SynOpen, Table of Contents CC BY ND NC 4.0 · SynOpen 2018; 02(02): 0096-0104DOI: 10.1055/s-0037-1609449 review Copyright with the author Methods for Arylethylation of Amines and Heteroarenes Franz Bracher * Department of Pharmacy – Center for Drug Research, Ludwig-Maximilians University, Butenandtstr. 5-13, 81377 Munich, Germany Email: Franz.Bracher@cup.uni-muenchen.de › Author Affiliations Recommend Article Abstract All articles of this category Dedicated to my friend Norbert Breitschaft, who died on 7th of February, 2018. Abstract Compared with standard N-methylation, benzylation, and alkylation of amines and N-heterocycles, N-arylethylation is significantly more challenging. In this Review the available methods for N-arylethylation are summarized, with a special focus on efficiency, selectivity, availability of the required building blocks, and ecological aspects. Key words Key wordsarylethylation - phenethylation - alkylation - reductive amination - hydroamination - reduction Full Text References References 1 Manallack DT. Prankerd RJ. Yuriev E. Oprea TI. Chalmers DK. Chem. Soc. Rev. 2013; 42: 485 2 Dong H. Latka RT. Driver TG. Org. Lett. 2011; 13: 2726 3 Wekesa FS. Phadke N. Jahier C. Cordes DB. Findlater M. Synthesis 2014; 46: 1046 4 Ben Haddou T. Béni S. Hosztafi S. Malfacini D. Calo G. Schmidhammer H. Spetea M. PLoS ONE 2014; e99231 5 Lim HJ. Dersch CM. Rothman RB. Deschamps JR. Jacobson AE. Rice KC. Eur. J. Med. Chem. 2013; 67: 335 6 Hutchison AJ. de Jesus R. Williams M. Simke JP. Neale RF. Jackson RH. Ambrose F. Barbaz BJ. Sills MA. J. Med. Chem. 1989; 32: 2221 7 Ivachtchenko AV. Frolov EB. Mitkin OD. Tkachenko SE. Okun IM. Khvat AV. Bioorg. Med. Chem. Lett. 2010; 20: 78 8 Mokrosz JL. Bojarski AJ. Charakchieva-Minol S. Duszynska B. Mokrosz MJ. Paluchowska MH. Arch. Pharm. (Weinheim) 1995; 328: 604 9 Birnbaum LS. Powell G. J. Am. Chem. Soc. 1945; 67: 1464 10 Forrest J. Liddell DA. Tucker SH. J. Chem. Soc. 1946; 454 11 Albright JD. DeVries VG. Largis EE. Miner TG. Reich MF. Schaffer SA. Shepherd RG. Upeslacis J. J. Med. Chem. 1983; 26: 1378 12 Romera JL. Cid JM. Trabanco AA. Tetrahedron Lett. 2004; 45: 8797 13 Sato K. Takahagi H. Yoshikawa T. Morimoto S. Takai T. Hidaka K. Kamaura M. Kubo O. Adachi R. Ishii T. Maki T. Mochida T. Takekawa S. Nakakariya M. Amano N. Kitazaki T. J. Med. Chem. 2015; 58: 3892 14 Tsotinis A. Vlachou M. Eleutheriades A. Prinea E. Ebreo D. The M.-T. Sugden D. Chem. Pharm. Bull. 2002; 50: 31 15 Eisch JJ. Dua SK. Kovacs CA. J. Org. Chem. 1987; 52: 4437 16 Otto R. Penzis R. Gaube F. Winckler T. Appenroth D. Fleck C. Tränkle C. Lehmann J. Enzensperger C. Eur. J. Med. Chem. 2014; 87: 63 17 Rupčić R. Modrić M. Hutinec A. Čikoš A. Stanić B. Mesić M. Pešić D. Merćep M. J. Heterocycl. Chem. 2010; 47: 640 18 Clarke D. Gilbert BC. Hanson P. Kirk CM. J. Chem. Soc., Perkin Trans. 2 1978; 1103 19 Larrosa M. Guerrero C. Rodríguez R. Cruces J. Synlett 2010; 2101 20 Black LA. Nersesian DL. Sharma P. Ku Y.-Y. Bennani YL. Marsh KC. Miller TR. Esbenshade TA. Hancock AA. Cowart M. Bioorg. Med. Chem. Lett. 2007; 17: 1443 21 Rueter JK. Nortey SO. Baxter EW. Leo GC. Reitz AB. Tetrahedron Lett. 1998; 39: 975 22 Zhao L. Cao D. Chen T. Wang Y. Miao Z. Xu Y. Chen W. Wang X. Li Y. Du Z. Xiong B. Li J. Xu C. Zhang N. He J. Shen J. J. Med. Chem. 2013; 56: 3833 23 Li A. Mishra Y. Malik M. Wang Q. Li S. Taylor M. Reichert DE. Luedtke RR. Mach RH. Bioorg. Med. Chem. 2013; 21: 2988 24 Yakabe S. Synth. Commun. 2010; 40: 1339 25 Levi L. Scheuren S. Müller TJ. J. Synthesis 2014; 46: 3059 26 Iranpoor N. Firouzabadi H. Nowrouzi N. Khalili D. Tetrahedron 2009; 65: 3893 27 Kawahara R. Fujita K.-i. Yamaguchi R. Adv. Synth. Catal. 2011; 353: 1161 28 Mehta A. Thaker A. Londhe V. Nandan SR. Appl. Catal., A: General 2014; 478: 241 29 Hamid MH. S. A. Williams JM. J. Chem. Commun. 2007; 725 30 Cui X. Dai X. Deng Y. Shi F. Chem. Eur. J. 2013; 19: 3665 31 Wu K. He W. Sun C. Yu Z. Tetrahedron 2016; 72: 8516 32 Mamidala R. Mukundam V. Dhanunjayarao K. Venkatasubbaiah K. Tetrahedron 2017; 73: 2225 33 Yin Z. Zeng H. Wu J. Zheng S. Zhang G. ACS Catal. 2016; 6: 6546 34 Hollmann D. Bähn S. Tillack A. Beller M. Angew. Chem. Int. Ed. 2007; 46: 8291 35 Linciano P. Pizzetti M. Porcheddu A. Taddei M. Synlett 2013; 24: 2249 36 Mori-Quiroz LM. Shimkin KW. Rezazadeh S. Kozlowski RA. Watson DA. Chem. Eur. J. 2016; 22: 15654 37 Rossi SA. Shimkin KW. Xu Q. Mori-Quiroz LM. Watson DA. Org. Lett. 2013; 15: 2314 38 Josyula KV. B. Gao P. Hewitt C. Tetrahedron Lett. 2003; 44: 7789 39 Naya L. Larrosa M. Rodríguez R. Cruces J. Tetrahedron Lett. 2012; 53: 769 40 Barton DH. R. Ozbalik N. Ramesh M. Tetrahedron Lett. 1988; 29: 857 41 Selvakumar K. Rangareddy K. Harrod JF. Can. J. Chem. 2004; 82: 1244 42 Dittrich-Wengenroth E. Siegel S. Woltering M. PCT Int. Appl. WO2005019169 A2, 2005 43 Pelletier G. Bechara WS. Charette AB. J. Am. Chem. Soc. 2010; 132: 12817 44 Neumann W. Frank R. Hey Hawkins E. Dalton Trans. 2015; 1748 45 Song B. Rudolphi F. Himmler T. Gooßen LJ. Adv. Synth. Catal. 2011; 353: 1565 46 Sorribes I. Cabrero-Antonino JR. Vicent C. Junge K. Beller M. J. Am. Chem. Soc. 2015; 137: 13580 47 Adam R. Cabrero-Antonino JR. Junge K. Jackstell R. Beller M. Angew. Chem. 2016; 128: 11215 48 Sorribes I. Junge K. Beller M. J. Am. Chem. Soc. 2014; 136: 14314 49 Eggler JF. Holland GF. Johnson MR. Volkmann RA. U. S. US 4738972A, 1988 50 Parlow JJ. Stevens AM. Stegeman RA. Stallings WC. Kurumbail RG. South MS. J. Med. Chem. 2003; 46: 4297 51 Long K. Edwards TA. Wilson AJ. Bioorg. Med. Chem. 2013; 21: 4034 52 Shibata I. Suwa T. Sugiyama E. Baba A. Synlett 1998; 1081 53 Suwa T. Sugiyama E. Shibata I. Baba A. Synthesis 2000; 789 54 Kumar R. Gravel E. Hagège A. Li H. Verma D. Namboothiri IN. N. Doris E. ChemCatChem 2013; 5: 3571 55 Zhu M. Catal. Lett. 2014; 144: 1568 56 Zhang X.-L. Yu P. Wu Y.-W. Wu Q.-P. Zhang Q.-S. J. Chem. Res. 2014; 38: 261 57 Vögerl K. Ong DN. Bracher F. Synthesis 2018; 50: 1323 58 Tiddens MR. Klein Gebbink RJ. M. Otte M. Org. Lett. 2016; 18: 3714 59 Shao Z. Fu S. Wei M. Zhou S. Liu Q. Angew. Chem. Int. Ed. 2016; 55: 14653 60 Sajiki H. Ikawa T. Hirota K. Org. Lett. 2004; 6: 4977 61 Kindler K. Schrader K. Middelhoff B. Arch. Pharm. 1950; 283: 184 62 Ikawa T. Fujita Y. Mizusaki T. Betsuin S. Takamatsu H. Maegawa T. Monguchi Y. Sajiki H. Org. Biomol. Chem. 2012; 10: 293 63 Müller TE. Beller M. Chem. Rev. 1998; 98: 675 64 Müller TE. Hultzsch KC. Yus M. Foubelo F. Tada M. Chem. Rev. 2008; 108: 3795 65 Huang L. Arndt M. Gooßen K. Heydt H. Gooßen LJ. Chem. Rev. 2015; 115: 2596 66 Munro-Leighton C. Delp SA. Alsop NM. Blue ED. Gunnoe TB. Chem. Commun. 2008; 111 67 Beller M. Breindl C. Riermeier TH. Tillack A. J. Org. Chem. 2001; 66: 1403 68 Kumar K. Michalik D. Castro IG. Tillack A. Zapf A. Arlt M. Heinrich T. Böttcher H. Beller M. Chem. Eur. J. 2004; 10: 746 69 Beller M. Breindl C. Riermeier TH. Eichberger M. Trauthwein H. Angew. Chem. Int. Ed. 1998; 37: 3389 70 Seijas JA. Vázquez-Tato MP. Martínez MM. Synlett 2001; 875 71 Schlott RJ. Falk JC. Narducy KW. J. Org. Chem. 1972; 37: 4243 72 Seijas JA. Vázquez-Tato MP. Entenza C. Martínez MM. Ónega MG. Veiga S. Tetrahedron Lett. 1998; 39: 5073 73 Jaspers D. Doye S. Synlett 2011; 1444 74 Tzalis D. Koradin C. Knochel P. Tetrahedron Lett. 1999; 40: 6193 75 Ivachtchenko AV. Frolov EB. Mitkin OD. Kysil VM. Khvat AV. Okun IM. Tkachenko SE. Bioorg. Med. Chem. Lett. 2009; 19: 3183 76 Severin R. Doye S. Chem. Soc. Rev. 2007; 36: 1407 77 Lui EK. J. Schafer LL. Adv. Synth. Catal. 2016; 358: 713 78 Heutling A. Pohlki F. Bytschkov I. Doye S. Angew. Chem. Int. Ed. 2005; 44: 2951 79 Katritzky AR. Strah S. Belyakov SA. Tetrahedron 1998; 54: 7167 80 Katritzky AR. Shobana N. Harris PA. Tetrahedron Lett. 1991; 32: 4247 81 Werner V. Ellwart M. Wagner AJ. Knochel P. Org. Lett. 2015; 17: 2026 82 Katritzky AR. Sączewski F. Marson CM. J. Org. Chem. 1985; 50: 1351