Highly selective partial dehydrogenation of tetrahydroisoquinolines using modified Pd/C

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

Abstract

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

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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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60243-6

https://www.cjcatal.com/EN/Y2015/V36/I1/33

References

[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