过渡金属催化联烯胺类化合物的碳氢化反应研究进展

doi:10.6023/cjoc202406007

摘要/Abstract

联烯胺作为一种富电子联烯类化合物, 由于其具有不同的反应位点和较高的反应活性, 近年来受到了广泛的关注。联烯胺的双重反应性允许对氮原子的C1-C3位点进行区域和立体选择性的官能团化。过渡金属催化联烯胺官能化以选择性地获得近端或远端加合物,在构建复杂的药物和天然产物骨架方面具有重要意义。本文综述了近年来在联烯胺化合物的碳氢化反应开发方面的进展。综述中的实例根据所使用的过渡金属类型进行分类,此外,本文还简要讨论了反应机理,对于碳氢化反应的选择性调控和开发新反应类型至关重要。

关键词: 联烯胺, 碳氢化, 官能团化, 区域选择性

As an electron-rich diene compound, N-allenamines have received wide spread attention in recent years due to its different reaction sites and high reactivity. The dual reactivity of N-allenamines enables functionalization at C1-C3 sites of the nitrogen atom, facilitating region- and stereoselective modifications. The transition metal-catalyzed functionalization of N-allenamines, which selectively yields either proximal or distal adducts, plays a crucial role in the synthesis of complex frameworks in drugs and natural products. The examples in the review are classified based on the type of transition metal used. In addition, this review briefly discusses the reaction mechanism, which is crucial for selective regulation of hydrocarbonnation reactions and the development of new reaction types.

Key words: N-allenamines, hydrocarbonnation, functionalization, regioselectivity

引用此文

王君伟, 薛皓, 曲英瑜, 姜若楠, 闫法超, 刘会. 过渡金属催化联烯胺类化合物的碳氢化反应研究进展[J]. 有机化学, doi: 10.6023/cjoc202406007.

Junwei Wang, Hao Xue, Yingyu Qu, Ruonan Jiang, Fachao Yan, Hui Liu. Research Progress on Transition Metal Catalyzed Hydrocarbonnation Reactions of N-allenamines[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202406007.

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参考文献

[1] Burton, B. S.; Pechman, H. V. Chem. Ber. 1887, 20, 145-149.
[2] Ma, S. Chem. Rev. 2005, 105, 2829-2872.
[3] Ma, S. Acc. Chem. Res. 2009, 42, 1679-1688.
[4] Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067-3126.
[5] Nájera, C.; Beletskaya, I. P.; Yus, M. Chem. Soc. Rev. 2019, 48, 4515-4618.
[6] Zhan, G.; Du, W.; Chen, Y.-C. Chem. Soc. Rev. 2017, 46, 1675-1692.
[7] Hubert, A.; Viehe, H. J. Chem. Soc. C 1968, 228-230.
[8] Wei, L-L.; Xiong, H.; Hsung, R. P. Acc. Chem. Res. 2003, 36, 773-782.
[9] Hourtoule, M.; Miesch, L. Org. Biomol. Chem. 2022, 20, 9069-9084.
[10] Zhang, J.; Liang, W.; Yang, Y.; Yan, F.; Liu, H. Chin. J. Org. Chem. 2024, 44, 335-348.
[11] Blieck, R.; Taillefer, M.; Monnier, F. Chem. Rev. 2020, 120, 13545-13598.
[12] De Renzi, A.; Panunzi, A.; Saporito, A.; Vitagli-ano, A. J. Chem. Soc., Perkin Trans. 2 1983, 993-996.
[13] Cui, J.; Meng, L.; Chi, X.; Liu, Q.; Zhao, P.; Zhang, D.; Chen, L.; Li, X.; Dong, Y.; Liu, H. Chem. Commun. 2019, 55, 4355-4358.
[14] (a) Dong, X.; Xu, L.-P.; Yang, Y.; Liu, Y.; Li, X.; Liu, Q.; Zheng, L.; Wang, F.; Liu, H. Org. Chem. Front. 2021, 8, 6009-6018.
(b) Sun, X.; Dong, X.; Liu, H.; Liu, Y. Adv. Synth. Catal. 2021, 363,1527-1558.
(c) Dong, X.; Hou, Y.; Meng, F.; Liu, H-B.; Liu, H. Chin. J. Org. Chem. 2017, 37, 1088-1098.
(d) Liu, Q.; Dong, X.; Li, J.; Xiao, J.; Dong, Y.; Liu, H. ACS Catal. 2015, 5, 6111-6137.
[15] Du, X.; Zhao, H.; Li, X.; Zhang, L.; Dong, Y.; Wang, P.; Zhang, D.; Liu, Q.; Liu, H. J. Org. Chem. 2021, 86, 13276-13288.
[16] Liang, H.; Yan, F.; Dong, X.; Liu, Q.; Wei, X.; Liu, S.; Dong, Y.; Liu, H. Chem. Commun. 2017, 53, 3138-3141.
[17] Yan, F.; Liang, H.; Song, J.; Cui, J.; Liu, Q.; Liu, S.; Wang, P.; Dong, Y.; Liu, H. Org. Lett. 2017, 19, 86-89.
[18] Yan, F.; Liang, H.; Ai, B.; Liang, W.; Jiao, L.; Yao, S.; Zhao, P.; Liu, Q.; Dong, Y.; Liu, H. Org. Biomol. Chem. 2019, 17, 2651-2656.
[19] Li, J.; Meng, L.; Du, X.; Liu, Q.; Xu, L.; Zhang, L.; Sun, F.; Li, X.; Zhang, D.; Xiao, X. Org. Chem. Front. 2020, 7, 3880-3886.
[20] Inamoto, K.; Yamamoto, A.; Ohsawa, K.; Hiroya, K.; Sakamoto, T. Chem. Pharm. Bull. 2005, 53, 1502-1507.
[21] Husinec, S.; Petkovic, M.; Savic, V.; Simic, M. Synthesis 2012, 44, 399-408.
[22] Blieck, R.; Taillefer, M.; Monnier, F. J. Org. Chem. 2019, 84, 11247-11252.
[23] Pradhan, T. R.; Lee, H. E.; Gonzalez-Montiel, G. A.; Cheong, P. H. Y.; Park, J. K. Chem. Eur. J. 2020, 26, 13826-13831.
[24] Liang, H.; Meng, L.; Chi, X.; Yao, S.; Chen, H.; Jiao, L.; Liu, Q.; Zhang, D.; Liu, H.; Dong, Y. Asian J. Org. Chem. 2018, 7, 1793-1796.
[25] Pradhan, T. R.; Kim, H. W.; Park, J. K. Angew. Chem. Int. Ed. 2018, 57, 9930-9935.
[26] Cao, C.; Yang, Y.; Li, X.; Liu, Y.; Liu, H.; Zhao, Z.; Chen, L. Eur. J. Org. Chem. 2021, 2021, 1538-1542.
[27] Chai, W.; Guo, B.; Zhang, Q.; Zi, W. Chem Catal. 2022, 2, 1428-1439.
[28] Jang, D.-J.; Lee, S.; Lee, J.; Moon, D.; Ho Rhee, Y. Angew. Chem. Int. Ed. 2021, 60, 22166-22171.
[29] Zhu, X.; Li, R.; Yao, H.; Lin, A. Org. Lett. 2021, 23, 4630-4634.
[30] Hé douin, J.; Schneider, C.; Gillaizeau, I.; Hoarau, C. Org. Lett. 2018, 20, 6027-6032.
[31] Wang, D.-C.; Yang, T.-T.; Qu, G.-R.; Guo, H.-M. J. Org. Chem. 2022, 87, 14284-14298.
[32] Wang, J.; Li, L.; Chai, M.; Ding, S.; Li, J.; Shang, Y.; Zhao, H.; Li, D.; Zhu, Q. ACS Catal. 2021, 11, 12367-12374.
[33] Wang, D.-C.; Cheng, P.-P.; Yang, T.-T.; Wu, P.-P.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2021, 23, 7865-7872.
[34] (a) Shen, Q.-W.; Wen, W.; Guo, Q.-X. Org. Lett. 2023, 25, 3163-3167.
(b) Guo, S.; Chen, J.; Yi, M.; Dong, L.; Lin, A.; Yao, H. Org. Chem. Front. 2021, 8, 1783-1788.
[35] Xue, Q.; Pu, Y.; Zhao, H.; Xie, X.; Zhang, H.; Wang, J.; Yan, L.; Shang, Y. Chem. Commun. 2024, 60, 3794-3797.
[36] Hajiloo Shayegan, M.; Li, Z.-Y.; Cui, X. Chem. Eur. J. 2022, 28, e202103402.
[37] Chen, C.; Tian, Z.; Liang, W.; Guo, J.; Xiao, P.; Wang, Z.; Zhang, L.; Liu, Q.; Liu, H. Asian J. Org. Chem. 2023, 12, e202300468.
[38] Skucas, E.; Zbieg, J. R.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 5054-5055.
[39] For ruthenium-catalyzed transfer hydrogenative coupling of alcohols to dienes, see: (a) Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6338-6339.
(b) Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14120-14122.
(c) Smejkal, T.; Han, H.; Breit, B.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 10366-10367.
[40] For ruthenium-catalyzed transfer hydrogenative coupling of alcohols to enynes, see: Patman, R. L.; Williams, V. M.; Bower, J. F.; Krische, M. J. Angew. Chem. Int. Ed. 2008, 47, 5220-5223.
[41] For ruthenium-catalyzed transfer hydrogenative coupling of alcohols to alkynes, see: (a) Patman, R. L.; Chaulagain, M. R.; Williams, V. M.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2066-2067.
(b) Williams, V. M.; Leung, J. C.; Patman, R. L.; Krische, M. J. Tetrahedron 2009, 65, 5024.
[42] For ruthenium-catalyzed transfer hydrogenative coupling of aldehydes to allenes, see: (a) Ngai, M.-Y.; Skucas, E.; Krische, M. J. Org. Lett. 2008, 10, 2705-2708.
(b) Skucas, E.; Zbieg, J. R.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 5054-5055.
(c) Grant, C. D.; Krische, M. J. Org. Lett. 2009, 11, 4485-4487.
[43] Zbieg, J. R.; McInturff, E. L.; Krische, M. J. Org. Lett. 2010, 12, 2514-2516.
[44] Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2007, 9, 4821.
[45] Kimber, M. C. Org. Lett. 2010, 12, 1128-1131.
[46] Fernández-Casado, J.; Nelson, R.; Mascareñas, J. L.; López, F. Chem. Commun. 2016, 52, 2909-2912.
[47] Singh, S.; Elsegood, M. R. J.; Kimber, M. C. Synlett. 2012, 2012, 565-568.
[48] An, J.; Lombardi, L.; Grilli, S.; Bandini, M. Org. Lett. 2018, 20, 7380-7383.
[49] Ocello, R.; De Nisi, A.; Jia, M.; Yang, Q.; Monari, M.; Giacinto, P.; Bottoni, A.; Miscione, G. P.; Bandini, M. Chem. Eur. J. 2015, 21, 18445-18453.
[50] (a) Yu, Y.; Zhang, Z.; Voituriez, A.; Rabasso, N.; Frison, G.; Marinetti, A.; Guinchard, X. Chem. Commun. 2021, 57, 10779-10782.
(b) Nicholls, L. D. M.; Wennemers, H. Chem. Eur. J. 2021, 27, 17559-17564.
[51] Jia, M.; Cera, G.; Perrotta, D.; Monari, M.; Bandini, M. Chem. Eur. J. 2014, 20, 9875-9878.
[52] Rocchigiani, L.; Jia, M.; Bandini, M.; Macchioni, A. ACS Catal. 2015, 5, 3911-3915.
[53] An, J.; Lombardi, L.; Grilli, S.; Bandini, M. Org. Lett. 2018, 20, 7380-7383.
[54] González-Gómez, Á.; Domínguez, G.; Pérez-Castells, J. Eur. J. Org. Chem. 2009, 2009, 5057-5062.
[55] Ma, Z.; He, S.; Song, W.; Hsung, R. P. Org. Lett. 2012, 14, 5736-5739.
[56] Liu, G.; Yu, S.; Hu, W.; Qiu, H. Chem. Commun. 2019, 55, 12675-12678.
[57] Banerjee, S.; Senthilkumar, B.; Patil, N. T. Org. Lett. 2019, 21, 180-184.
[58] Hill, A. W.; Elsegood, M. R. J.; Kimber, M. C. J. Org. Chem. 2010, 75, 5406-5409.
[59] Klake, R. K.; Gargaro, S. L.; Gentry, S. L.; Elele, S. O.; Sieber, J. D. Org. Lett. 2019, 21, 7992-7998.
[60] Ho, D.B.; Gargaro, S.; Klake, R. K.; Sieber, J. D. J. Org. Chem. 2022, 87, 2142-2153.
[61] Collinsa. S.; Sieber, J. D. Chem. Commun. 2023, 59, 10087-10100.
[62] Gargaro, S. L.; Klake, R. K.; Burns, K. L.; Elele, S. O.; Gentry, S. L.; Sieber, J. D. Org. Lett. 2019, 21, 9753-9758.
[63] Agrawal, T.; Martin, R. T.; Collins, S.; Wilhelm, Z.; Edwards, M. D.; Gutierrez, O.; Sieber, J. D. J. Org. Chem. 2021, 86, 5026-5046.
[64] Collins, S.; Sieber, J. D. Org. Lett. 2023, 25, 1425-1430.
[65] Klake, R. K.; Sieber, J. D. Org. Lett. 2023, 25, 4730-4734.
[66] Blieck, R.; Lemouzy, S.; van der Lee, A.; Taillefer, M.; Monnier, F. Org. Lett. 2021, 23, 9199-9203.
[67] Blieck, R.; Abed Ali Abdine, R.; Taillefer, M.; Monnier, F. Org. Lett. 2018, 20, 2232-2235.
[68] Abed Ali Abdine, R.; Pagès, L.; Taillefer, M.; Monnier, F. Eur. J. Org. Chem. 2020, 48, 7466-7469.
[69] Liu, Y.; De Nisi, A.; Cerveri, A.; Monari, M.; Bandini, M. Org. Lett. 2017, 19, 5034-5037.
[70] Liu, Y.; Cerveri, A.; De Nisi, A.; Monari, M.; Nieto Faza, O.; Lopez, C. S.; Bandini, M. Org. Chem. Front. 2018, 5, 3231-3239.
[71] Saito, N.; Sugimura, Y.; Sato, Y. Synlett 2014, 25, 736-740.
[72] Du, M.; Sun, Y.; Zhao, J.; Hu, H.; Sun, L.; Li, Y. Chin. Chem. Lett. 2023, 34, 108269.
[73] Gui, Y.-Y.; Chen, X.-W.; Mo, X.-Y.; Yue, J.-P.; Yuan, R.; Liu, Y.; Liao, L.-L.; Ye, J.-H.; Yu, D.-G. J. Am. Chem. Soc. 2024, 146, 2919-2927.
[74] 王野, 中国碳一分子催化转化领域的发展现状和未来挑战, 科学观察, 2023, DOI: 10.15978/j.cnki.1673-5668.202302001.
[75] Cui, J.; Song, J.; Liu, Q.; Liu, H.; Dong, Y. Chem. Asian J. 2018, 13, 482-495.
[76] Song, J.; Liu, Q.; Liu, H.; Jiang, X. Eur. J. Org. Chem. 2018, 6, 696-713.
[77] Shen, L.; Hsung, R. P. Org. Lett. 2005, 7, 775-778
[78] Mukherjee, R.; Basak, A. Synlett. 2012, 23, 877-880.
[79] Lu, N.; Zhang, Z.; Ma, N. Org. Lett. 2018, 20, 4318-4322.
[80] Yuan, X.; Tan, X.; Ding, N.; Liu, Y.; Li, X.; Zhao, Z. Org. Chem. Front. 2020, 7, 2725-2730.
[81] Koleoso, O. K.; Turner, M.; Plasser, F.; Kimber, M. C. Beilstein J. Org. Chem. 2020, 16, 1983.
[82] Koike, T.; Akita, M. Org. Chem. Front. 2016, 3, 1345-1349.
[83] Courant, T.; Masson, G. Chem. Eur. J. 2012, 18, 423-427.
[84] Quintavalla, A.; Veronesi, R.; Speziali, L.; Martinelli, A.; Zaccheroni, N.; Mummolo, L.; Lombardo, M. Adv. Synth. Catal. 2022, 364, 362-371.
[85] Wan, Y.; Zhang, J.; Chen, Y.; Kong, L.; Luo, F.; Zhu, G. Org. Biomol. Chem. 2017, 15, 7204-7211.
[86] Kondoh, A.; Ishikawa, S.; Aoki, T.; Terada, M. Chem. Commun. 2016, 52, 12513-12516.
[87] Zhang, J.; Wu, M.; Lu, W.; Wang, S.; Zhang, Y.; Cheng, C.; Zhu, G. J. Org. Chem. 2017, 82, 11134-11140.
[88] Brasholz, M.; Reissig, H.-U.; Zimmer, R. Acc. Chem. Res. 2009, 42, 45-56.
[89] Quintavalla, A.; Veronesi, R.; Speziali, L.; Martinelli, A.; Zaccheroni, N.; Mummolo, L.; Lombardo, M. Adv. Synth. Catal. 2022, 364, 362-371.