铱催化异羟肟酸衍生物参与的分子间N—N键偶联反应合成酰肼

doi:10.6023/cjoc202105044

摘要/Abstract

报道了一类铱催化下异羟肟酸衍生物作为酰基氮宾前体参与的分子间N—N偶联合成酰肼化合物的反应. 与之前报道的二噁唑酮参与的反应不同, 该类氮宾前体不仅可以合成N-酰基肼类化合物, 又可以用于N-氧酰基肼类化合物的合成. 计算化学研究说明分子内氢键辅助N—O键断裂脱酸形成金属酰基氮宾中间体可能是决速步, 随后芳胺在氢键辅助下亲核进攻金属酰基氮宾形成N—N键.

关键词: 铱催化, 氮宾, 氮氮偶联, 酰肼, N—H插入

An iridium-catalyzed intermolecular N—N coupling reaction using various N-benzoyloxyamides as acyl nitrene precursor for hydrazide synthesis has been developed. Unlike the carboxylic acid-derived dioxazolones used in previous report, this type of precursors allows the efficient synthesis of both acyl and oxycarbonyl substituted hydrazines from readily accessible precursors. Computational chemistry studies indicated that formation of the metal-acylnitrenoid intermediates via intramolecular hydrogen bond-assisted N—O cleavage may be the rate-determining step, and the subsequent nucleophilic attack of metal-acylnitrenoid by arylamines may be assisted by Cl…HN hydrogen bond to form the N—N bond.

Key words: iridium catalysis, nitrene, N—N coupling, hydrazide, N—H insertion

引用此文

宋方方, 朱士阳, 王浩, 陈弓. 铱催化异羟肟酸衍生物参与的分子间N—N键偶联反应合成酰肼[J]. 有机化学, 2021, 41(10): 4050-4058.

Fangfang Song, Shiyang Zhu, Hao Wang, Gong Chen. Iridium-Catalyzed Intermolecular N—N Coupling for Hydrazide Synthesis Using N-Benzoyloxycarbamates as Acyl Nitrene Precursor[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4050-4058.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 5

图式1. 金属酰基氮宾参与的N—N偶联反应

Scheme 1. Metal-acylnitrenoid-mediated N—N coupling reaction

Entry	Variation from the standard conditions	Yield^a/%
1	Standard condition	97 (94)^b
2	No [Cp*IrCl₂]₂	No reaction
3	Solvent free	92
4	[1]=0.1 mol/L	95
5	1.2 equiv. 2e was added	82
6	HFIP as solvent	No reaction
7	DCE as solvent	93
8	Ar atmosphere	92
9	FeCl₂•4H₂O (5 mol%) as catalyst	No reaction
10	T=60 ℃	77
11	AgSbF₆ (5 mol%)	15

表1. 反应条件优化

Table 1. Optimization of reaction conditions

表2. 酰基氮宾底物拓展

Table 2. Substrate scope of acylnitrenoid precursors

表3. N-烷基芳胺类底物拓展

Table 3. Substrate scope of N-alkyl arylamines

图1. N—N偶联反应势能图

Figure 1. Energy profiles of the N—N coupling reaction Calculations were performed at the M06-D3(0)/6-311+G**-SDD(Ir)- (SMD-CHCl3)//B3LYP-D3(BJ)/6-31G*-Lanl2dz(Ir) level of theory, kcal•mol–1.

参考文献 18

[1]	(a) Ke, S.; Sun, T.; Liang, Y.; Yang, Z. Chin. J. Org. Chem. 2010, 30, 1820. (in Chinese)
	(柯少勇, 孙婷婷, 梁英, 杨自文, 有机化学, 2010, 30, 1820.)
	(b) Blair, L. M.; Sperry, J. J. Nat. Prod. 2013, 76, 794. doi: 10.1021/np400124n
	(c) Chen, L.; Deng, Z.; Zhao, C. ACS Chem. Biol. 2021, 16, 559. doi: 10.1021/acschembio.1c00052
[2]	(a) Okuhara, M.; Kuroda, Y.; Goto, T.; Okamoto, M.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1980, 33, 13. pmid: 16441076
	(b) Ogita, T.; Gunji, S.; Fukazawa, Y.; Terahara, A.; Kinoshita, T.; Nagaki, H.; Beppu, T. Tetrahedron Lett. 1983, 24, 2283. doi: 10.1016/S0040-4039(00)81904-8 pmid: 16441076
	(c) Broberg, A.; Menkis, A.; Vasiliauskas, R. J. Nat. Prod. 2006, 69, 97. pmid: 16441076
	(d) Wang, K.-K. A.; Ng, T. L.; Wang, P.; Huang, Z.; Balskus, E. P.; van der Donk, W. A. Nat. Commun. 2018, 9, 3687. doi: 10.1038/s41467-018-06083-7 pmid: 16441076
[3]	Forquet, V.; Sabaté, C. M.; Jacob, G.; Guelou, Y.; Delalu, H.; Darwich, C. Chem.-Asian J. 2015, 10, 1668. doi: 10.1002/asia.v10.8
[4]	Diccianni, J. B.; Hu, C.; Diao, T. Angew. Chem.,Int. Ed. 2016, 55, 7534. doi: 10.1002/anie.v55.26
[5]	(a) Ragnarsson, U. Chem. Soc. Rev. 2001, 30, 205. doi: 10.1039/b010091a pmid: 11700143
	(b) Wolter, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803. pmid: 11700143
[6]	(a) Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595. pmid: 10823188
	(b) Feng, G.; Wang, X.; Jin, J. Eur. J. Org. Chem. 2019, 6728. pmid: 10823188
	(c) Chen, J.; Shen, X.; Lu, Z. J. Am. Chem. Soc. 2020, 142, 14455. doi: 10.1021/jacs.0c07258 pmid: 10823188
[7]	Guo, Q.; Lu, Z. Synthesis 2017, 49, 3835. doi: 10.1055/s-0036-1588512
[8]	(a) Rosen, B. R.; Werner, E. W.; O'Brien, A. G.; Baran, P. S. J. Am. Chem. Soc. 2014, 136, 5571. doi: 10.1021/ja5013323 pmid: 33974802
	(b) Pandit, P.; Yamamoto, K.; Nakamura, T.; Nishimura, K.; Kurashige, Y.; Yanai, T.; Nakamura, G.; Masaoka, S.; Furukawa, K.; Yakiyama, Y.; Kawano, M.; Higashibayashi, S. Chem. Sci. 2015, 6, 4160. doi: 10.1039/C5SC00946D pmid: 33974802
	(c) Ryan, M. C.; Martinelli, J. R.; Stahl, S. S. J. Am. Chem. Soc. 2018, 140, 9074. doi: 10.1021/jacs.8b05245 pmid: 33974802
	(d) Feng, N.; Hou, Z.; Xu, H. Chin. J. Org. Chem. 2019, 39, 1424. (in Chinese) doi: 10.6023/cjoc201812007 pmid: 33974802
	(冯恩祺, 侯中伟, 徐海超, 有机化学, 2019, 39, 1424.) doi: 10.6023/cjoc201812007 pmid: 33974802
	(e) Yin, D.; Jin, J. Eur. J. Org. Chem. 2019, 2019, 5646. doi: 10.1002/ejoc.201900763 pmid: 33974802
	(f) Ryan, M. C.; Kim, Y. J.; Gerken, J. B.; Wang, F.; Aristov, M. M.; Martinelli, J. R.; Stahl, S. S. Chem. Sci. 2020, 11, 1170. doi: 10.1039/C9SC04305E pmid: 33974802
	(g) Vemuri, P. Y.; Patureau, F. W. Org. Lett. 2021, 23, 3902. doi: 10.1021/acs.orglett.1c01034 pmid: 33974802
[9]	(a) Wallace, R. G. Aldrichim. Acta 1980, 13, 3.
	(b) Vidal, J.; Hannachi, J. C.; Hourdin, G.; Mulatier, J. C.; Collet, A. Tetrahedron Lett. 1998, 39, 8845. doi: 10.1016/S0040-4039(98)01983-2
	(c) Kang, C. W.; Sarnowski, M. P.; Elbatrawi, Y. M.; Del Valle, J. R. J. Org. Chem. 2017, 82, 1833. doi: 10.1021/acs.joc.6b02718
	(d) Lei, L.; Li, C.; Mo, D. Chin. J. Org. Chem. 2019, 39, 2989. (in Chinese) doi: 10.6023/cjoc201904037
	(雷禄, 李承璟, 莫冬亮, 有机化学, 2019, 39, 2989.) doi: 10.6023/cjoc201904037
	(e) Zhang, Y.; He, J.; Song, P.; Wang, Y.; Zhu, S. CCS Chem. 2020, 2, 2259.
[10]	(a) Li, J.; Cisar, J. S.; Zhou, C.-Y.; Vera, B.; Williams, H.; Rodríguez, A. D.; Cravatt, B. F.; Romo, D. Nat. Chem. 2013, 5, 510. doi: 10.1038/nchem.1653
	(b) Kono, M.; Harada, S.; Nemoto, T. Chem.-Eur. J. 2019, 25, 3119.
	(c) Maestre, L.; Dorel, R.; Pablo, O.; Escofet, I.; Sameera, W. M. C.; Alvarez, E.; Maseras, F.; Diaz-Requejo, M. M.; Echavarren, A. M.; Perez, P. J. J. Am. Chem. Soc. 2017, 139, 2216. doi: 10.1021/jacs.6b08219
	(d) Dehghany, M.; Eshon, J.; Roberts, J. M.; Schomaker, J. M. In Silver Catalysis in Organic Synthesis, Vol. 4, Eds.: Li, C.-J.; Bi, X., John Wiley & Sons, Weinheim, 2019, Chapter 8, pp. 439-532.
[11]	(a) Shimbayashi, T.; Sasakura, K.; Eguchi, A.; Okamoto, K.; Ohe, K. Chem.-Eur. J. 2019, 25, 3156. doi: 10.1002/chem.201803716 pmid: 30183111
	(b) van Vliet, K. M.; de Bruin, B. ACS Catal. 2020, 10, 4751. doi: 10.1021/acscatal.0c00961 pmid: 30183111
	(c) Wang, Y.-C.; Lai, X.-J.; Huang, K.; Yadav, S.; Qiu, G.; Zhang, L.; Zhou, H. Org. Chem. Front. 2021, 8, 1677. doi: 10.1039/D0QO01360A pmid: 30183111
	(d) Hong, S. Y.; Hwang, Y.; Lee, M.; Chang, S. Acc. Chem. Res. 2021, 54, 2683. doi: 10.1021/acs.accounts.1c00198 pmid: 30183111
	(e) Wu, L.-Y.; Zhong, D.; Liu, W.-B. Chin. J. Org. Chem. 2021, 41, 4083. (in Chinese) pmid: 30183111
	(邬林洋, 钟大猷, 刘文博, 有机化学, 2021, 41, 4083.) pmid: 30183111
[12]	(a) Ng, K.-H.; Chan, A. S. C.; Yu, W.-Y. J. Am. Chem. Soc. 2010, 132, 12862. doi: 10.1021/ja106364r pmid: 30978019
	(b) Grohmann, C.; Wang, H.; Glorius, F. Org. Lett. 2013, 15, 3014. doi: 10.1021/ol401209f pmid: 30978019
	(c) John, A.; Byun, J.; Nicholas, K. M. Chem. Commun. 2013, 49, 10965. doi: 10.1039/c3cc46412a pmid: 30978019
	(d) Zhou, B.; Du, J.; Yang, Y.; Feng, H.; Li, Y. Org. Lett. 2014, 16, 592. doi: 10.1021/ol403477w pmid: 30978019
	(e) Shi, J.; Zhao, G.; Wang, X.; Xu, H. E.; Yi, W. Org. Biomol. Chem. 2014, 12, 6831. doi: 10.1039/C4OB00637B pmid: 30978019
	(f) Huh, S.; Hong, S. Y.; Chang, S. Org. Lett. 2019, 21, 2808. doi: 10.1021/acs.orglett.9b00791 pmid: 30978019
	(g) Wang, H.; Park, Y.; Bai, Z. Q.; Chang, S.; He, G.; Chen, G. J. Am. Chem. Soc. 2019, 141, 7194. doi: 10.1021/jacs.9b02811 pmid: 30978019
	(h) Guo, Q.; Ren, X.; Lu, Z. Org. Lett. 2019, 21, 880. doi: 10.1021/acs.orglett.8b03299 pmid: 30978019
	(i) Jung, H.; Keum, H.; Kweon, J.; Chang, S. J. Am. Chem. Soc. 2020, 142, 5811. doi: 10.1021/jacs.0c00868 pmid: 30978019
[13]	(a) Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., nt. Ed. 2005, 44, 5188. pmid: 32357006
	(b) Clayden, J.; Donnard, M.; Lefranc, J.; Tetlow, D. J. Chem. Commun. 2011, 47, 4624. doi: 10.1039/c1cc00049g pmid: 32357006
	(c) Zhou, H.; Hong, J.; Huang, J.; Chen, Z. Asian J. Org. Chem. 2017, 6, 817. doi: 10.1002/ajoc.v6.7 pmid: 32357006
	(d) Li, W. H.; Dong, L. Adv. Synth. Catal. 2018, 360, 1104. doi: 10.1002/adsc.v360.6 pmid: 32357006
	(e) Bakhoda, A.; Jiang, Q.; Badiei, Y. M.; Bertke, J. A.; Cundari, T. R.; Warren, T. H. Angew. Chem., nt. Ed. 2019, 58, 3421. pmid: 32357006
	(f) Yoshitake, M.; Hayashi, H.; Uchida, T. Org. Lett. 2020, 22, 4021. doi: 10.1021/acs.orglett.0c01373 pmid: 32357006
[14]	Wang, H.; Jung, H.; Song, F.; Zhu, S.; Bai, Z.; Chen, D.; He, G.; Chang, S.; Chen, G. Nat. Chem. 2021, 13, 378. doi: 10.1038/s41557-021-00650-0
[15]	Ball, R. G.; Graham, W. A. G.; Heinekey, D. M.; Hoyano, J. K.; McMaster, A. D.; Mattson, B. M.; Michel, S. T. Inorg. Chem. 1990, 29, 2023. doi: 10.1021/ic00335a051
[16]	Le Grel, P.; Salaün, A.; Mocquet, C.; Le Grel, B.; Roisnel, T.; Potel, M. J. Org. Chem. 2011, 76, 8756. doi: 10.1021/jo201390b
[17]	Han, S.; Shin, Y.; Sharma, S.; Mishra, N. K.; Park, J.; Kim, M.; Kim, M.; Jang, J.; Kim, I. S. Org. Lett. 2014, 16, 2494. doi: 10.1021/ol500865j
[18]	Zhan, F.; Liang, G. Angew. Chem., nt. Ed. 2013, 52, 1266.