Lu, X. Angew. Chem., Int. Ed. 2017, 56, 14698.
[55]	Malik, G.; Swyka, R. A.; Tiwari, V. K.; Fei, X.; Applegate, G. A.; Berkowitz, D. B. Chem. Sci. 2017, 8, 8050. doi: 10.1039/c7sc04083k pmid: 29568453

钯催化1,6-烯炔的环化反应研究