Oxidative Allylic Amination Reactions of Unactivated Olefins – At the Frontiers of Palladium and Selenium Catalysis

Abstract

The direct oxidative conversion of simple, nonactivated alkenes into allylic amine derivatives represents a profound challenge to contemporary chemical synthesis. This article provides an overview on recent methodological developments and applications in the realm of modern palladium- and selenium-catalyzed oxidative allylic amination reactions.

Key words

alkenes - oxidation - C–N bond construction - transition metals - chalcogens - catalysis

• References

• 1 Hili R, Yudin AK. Nat. Chem. Biol. 2006; 2: 284
• 2 Amino Group Chemistry: From Synthesis to the Life Sciences. Ricci A. Wiley-VCH; Weinheim: 2008

For selected review articles, see:
• 3a Nishina N, Yamamoto Y. Top. Organomet. Chem. 2013; 43: 115
• 3b Patil NT, Kavthe RD, Shinde VS. Tetrahedron 2012; 68: 8079
• 3c Müller TE, Hultzsch KC, Yus M, Foubelo F, Tada M. Chem. Rev. 2008; 108: 3795
• 3d Aillaud I, Collin J, Hannedouche J, Schulz E. Dalton Trans. 2007; 5105
• 3e Hultzsch KC. Adv. Synth. Catal. 2005; 347: 367
• 3f Hartwig JF. Pure Appl. Chem. 2004; 76: 507
• 3g Hong S, Marks TJ. Acc. Chem. Res. 2004; 37: 673
• 3h Müller TE, Beller M. Chem. Rev. 1998; 98: 675

For selected review articles on C–H nitrogenations, see:
• 4a Ramirez TA, Zhao B, Shi Y. Chem. Soc. Rev. 2012; 41: 931
• 4b McDonald RI, Liu G, Stahl SS. Chem. Rev. 2011; 111: 2981
• 4c Zalatan DN, DuBois J. Top. Curr. Chem. 2010; 292: 347
• 4d Davies HM. L, Manning JR. Nature (London) 2008; 451: 417
• 4e Davies HM. L, Long MS. Angew. Chem. Int. Ed. 2005; 44: 3518
• 4f Müller P, Fruit C. Chem. Rev. 2003; 103: 2905

For selected review articles, see:
• 5a Sundararaju B, Achard M, Bruneau C. Chem. Soc. Rev. 2012; 41: 4467
• 5b Lu Z, Ma S. Angew. Chem. Int. Ed. 2008; 47: 258
• 5c Trost BM, Crawley ML. Chem. Rev. 2003; 103: 2921
• 5d Trost BM. Chem. Pharm. Bull. 2002; 50: 1
• 5e Johannsen M, Jørgensen KA. Chem. Rev. 1998; 98: 1689
• 5f Trost BM, Van Vraken DL. Chem. Rev. 1996; 96: 395
• 6a Beletskaya IP, Cheprakov AV. Organometallics 2012; 31: 7753
• 6b Barluenga J, Valdés C. Chem. Commun. 2005; 4891
• 6c Barluenga J, Fernández MA, Aznar F, Valdés C. Chem. Commun. 2002; 2362
• 6d Kozawa Y, Mori M. Tetrahedron Lett. 2002; 43: 111
• 7a Wender PA, Miller BL. Nature (London) 2009; 460: 197
• 7b Wender PA, Verma VA, Paxton TJ, Pillow TH. Acc. Chem. Res. 2008; 41: 40
• 7c Wender PA, Croatt MP, Witulski B. Tetrahedron 2006; 62: 7505
• 8a Trenner J, Depken C, Weber TJ, Breder A. Angew. Chem. Int. Ed. 2013; 52: 8952
• 8b Chen F, Tan CK, Yeung Y.-Y. J. Am. Chem. Soc. 2013; 135: 1232
• 8c Souto JA, Zian D, Muñiz K. J. Am. Chem. Soc. 2012; 134: 7242
• 8d Souto JA, Becker P, Iglesias Á, Muñiz K. J. Am. Chem. Soc. 2012; 134: 15505
• 8e Souto JA, Becker PÁ, Muñiz K. J. Am. Chem. Soc. 2012; 134: 15505
• 9a Lafrance M, Roggen M, Carreira EM. Angew. Chem. Int. Ed. 2012; 51: 3470
• 9b Hartwig JF, Stanley LM. Acc. Chem. Res. 2010; 43: 1461
• 9c Trost BM, Zhang T, Sieber JD. Chem. Sci. 2010; 1: 427
• 9d Johannsen M, Jørgensen KA. Chem. Rev. 1998; 98: 1689
• 10 Fix SR, Brice JL, Stahl SS. Angew. Chem. Int. Ed. 2002; 41: 164
• 11a Larock RC, Hightower TR, Hasvold LA, Peterson KP. J. Org. Chem. 1996; 61: 3584
• 11b Rönn M, Bäckvall J.-E, Andersson PG. Tetrahedron Lett. 1995; 36: 7749
• 11c van Benthem RA. T. M, Hiemstra H, Longarela GR, Speckamp WN. Tetrahedron Lett. 1994; 35: 9281
• 12a Ye X, White PB, Stahl SS. J. Org. Chem. 2013; 78: 2083
• 12b Ye X, Liu G, Popp BV, Stahl SS. J. Org. Chem. 2011; 76: 1031
• 12c Popp BV, Stahl SS. Chem. Eur. J. 2009; 15: 2915

For an example of an NHC ligand, see:
• 12d Rogers MM, Wendlandt JE, Guzei IA, Stahl SS. Org. Lett. 2006; 8: 2257
• 13 Beccalli EM, Broggini G, Paladino G, Penoni A, Zoni C. J. Org. Chem. 2004; 69: 5627
• 14 Wu L, Qiu S, Liu G. Org. Lett. 2009; 11: 2707
• 15 Yang G, Zhang W. Org. Lett. 2012; 14: 268
• 16a Ye X, White PB, Stahl SS. J. Org. Chem. 2013; 78: 2083
• 16b Weinstein AB, Stahl SS. Angew. Chem. Int. Ed. 2012; 51: 11505
• 16c Yang G, Shen C, Zhang W. Angew. Chem. Int. Ed. 2012; 51: 9141
• 16d McDonald RI, White PB, Weinstein AB, Tam CP, Stahl SS. Org. Lett. 2011; 13: 2830
• 16e Jiang F, Wu Z, Zhang W. Tetrahedron Lett. 2010; 51: 5124
• 16f Scarborough CC, Bergant A, Sazama GT, Guzei IA, Spencer LC, Stahl SS. Tetrahedron 2009; 65: 5084
• 17a Rice GT, White MC. J. Am. Chem. Soc. 2009; 131: 11701
• 17b Reed SA, White MC. J. Am. Chem. Soc. 2008; 130: 3316
• 17c Fraunhoffer KJ, White MC. J. Am. Chem. Soc. 2007; 129: 7274
• 18 Liu G, Yin G, Wu Y. Angew. Chem. Int. Ed. 2009; 47: 4733
• 19 Yin G, Wu Y, Liu G. J. Am. Chem. Soc. 2010; 132: 11978
• 20 Xiong T, Li Y, Mao L, Zhang Q, Zhang Q. Chem. Commun. 2012; 48: 2246

For reviews, see:
• 21a Song W, Kuzhushkov SI, Ackermann L. Angew. Chem. Int. Ed. 2013; 52: 6576
• 21b Ngatimin M, Lupton DW. Aust. J. Chem. 2010; 63: 653
• 21c Dohi T, Kita Y. Chem. Commun. 2009; 2073
• 21d Uyanik M, Ishihara K. Chem. Commun. 2009; 2086
• 21e Zhdankin VV. ARKIVOC 2009; (i): 1
• 21f Hypervalent Iodine in Organic Chemistry: Chemical Transformations . Moriarty RM, Prakash O. Wiley-Interscience; New York: 2008
• 21g Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
• 21h Ciufolini MA, Braun NA, Canesi S, Ousmer M, Chang J, Chai D. Synthesis 2007; 3759
• 21i Ochiai M. Chem. Rec. 2007; 7: 12
• 21j Top. Curr. Chem. . Wirth T. Springer; Berlin: 2003: 224
• 21k Zhdankin VV, Stang PJ. Chem. Rev. 2002; 102: 2523
• 21l Koser GF. Top. Curr. Chem. 2000; 208: 137
• 21m Stang PJ, Zhdankin VV. Chem. Rev. 1996; 96: 1123
• 22a Samanta R, Lategahn J, Antonchick AP. Chem. Commun. 2012; 48: 3194
• 22b Kantak AA, Potavathri SR, Barham A, Romano KM, DeBoef B. J. Am. Chem. Soc. 2011; 133: 19960
• 22c Antonchick AP, Samanta R, Kulikov K, Lategahn J. Angew. Chem. Int. Ed. 2011; 50: 8605
• 22d Cho SH, Yoo J, Chang S. J. Am. Chem. Soc. 2011; 133: 5996
• 22e Kim HJ, Kim J, Cho SH, Chang S. J. Am. Chem. Soc. 2011; 133: 16382
• 23 Sharpless KB, Hori T, Truesdale LK, Dietrich CO. J. Am. Chem. Soc. 1976; 98: 269
• 24a Kurose N, Takahashi T, Koizumi T. J. Org. Chem. 1996; 61: 2932

For representative racemic variants of this approach, see:
• 24b Spaltenstein A, Carpino PA, Hopkins PB. Tetrahedron Lett. 1986; 27: 147
• 24c Shea RG, Fitzner JN, Fankhauser JE, Spaltenstein A, Carpino PA, Peevey RM, Pratt DV, Tenge BJ, Hopkins PB. J. Org. Chem. 1986; 51: 5243
• 24d Fankhauser JE, Peevey RM, Hopkins PB. Tetrahedron Lett. 1984; 25: 15
• 25a Tiecco M, Testaferri L, Santi C, Tomassini C, Marini F, Bagnoli L, Temperini A. Angew. Chem. Int. Ed. 2003; 42: 3131
• 25b Tiecco M, Testaferri L, Santi C, Tomassini C, Marini F, Bagnoli L, Temperini A. Eur. J. Org. Chem. 2000; 3451
• 25c Hassner A, Amarasekara AS. Tetrahedron Lett. 1987; 28: 5185
• 25d Denis JN, Vicens J, Krief A. Tetrahedron Lett. 1979; 20: 2697

For recent selected examples of pharmacological studies on γ⁴-amino acids, see:
• 26a Clerc J, Groll M, Illich DJ, Bachmann AS, Huber R, Schellenberg B, Dudler R, Kaiser M. Proc. Natl. Acad. Sci. U.S.A. 2009; 106: 6507
• 26b Baldisserotto A, Marastoni M, Gavioli R, Tomatis R. Bioorg. Med. Chem. Lett. 2009; 19: 1966
• 26c Baldisserotto A, Destro F, Vertuani G, Marastoni M, Gavioli R, Tomatis R. Bioorg. Med. Chem. 2009; 17: 5535
• 26d Marastoni M, Baldisserotto A, Cellini S, Gavioli R, Tomatis R. J. Med. Chem. 2005; 48: 5038
• 26e Bang JK, Naka H, Teruya K, Aimoto S, Konno H, Nosaka K, Tatsumi T, Akaji K. J. Org. Chem. 2005; 70: 10596
• 27 Mellegaard-Waetzig SR, Wang C, Tunge JA. Tetrahedron 2006; 62: 7191