Pd/C促进的四氢异喹啉高选择性部分脱氢

doi:10.1016/S1872-2067(14)60243-6

催化学报 ›› 2015, Vol. 36 ›› Issue (1): 33-39.DOI: 10.1016/S1872-2067(14)60243-6

Pd/C促进的四氢异喹啉高选择性部分脱氢

姬悦^a, 陈木旺^a, 时磊^a,b, 周永贵^a

a 中国科学院大连化学物理研究所, 辽宁大连116023;
b 大连理工大学精细化工国家重点实验室, 辽宁大连116024

收稿日期:2014-10-01 修回日期:2014-11-03 出版日期:2014-12-31 发布日期:2014-12-31
通讯作者: 时磊, 周永贵
基金资助:
国家自然科学基金(21202162); 大连理工大学精细化工国家重点实验室开放课题基金(KF1110).

Highly selective partial dehydrogenation of tetrahydroisoquinolines using modified Pd/C

Yue Ji^a, Mu-Wang Chen^a, Lei Shi^a,b, Yong-Gui Zhou^a

a Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;
b State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, Liaoning, China

Received:2014-10-01 Revised:2014-11-03 Online:2014-12-31 Published:2014-12-31
Supported by:
This work was supported by the National Natural Science Foundation of China (21202162) and the State Key Laboratory of Fine Chemicals (KF1110).

摘要/Abstract

摘要：

采用K₃PO₄·3H₂O修饰的Pd/C为催化剂实现了取代四氢异喹啉高选择性部分脱氢, 并成功地避免了当量有害氧化剂的使用. 多相催化剂Pd/C对四氢异喹啉化合物具有催化脱氢活性, 但反应选择性较差, 同时产生完全脱氢的芳构化产物异喹啉. 而K₃PO₄·3H₂O修饰的Pd/C催化剂能有效提高脱氢反应的化学选择性, 在最优条件下可获得最高89%的分离收率. 这为取代3,4-二氢异喹啉的合成提供了一种简便、高原子经济性和高化学选择性的反应途径. 此外, 该多相催化剂可回收循环使用多次, 且活性和选择性基本保持不变.

关键词: 钯碳, 部分脱氢, 四氢异喹啉, 亚胺, 脱氢芳构化

Abstract:

A highly selective procedure has been developed for the partial dehydrogenation of 1-substituted-1,2,3,4-tetrahydroisoquinolines over K₃PO₄·3H₂O-modified Pd/C catalyst. This new method provides facile, atom-economical and environmentally friendly access to 1-substituted-3,4-dihydroisoquinolines without the need for stoichiometric amounts of harmful oxidants. The use of standard Pd/C as a catalyst for this process gave poor chemoselectivity. Pleasingly, the use of a K₃PO₄·3H₂O-modified Pd/C catalyst promoted the partial dehydrogenation of 1-substituted-1,2,3,4-tetrahydroisoquinolines with excellent chemoselectivity by suppressing further dehydroaromatization. Furthermore, conducting the reaction under an atmosphere of oxygen led to further improvements in the chemoselectivity of the dehydrogenation, with the ratio of imine to isoquinoline reaching up to 32/1. The heterogenous Pd/C catalyst could also be recycled and reused at least three times with excellent conversion and chemoselectivity, demonstrating the significantly practical potential of this methodology.

Key words: Palladium on carbon, Partial dehydrogenation, Tetrahydroisoquinoline, Imine, Dehydroaromatization

姬悦, 陈木旺, 时磊, 周永贵. Pd/C促进的四氢异喹啉高选择性部分脱氢[J]. 催化学报, 2015, 36(1): 33-39.

Yue Ji, Mu-Wang Chen, Lei Shi, Yong-Gui Zhou. Highly selective partial dehydrogenation of tetrahydroisoquinolines using modified Pd/C[J]. Chinese Journal of Catalysis, 2015, 36(1): 33-39.

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参考文献

[1] Orito K, Hatakeyama T, Takeo M, Uchiito S, Tokuda M, Suginome H. Tetrahedron, 1998, 54: 8403
[2] Ajzert K I, Takács K. Liebigs Ann Chem, 1987: 1061
[3] Khatri P K, Jain S L, Sivakumar K L N, Sain B. Org Biomol Chem, 2011, 9: 3370
[4] Yao W B, Zhang Y X, Jia X Q, Huang Z. Angew Chem Int Ed, 2014, 53: 1390
[5] Choi H, Doyle M P. Chem Commun, 2007: 745
[6] Goti A, Romani M. Tetrahedron Lett, 1994, 35: 6567
[7] Kamal A, Devaiah V, Reddy K L, Shankaraiah N. Adv Synth Catal, 2006, 348: 249
[8] Chen Y, Crockett R D, Wang X, Larsen R D, Cui S, Faul M M. Synlett, 2013, 24: 301
[9] Aoyama T, Sonoda N, Yamauchi M, Toriyama K, Anzai M, Ando A, Shioiri T. Synlett, 1998, 1: 35
[10] Huang B, Tian H W, Lin S S, Xie M H, Yu X C, Xu Q. Tetrahedron Lett, 2013, 54: 2861
[11] Reyes-Sánchez A, Cañavera-Buelvas F, Barrios-Francisco R, Cifuentes-Vaca O L, Flores-Alamo M, García J J. Organometallics, 2011, 30: 3340
[12] Bolchi C, Pallavicini M, Fumagalli L, Straniero V, Valoti E. Org Process Res Dev, 2013, 17: 432
[13] Scully F E Jr, Schlager J J. Heterocycles, 1982, 19: 653
[14] Choi J, MacArthur A H R, Brookhart M, Goldman A S. Chem Rev, 2011, 111: 1761
[15] Esswein A J, Nocera D G. Chem Rev, 2007, 107: 4022
[16] Zhang W, Ma H, Zhou L P, Miao H, Xu J. Chin J Catal (张伟, 马红, 周利鹏, 苗虹, 徐杰. 催化学报), 2009, 30: 86
[17] Li C G, Miao C X, Nie Y Y, Yue Y H, Gu S Y, Yang W M, Hua W M, Gao Z. Chin J Catal (李春光, 缪长喜, 聂颖颖, 乐英红, 顾松园, 杨为民, 华伟明, 高滋. 催化学报), 2010, 31: 993
[18] Ye X N, Hua W M, Yue Y H, Miao C X, Xie Z K, Gao Z. Chin J Catal (叶兴南, 华伟明, 乐英红, 缪长喜, 谢在库, 高滋. 催化学报), 2004, 25: 581
[19] Jin M, Cheng Z M, Jiang X X, Gao Y L, Fang X C. Chin J Catal (晋梅, 程振民, 江晓霞, 高玉兰, 方向晨. 催化学报), 2010, 31: 1177
[20] Dobereiner G E, Crabtree R H. Chem Rev, 2010, 110: 681
[21] Schümperli M T, Hammond C, Hermans I. ACS Catal, 2012, 2:1108
[22] Largeron M. Eur J Org Chem, 2013: 5225
[23] Patil R D, Adimurthy S. Asian J Org Chem, 2013, 2: 726
[24] Angelici R J. Catal Sci Technol, 2013, 3: 279
[25] Turner N J. Chem Rev, 2011, 111: 4073
[26] Li Z C, Chen C H, Zhan E S, Ta N, Shen W J. Catal Commun, 2014, 51: 58
[27] Li Z C, Chen C H, Zhan E S, Ta N, Li Y, Shen W J. Chem Commun, 2014, 50: 4469
[28] Li Z C, Li Y, Zhan E S, Ta N, Shen W J. J Mater Chem A, 2013, 1: 15370
[29] Shi Q J, Liu N, Liang Y. Chin J Catal (石秋杰, 刘宁, 梁义. 催化学报), 2007, 28: 57
[30] Chen J, Zhang Q H, Fang W H, Wang Y, Wan H L. Chin J Catal (陈静, 张庆红, 方文浩, 王野, 万惠霖. 催化学报), 2010, 31: 1061
[31] Wang F, Shi R J, Liu Z Q, Shang P J, Pang X Y, Shen S, Feng Z C, Li C, Shen W J. ACS Catal, 2013, 3: 890
[32] Adkins H, Lundsted L G. J Am Chem Soc, 1949, 71: 2964
[33] Angelici R J. J Organomet Chem, 2008, 693: 847
[34] Jin X K, Liu Y X, Lu Q Q, Yang D Y, Sun J K, Qin S S, Zhang J W, Shen J X, Chu C H, Liu R H. Org Biomol Chem, 2013, 11: 3776
[35] Gu X Q, Chen W, Morales-Morales D, Jensen C M. J Mol Catal A, 2002, 189: 119
[36] Lu S M, Wang Y Q, Han X W, Zhou Y G. Chin J Catal (卢胜梅, 汪游清, 韩秀文, 周永贵. 催化学报), 2005, 26: 287
[37] Wang D W, Wang X B, Wang D S, Lu S M, Zhou Y G, Li Y X. J Org Chem, 2009, 74: 2780
[38] Yamaguchi R, Ikeda C, Takahashi Y, Fujita K I. J Am Chem Soc, 2009, 131: 8410
[39] Wu J J, Talwar D, Johnston S, Yan M, Xiao J L. Angew Chem Int Ed, 2013, 52: 6983
[40] Fujita K I, Tanaka Y, Kobayashi M, Yamaguchi R. J Am Chem Soc, 2014, 136: 4829
[41] Yi C S, Lee D W. Organometallics, 2009, 28: 947
[42] Wendlandt A E, Stahl S S. J Am Chem Soc, 2014, 136: 11910
[43] Hara T, Mori K, Mizugaki T, Ebitani K, Kaneda K. Tetrahedron Lett, 2003, 44: 6207
[44] Dean D, Davis B, Jessop P G. New J Chem, 2011, 35: 417
[45] Chakraborty S, Brennessel W W, Jones W D. J Am Chem Soc, 2014, 136: 8564
[46] Luca O R, Huang D L, Takase M K, Crabtree R H. New J Chem, 2013, 37: 3402
[47] Zhang D, Wu L Z, Zhou L, Han X, Yang Q Z, Zhang L P, Tung C H. J Am Chem Soc, 2004, 126: 3440
[48] Li H, Jiang J, Lu G, Huang F, Wang Z X. Organometallics, 2011, 30: 3131
[49] Zhang X B, Xi Z. Phys Chem Chem Phys, 2011, 13: 3997
[50] Wendlandt A E, Stahl S S. J Am Chem Soc, 2014, 136: 506
[51] Ghislieri D, Green A P, Pontini M, Willies S C, Rowles I, Frank A, Grogan G, Turner N J. J Am Chem Soc, 2013, 135: 10863
[52] Sonobe T, Oisaki K, Kanai M. Chem Sci, 2012, 3: 3249
[53] Ru?i M, Pe?avar A, Prudi? D, Kralj D, Scriban C, Antonio Z G. Org Process Res Dev, 2012, 16: 1293
[54] Chang M X, Li W, Zhang X M. Angew Chem Int Ed, 2011, 50: 10679
[55] Dong J, Shi X X, Yan J J, Xing J, Zhang Q, Xiao S. Eur J Org Chem, 2010: 698
[56] Berhal F, Wu Z, Zhang Z G, Ayad T, Ratovelomanana-Vidal V. Org Lett, 2012, 14: 3308
[57] Romines K R, Freeman G A, Schaller L T, Cowan J R, Gonzales S S, Tidwell J H, Andrews III C W, Stammers D K, Hazen R J, Ferris R G, Short S A, Chan J H, Boone L R. J Med Chem, 2006, 49: 727
[58] Dong J, Shi X X, Xing J, Yan J J. Synth Commun, 2012, 42: 2806
[59] Jin Q R, Jia G Q, Zhang Y M, Li C. Catal Sci Technol, 2014, 4: 464

Pd/C促进的四氢异喹啉高选择性部分脱氢

Highly selective partial dehydrogenation of tetrahydroisoquinolines using modified Pd/C

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