CC BY-ND-NC 4.0 · SynOpen 2018; 02(02): 0096-0104
DOI: 10.1055/s-0037-1609449
review
Copyright with the author

Methods for Arylethylation of Amines and Heteroarenes

Department of Pharmacy – Center for Drug Research, Ludwig-Maximilians University, Butenandtstr. 5-13, 81377 Munich, Germany   eMail: Franz.Bracher@cup.uni-muenchen.de
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Publikationsverlauf

Received: 21. Februar 2018

Accepted: 18. März 2018

Publikationsdatum:
03. April 2018 (online)


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.

 
  • 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