Synthesis of 4-Alkylidene-Substituted 1,2,3,4-Tetrahydroisoquinolines via Palladium-Catalyzed Carbopalladation/C–H Activation of 2-Bromobenzyl-N-propargylamines

Abstract

Tetrasubstituted alkene-based 1,2,3,4-tetrahydroisoquinolines are synthesized via the formation of a cyclic carbopalladation complex followed by C–H bond activation of the sp² carbon in arenes. This domino reaction proceeds with good selectivity and provides good yields of the products. The requisite starting materials are synthesized by copper(I) iodide catalyzed A³-coupling reactions.

Key words

palladium - C–H activation - alkynes - heterocycles - carbo­palladation

• References

• 1a Tietze LF. Chem. Rev. 1996; 96: 115
• 1b Zeni G, Larock RC. Chem. Rev. 2006; 106: 4644
• 1c Chernyak D, Gevorgyan V. Org. Lett. 2010; 12: 5558
• 1d Yamamoto Y. Chem. Soc. Rev. 2014; 43: 1575
• 2a Negishi E.-i, Copéret C, Ma S, Liou S.-Y, Liu F. Chem. Rev. 1996; 96: 365
• 2b Ma S, Xu B. J. Org. Chem. 1998; 63: 9156
• 2c Rivera-Fuentes P, von Wantoch Rekowski M, Schweizer WB, Gisselbrecht J.-P, Boudon C, Diederich F. Org. Lett. 2012; 14: 4066
• 2d Chinchilla R, Najera C. Chem. Rev. 2014; 114: 1783
• 2e Beccalli EM, Broggini G, Gazzola S, Mazza A. Org. Biomol. Chem. 2014; 12: 6767
• 3a Grigg R, Loganathan V, Sridharan V. Tetrahedron Lett. 1996; 37: 3399
• 3b Ohno H, Yamamoto M, Iuchi M, Tanaka T. Angew. Chem. Int. Ed. 2005; 44: 5103 ; Angew. Chem. 2005, 117, 5233
• 3c Yu JQ, Giri R, Chen X. Org. Biomol. Chem. 2006; 4: 4041
• 3d Wencel-Delord J, Droge T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740
• 3e Ohno H, Yamamoto M, Iuchi M, Fujii N, Tanaka T. Synthesis 2011; 2567
• 3f Zou T, Zhang X.-G, Li J.-H, Deng C.-L, Tang R.-Y. Adv. Synth. Catal. 2012; 354: 889
• 3g Tietze LF, Hungerland T, Depken T, Maaß C, Stalke D. Synlett 2012; 23: 2516
• 3h Leibeling M, Pawliczek M, Kratzert D, Stalke D, Werz DB. Org. Lett. 2012; 14: 346
• 3i Wallbaum J, Neufeld R, Stalke D, Werz DB. Angew. Chem. Int. Ed. 2013; 52: 13243 ; Angew. Chem. 2013, 125, 13485
• 4a Sigman MS, Schultz MJ. Org. Biomol. Chem. 2004; 2: 2551
• 4b Kotov V, Scarborough CC, Stahl SS. Inorg. Chem. 2007; 46: 1910
• 4c Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
• 4d Le Bras J, Muzart J. Chem. Rev. 2011; 111: 1170
• 4e Neufeldt SR, Sanford MS. Acc. Chem. Res. 2012; 45: 936
• 4f Broggini G, Beccalli EM, Fasana A, Gazzola S. Beilstein J. Org. Chem. 2012; 8: 1730
• 4g Tietze LF, Hungerland T, Düfert A, Objartel I, Stalke D. Chem. Eur. J. 2012; 18: 3286
• 5a Tietze LF, Lotz F. Eur. J. Org. Chem. 2006; 4676
• 5b Gericke KM, Chai DI, Bieler N, Lautens M. Angew. Chem. Int. Ed. 2009; 48: 1447; Angew. Chem. 2009, 121, 1475
• 5c Tietze LF, Hungerland T, Depken C, Maaß C, Stalke D. Synlett 2012; 23: 2516
• 6 Phillipson JD, Roberts MF, Zenk MH. The Chemistry and Biology of Isoquinoline Alkaloids . Springer; Berlin: 1985
• 7 Bentley KW. Nat. Prod. Rep. 2006; 23: 444
• 8a Scott JD, Williams RM. J. Am. Chem. Soc. 2002; 124: 2951
• 8b Magnus P, Matthews KS, Lynch V. Org. Lett. 2003; 5: 2181
• 8c Kwon S, Myers AG. J. Am. Chem. Soc. 2005; 127: 16796
• 8d Magnus P, Matthews KS. J. Am. Chem. Soc. 2005; 127: 12476
• 8e Chen J, Chen X, Bois-Choussy M, Zhu J. J. Am. Chem. Soc. 2006; 128: 87
• 9 Mueller S, Herzog B, Quass K. WO2006034968, 2006
• 10 Britten NJ, Burns JW, Hallberg JW, Waldron NA, Watts JL. WO2004082588, 2004
• 11a Thangthong AM, Prachumrak N, Namuangruk S, Jungsuttiwong S, Keawin T, Sudyoadsuk T, Promarak V. Eur. J. Org. Chem. 2012; 5263
• 11b Baheti A, Thomas KR. J, Lee C.-P, Li C.-T, Ho K.-C. J. Mater. Chem. A 2014; 2: 5766
• 12a Robertson DW, Katzenellenbogen JA, Hayes JR, Katzenellenbogen BS. J. Med. Chem. 1982; 25: 167 ; and references therein
• 12b McKinley NF, O’Shea DF. J. Org. Chem. 2006; 71: 9552
• 12c Shimizu K, Takimoto M, Mori M, Sato Y. Synlett 2006; 3182
• 13a Caturla F, Amat M, Reinoso RF, Cordoba M, Warrellow G. Bioorg. Med. Chem. Lett. 2006; 16: 3209
• 13b Wadman M. Nature 2006; 440: 277
• 14 Yu H, Richey RN, Carson MW, Coghlan MJ. Org. Lett. 2006; 8: 1685
• 15a Koumura N, Zijlstra RW. J, van Delden RA, Harada N, Feringa BL. Nature 1999; 401: 152
• 15b Feringa BL, van Delden RA, Koumura N, Geertsema EM. Chem. Rev. 2000; 100: 1789
• 15c Koumura N, Geertsema EM, van Gelder MB, Meetsma A, Feringa BL. J. Am. Chem. Soc. 2002; 124: 5037
• 16a ter Wiel MK. J, van Delden RA, Meetsma A, Feringa BL. J. Am. Chem. Soc. 2003; 125: 15076
• 16b Vicario J, Meetsma A, Feringa BL. Chem. Commun. 2005; 5910
• 16c Vicario J, Walko M, Meetsma A, Feringa BL. J. Am. Chem. Soc. 2006; 128: 5127
• 17a Nandakumar A, Perumal PT. Org Lett. 2013; 15: 382
• 17b Naveen K, Muralidharan D, Perumal PT. Eur. J. Org. Chem. 2014; 1172