锆氢催化的酰胺硼氢化合成胺类化合物研究: 机理、使用范围和应用

doi:10.1016/S1872-2067(21)63853-6

催化学报 ›› 2021, Vol. 42 ›› Issue (11): 2059-2067.DOI: 10.1016/S1872-2067(21)63853-6

锆氢催化的酰胺硼氢化合成胺类化合物研究: 机理、使用范围和应用

韩波^a^,^c, 张炯^a, 焦海军^b^,^#(), 吴立朋^a^,^*()

^a中国科学院兰州化学物理研究所, 兰州化物所苏州研究院, 羰基合成与选择氧化国家重点实验室, 甘肃兰州730000, 中国
^b莱布尼茨催化研究所, 罗斯托克18059, 德国
^c中国科学院大学, 北京100049, 中国

收稿日期:2021-04-27 修回日期:2021-04-27 接受日期:2021-05-31 出版日期:2021-11-18 发布日期:2021-06-08
通讯作者: 焦海军,吴立朋
基金资助:
国家自然科学基金(91845108);国家自然科学基金(21901247);国家自然科学基金(21902167);江苏省自然科学基金(BK20180246)

Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application

Bo Han^a^,^c, Jiong Zhang^a, Haijun Jiao^b^,^#(), Lipeng Wu^a^,^*()

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, Gansu, China
^bLeibniz-Institut für Katalyse e. V. Albert-Einstein-Straße 29a, 18059 Rostock, Germany
^cUniversity of Chinese Academy of Sciences, Beijing 100049, China

Received:2021-04-27 Revised:2021-04-27 Accepted:2021-05-31 Online:2021-11-18 Published:2021-06-08
Contact: Haijun Jiao,Lipeng Wu
About author:^#E-mail: haijun.jiao@catalysis.de
^*Tel/Fax: +86-512-81880906; E-mail: lipengwu@licp.cas.cn;
Supported by:
National Natural Science Foundation of China(91845108);National Natural Science Foundation of China(21901247);National Natural Science Foundation of China(21902167);Natural Science Foundation of Jiangsu Province(BK20180246);“Innovation & Entrepreneurship Talents Plan" of Jiangsu Province

摘要/Abstract

摘要：

发展温和条件下胺类化合物的高效合成方法是催化与合成领域长期研究的课题. 其中, 酰胺还原因其原料来源广、易于合成而广受关注. 酰胺还原到胺需要选择性断裂C=O键, 因此该反应具有很大的挑战性. 传统酰胺还原方法需要使用当量的强还原试剂, 如四氢铝锂、硼氢化钠等, 且官能团兼容性较差. 使用氢气还原原子经济性最高, 也最有吸引力; 然而, 目前已报道的体系大都在高温(> 120^oC)或高压(>40 bar H2)的条件下进行. 虽然催化硼氢化可以在温和的条件下将羰基化合物还原, 但由于酰胺化合物惰性比较高, 其选择性的催化硼氢化研究则相对较少, 而且在温和条件下对三级、二级、一级酰胺都适用的例子依然非常有限.
本文采用前过渡金属锆氢催化剂实现了室温条件下酰胺选择性硼氢化制备胺类化合物, 并进行了详细的机理研究. 原位红外监测到反应过程中酰胺和硼烷逐渐减少, 目标产物逐渐增多; 但并未给出其他反应中间体的信息. 核磁研究以及对照实验结果表明, 反应中有苯甲醛的生成, 可能是反应中间体. 因此推测, 该催化体系经历了锆氢介导的酰胺C-N键断裂、重组、C-O键断裂这一特殊的酰胺键活化转化过程. DFT计算也证实了上述反应历程的可行性. 除一些常见官能团外, 本方法对羧酸酯、氰基、硝基、烯烃和炔烃这些可能被硼氢化的官能团同样具有兼容性. 而且本文体系对一些生物、药物分子衍生酰胺的硼氢化也可以顺利进行. 可见, 本文发展了一种温和条件下使用廉价催化剂和原料选择性合成胺类化合物的方法.

关键词: 锆, 酰胺, 硼氢化, 胺, 催化

Abstract:

Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C-O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C-N bond cleavage-reformation process, followed by C-O bond cleavage.

Key words: Zirconium, Amide, Hydroboration, Amine, Catalysis

韩波, 张炯, 焦海军, 吴立朋. 锆氢催化的酰胺硼氢化合成胺类化合物研究: 机理、使用范围和应用[J]. 催化学报, 2021, 42(11): 2059-2067.

Bo Han, Jiong Zhang, Haijun Jiao, Lipeng Wu. Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application[J]. Chinese Journal of Catalysis, 2021, 42(11): 2059-2067.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(21)63853-6

https://www.cjcatal.com/CN/Y2021/V42/I11/2059

图/表 7

Scheme 1. Catalytic deoxygenative amide reduction and carbonyl hydroboration: (a) catalytic deoxygenative amide reduction using sensitive and hazardous metal hydrides or H2 under harsh reaction conditions; (b) catalytic hydroboration of carbonyls without C-O bond cleavage; (c) catalytic deoxygenative hydroboration of amides and the present methodology, featuring mild reaction conditions, a broad substrate scope, and detailed mechanistic understanding.

Table 1 Zirconium-catalyzed amide hydroboration: optimization of reaction conditions.

Entry	Catalyst	Catalyst amount (mol%)	Solvent	2a Yield * (%)
1	Cp₂ZrCl₂	5	THF	trace
2	Cp₂ZrHCl	5	THF	60
3	Cp₂ZrH₂	5	THF	70
4	Cp₂ZrH₂	10	THF	95
5	Cp₂ZrH₂	5	DCM	68
6	Cp₂ZrH₂	5	Et₂O	67
7	Cp₂ZrH₂	5	Toluene	38
8	Cp₂ZrH₂	5	CH₃CN	7
9	Cp₂ZrH₂	5	1,4-Dioxane	trace
10	Cp₂ZrH₂	5	neat	85

Fig. 1. (a) Operando IR spectra of the standard catalytic reaction process. 1H NMR spectra of reactions using (b) 0.16 mmol of 1a, 0.2 mmol Cp2ZrH2 in 2 mL chloroform-d for 1 h; (c) 0.2 mmol of 1a, 0.01 mmol Cp2ZrH2 in 2 mL chloroform-d for 1 h; (d) 0.2 mmol of 1a, 0.01 mmol Cp2ZrH2, 0.6 mmol HBpin in 2 mL chloroform-d for 1 h, followed by the addition of 0.2 mmol 4-phenylbenzaldehyde to the reaction solution; (e) 0.2 mmol of 1a, 0.01 mmol Cp2ZrH2, 0.6 mmol HBpin in 2 mL chloroform-d for 1 h, followed by the addition of 0.2 mmol HNEt2 to the reaction solution.

Fig. 2. M06L computed Gibbs free energy profiles (ΔG, kcal/mol) for the parent reaction between 1a and HBpin catalyzed by Cp2ZrH2.

Fig. 3. Proposed reaction mechanism of Cp2ZrH2-catalyzed hydroboration of amides.

Scheme 2. Reaction conditions: 0.2 mmol amide, HBpin (0.6 mmol, 3 equiv.), Cp2ZrH2 (5 mol%) in a reaction tube, stirred for 12-24 h at room temperature; isolated yields after treatment of the reaction mixture with 1 N HCl in ether are given. a Reaction was performed with additional 0.5 mL THF; b 60 °C for 48 h; c rt for 36 h, NMR yield; d 100 °C for 36 h, NMR yield.

Scheme 3. Reaction conditions: 0.2 mmol amide, HBpin (3 equiv. per amide bond), Cp2ZrH2 (5 mol%) in a reaction tube and stirred for 16 h at room temperature; isolated yields after treatment of the reaction mixture with 1 N HCl in ether. aReaction was performed at 60 °C; bisolated yields of amines.

参考文献

[1]	S. A. Lawrence, Amines: synthesis, properties, and application. Cambridge University Press, New York, 2004.
[2]	S. H. Cho, J. Y. Kim, S. Y. Lee, S. Chang, Angew. Chem. Int. Ed., 2009, 48, 9127-9130.
[3]	S. N. Mlynarski, A. S. Karns, J. P. Morken, J. Am. Chem. Soc., 2012, 134, 16449-16451.
[4]	E. Valeur, M. Bradley, Chem. Soc. Rev., 2009, 38, 606-631.
[5]	V. R. Pattabiraman, J. W. Bode, Nature, 2011, 480, 471-479.
[6]	A. Ojeda-Porras, D. Gamba-Sánchez, J. Org. Chem., 2016, 81, 11548-11555.
[7]	R. M. de Figueiredo, J.-S. Suppo, J.-M Campagne, Chem. Rev., 2016, 116, 12029-12122.
[8]	D. Kaiser, A. Bauer, M. Lemmerer, N. Maulide, Chem. Soc. Rev., 2018, 47, 7899-7925.
[9]	G. Li, C.-L. Ji, X. Hong, M. Szostak, J. Am. Chem. Soc., 2019, 141, 11161-11172.
[10]	E. Massolo, M. Pirola, M. Benaglia, Eur. J. Org. Chem., 2020, 2020, 4641-4651.
[11]	L. Yang, L. Shi, C. Xia, F. Li, Chin. J. Catal., 2020, 41, 1152-1160.
[12]	X. Dai, B. Wang, A. Wang, F. Shi, Chin. J. Catal., 2019, 40, 1141-1146.
[13]	N. End, L. Macko, M. Zehnder, A. Pfaltz, Chem. Eur. J., 1998, 4, 818-824.
[14]	D. A. Evans, G. Borg, K. A. Scheidt, Angew. Chem. Int. Ed., 2002, 41, 3188-3191.
[15]	J. Pritchard, G. A. Filonenko, R. van Putten, E. J. M. Hensen, E. A. Pidko, Chem. Soc. Rev., 2015, 44, 3808-3833.
[16]	A. Volkov, F. Tinnis, T. Slagbrand, P. Trillo, H. Adolfsson, Chem. Soc. Rev., 2016, 45, 6685-6697.
[17]	H. C. Brown, P. Heim, J. Am. Chem. Soc., 1964, 86, 3566-3567.
[18]	M. L. Di Gioia, E. L. Belsito, A. Leggio, V. Leotta, E. Romio, C. Siciliano, A. Liguori, Tetrahedron Lett., 2015, 56, 2062-2066.
[19]	A. Chardon, E. Morisset, J. Rouden, J. Blanchet, Synthesis, 2018, 50, 984-997.
[20]	E. Balaraman, B. Gnanaprakasam, L. J. W. Shimon, D. Milstein, J. Am. Chem. Soc., 2010, 132, 16756-16758.
[21]	J. Coetzee, D. L. Dodds, J. Klankermayer, S. Brosinski, W. Leitner, A. M. Z. Slawin, D. J. Cole-Hamilton, Chem. Eur. J., 2013, 19, 11039-11050.
[22]	A. M. Smith, R. Whyman, Chem. Rev., 2014, 114, 5477-5510.
[23]	J. M. John, R. Loorthuraja, E. Antoniuk, S. H. Bergens, Catal. Sci. Technol., 2015, 5, 1181-1186.
[24]	M.-L. Yuan, J.-H Xie, S.-F Zhu, Q.-L Zhou, ACS Catal., 2016, 6, 3665-3669.
[25]	J. R. Cabrero-Antonino, R. Adam, V. Papa, M. Beller, Nat. Commun., 2020, 11, 3893.
[26]	M. J. Sgro, D. W. Stephan, Angew. Chem. Int. Ed., 2012, 51, 11343-11345.
[27]	T. J. Hadlington, M. Hermann, G. Frenking, C. Jones, J. Am. Chem. Soc., 2014, 136, 3028-3031.
[28]	D. Mukherjee, A. Ellern, A. D. Sadow, Chem. Sci., 2014, 5, 959-964.
[29]	C. C. Chong, R. Kinjo, ACS Catal., 2015, 5, 3238-3259.
[30]	N. Eedugurala, Z. Wang, U. Chaudhary, N. Nelson, K. Kandel, T. Kobayashi, I. I. Slowing, M. Pruski, A. D. Sadow, ACS Catal., 2015, 5, 7399-7414.
[31]	D. Mukherjee, H. Osseili, T. P. Spaniol, J. Okuda, J. Am. Chem. Soc., 2016, 138, 10790-10793.
[32]	G. Zhang, H. Zeng, J. Wu, Z. Yin, S. Zheng, J. C. Fettinger, Angew. Chem. Int. Ed., 2016, 55, 14369-14372.
[33]	S. R. Tamang, M. Findlater, J. Org. Chem., 2017, 82, 12857-12862.
[34]	V. L. Weidner, C. J. Barger, M. Delferro, T. L. Lohr, T. J. Marks, ACS Catal., 2017, 7, 1244-1247.
[35]	C. Erken, A. Kaithal, S. Sen, T. Weyhermüller, M. Hölscher, C. Werlé, W. Leitner, Nat. Commun., 2018, 9, 4521.
[36]	S. R. Tamang, M. Findlater, Dalton Trans., 2018, 47, 8199-8203.
[37]	V. Vasilenko, C. K. Blasius, L. H. Gade, J. Am. Chem. Soc., 2018, 140, 9244-9254.
[38]	C. J. Barger, A. Motta, V. L. Weidner, T. L. Lohr, T. J. Marks, ACS Catal., 2019, 9, 9015-9024.
[39]	Y. Lebedev, I. Polishchuk, B. Maity, M. Dinis Veloso Guerreiro, L. Cavallo, M. Rueping, J. Am. Chem. Soc., 2019, 141, 19415-19423.
[40]	B.-X. Leong, J. Lee, Y. Li, M.-C Yang, C.-K Siu, M.-D Su, C.-W So, J. Am. Chem. Soc., 2019, 141, 17629-17636.
[41]	L. Zhao, C. Hu, X. Cong, G. Deng, L. L. Liu, M. Luo, X. Zeng, J. Am. Chem. Soc., 2021, 143, 1618-1629.
[42]	N. L. Lampland, M. Hovey, D. Mukherjee, A. D. Sadow, ACS Catal., 2015, 5, 4219-4226.
[43]	S. Das, H. Karmakar, J. Bhattacharjee, T. K. Panda, Dalton Trans., 2019, 48, 11978-11984.
[44]	G. Zhang, J. Wu, S. Zheng, M. C. Neary, J. Mao, M. Flores, R. J. Trovitch, P. A. Dub, J. Am. Chem. Soc., 2019, 141, 15230-15239.
[45]	C. J. Barger, R. D. Dicken, V. L. Weidner, A. Motta, T. L. Lohr, T. J. Marks, J. Am. Chem. Soc., 2020, 142, 8019-8028.
[46]	P. Ye, Y. Shao, X. Ye, F. Zhang, R. Li, J. Sun, B. Xu, J. Chen, Org. Lett., 2020, 22, 1306-1310.
[47]	W. B. Yao, J. L. Wang, A. G. Zhong, S. L. Wang, Y. L. Shao, Org. Chem. Front., 2020, 7, 3515-3520.
[48]	S. R. Tamang, A. Singh, D. Bedi, A. R. Bazkiaei, A. A. Warner, K. Glogau, C. McDonald, D. K. Unruh, M. Findlater, Nat. Catal., 2020, 3, 154-162.
[49]	G. A. Olah, M. Arvanaghi, Angew. Chem. Int. Ed., 1981, 20, 878-879.
[50]	S. Nahm, S. M. Weinreb, Tetrahedron Lett., 1981, 22, 3815-3818.
[51]	J. T. Spletstoser, J. M. White, A. R. Tunoori, G. I. Georg, J. Am. Chem. Soc., 2007, 129, 3408-3419.
[52]	G. Pelletier, W. S. Bechara, A. B. Charette, J. Am. Chem. Soc., 2010, 132, 12817-12819.
[53]	W. S. Bechara, G. Pelletier, A. B. Charette, Nat. Chem., 2012, 4, 228-234.
[54]	V. Pace, W. Holzer, B. Olofsson, Adv. Synth. Catal., 2014, 356, 3697-3736.
[55]	L. Hie, N. F. Fine Nathel, T. K. Shah, E. L. Baker, X. Hong, Y.-F. Yang, P. Liu, K. N. Houk, N. K. Garg, Nature, 2015, 524, 79-83.
[56]	G. Meng, R. Szostak, M. Szostak, Org. Lett., 2017, 19, 3596-3599.
[57]	P. Lei, G. Meng, S. Shi, Y. Ling, J. An, R. Szostak, M. Szostak, Chem. Sci., 2017, 8, 6525-6530.
[58]	P. Gao, M. Szostak, Org. Lett., 2020, 22, 6010-6015.
[59]	G. Li, S. Ma, M. Szostak, Trends Chem., 2020, 2, 914-928.
[60]	T. B. Boit, M. M. Mehta, J. Kim, E. L. Baker, N. K. Garg, Angew. Chem. Int. Ed., 2021, 60, 2472-2477.
[61]	S. Yow, S. J. Gates, A. J. P. White, M. R. Crimmin, Angew. Chem. Int. Ed., 2012, 51, 12559-12563.
[62]	A. Masarwa, D. Didier, T. Zabrodski, M. Schinkel, L. Ackermann, I. Marek, Nature, 2013, 505, 199.
[63]	Y.-Q. Zhang, E. Vogelsang, Z.-W Qu, S. Grimme, A. Gansäuer, Angew. Chem. Int. Ed., 2017, 56, 12654-12657.
[64]	C. Yao, T. Dahmen, A. Gansäuer, J. Norton, Science, 2019, 364, 764-767.
[65]	F. Reiss, M. Reiss, J. Bresien, A. Spannenberg, H. Jiao, W. Baumann, P. Arndt, T. Beweries, Chem. Sci., 2019, 10, 5319-5325.
[66]	J. Weweler, S. L. Younas, J. Streuff, Angew. Chem. Int. Ed., 2019, 58, 17700-17703.
[67]	Z. Zhang, T. Hilche, D. Slak, N. R. Rietdijk, U. N. Oloyede, R. A. Flowers, A. Gansäuer, Angew. Chem. Int. Ed., 2020, 59, 9355-9359.
[68]	U. Rosenthal, Chem. Soc. Rev., 2020, 49, 2119-2139.
[69]	C. Matt, C. Kern, J. Streuff, ACS Catal., 2020, 10, 6409-6413.
[70]	M. Manssen, L. L. Schafer, Chem. Soc. Rev., 2020, 49, 6947-6994.
[71]	E. N. Bahena, S. E. Griffin, L. L. Schafer, J. Am. Chem. Soc., 2020, 142, 20566-20571.
[72]	X. Yan, C. Xi, Coord. Chem. Rev., 2016, 308, 22-31.
[73]	S. Pereira, M. Srebnik, Organometallics, 1995, 14, 3127-3128.
[74]	S. Pereira, M. Srebnik, J. Am. Chem. Soc., 1996, 118, 909-910.
[75]	X. Shi, S. Li, L. Wu, Angew. Chem. Int. Ed., 2019, 58, 16167-16171.
[76]	X. Wang, X. Cui, S. Li, Y. Wang, C. Xia, H. Jiao, L. Wu, Angew. Chem. Int. Ed., 2020, 59, 13608-13612.
[77]	K.-J. Xiao, J.-M Luo, K.-Y Ye, Y. Wang, P.-Q Huang, Angew. Chem. Int. Ed., 2010, 49, 3037-3040.
[78]	P.-Q. Huang, H. Geng, Org. Chem. Front., 2015, 2, 150-158.
[79]	M. L. Shegavi, S. K. Bose, Catal. Sci. Technol., 2019, 9, 3307-3336.
[80]	K. A. Erickson, M. P. Cibuzar, N. T. Mucha, R. Waterman, Dalton Trans., 2018, 47, 2138-2142.
[81]	J. D. Erickson, T. Y. Lai, D. J. Liptrot, M. M. Olmstead, P. P. Power, Chem. Commun., 2016, 52, 13656-13659.
[82]	E. A. Romero, J. L. Peltier, R. Jazzar, G. Bertrand, Chem. Commun., 2016, 52, 10563-10565.

锆氢催化的酰胺硼氢化合成胺类化合物研究: 机理、使用范围和应用

Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application

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