Atom-Economical C₂ + N₁ Aziridination: Progress towards Catalytic Intermolecular Reactions Using Alkenes and Aryl Azides

Abstract

The direct synthesis of aziridines from alkenes and a nitrene source with the correct functionality on the nitrogen atom has remained an elusive goal in synthetic chemistry. Ruthenium, cobalt, and iron porphyrin complexes have been demonstrated to catalyze the formation of aziridines from electron-withdrawing aryl azides and a limited selection of conjugated alkenes. Our group is expanding the scope of catalytic aziridination to include electron-donating aryl azides and aliphatic alkenes through the use of a novel tetracarbene iron catalyst.

Key words

azides - alkenes - catalysis - aziridination - transition metals

• References

• 1a Aziridines and Epoxides in Organic Synthesis. Yudin AK. Wiley-VCH; Weinheim: 2006
• 1b Singh GS, D’hooghe M, De Kimpe N. Chem. Rev. 2007; 107: 2080
• 2a Kasai M, Kono M. Synlett 1992; 778
• 2b Hartley JA, Hazrati A, Kelland LR, Khanim R, Shipman M, Suzenet F, Walker LF. Angew. Chem. Int. Ed. 2000; 39: 3467
• 2c Coleman RS, Perez RJ, Burk CH, Navarro A. J. Am. Chem. Soc. 2002; 124: 13008
• 2d Colandrea VJ, Rajaraman S, Jimenez LS. Org. Lett. 2003; 5: 785
• 3a Lu P. Tetrahedron 2010; 66: 2549
• 3b Schneider C. Angew. Chem. Int. Ed. 2009; 48: 2082
• 3c Hu XE. Tetrahedron 2004; 60: 2701
• 4a Krake SH, Bergmeier SC. Tetrahedron 2010; 66: 7337
• 4b Dauban P, Malik G. Angew. Chem. Int. Ed. 2009; 48: 9026
• 5 Somfai P, Panknin O. Synlett 2007; 1190
• 6a Karila D, Dodd RH. Curr. Org. Chem. 2011; 15: 1507
• 6b Chang JW. W, Ton TM. U, Chan PW. H. Chem. Rec. 2011; 11: 331
• 7 Mansuy D, Mahy JP, Dureault A, Bedi G, Battioni P. J. Chem. Soc., Chem. Commun. 1984; 1161
• 8a Pellissier H. Tetrahedron 2010; 66: 1509
• 8b Mueller P, Fruit C. Chem. Rev. 2003; 103: 2905
• 9a Sodergren MJ, Alonso DA, Bedekar AV, Andersson PG. Tetrahedron Lett. 1997; 38: 6897
• 9b Dauban P, Saniere L, Tarrade A, Dodd RH. J. Am. Chem. Soc. 2001; 123: 7707
• 10 Minakata S. Acc. Chem. Res. 2009; 42: 1172
• 11 Driver TG. Org. Biomol. Chem. 2010; 8: 3831
• 12a Katsuki T. Chem. Lett. 2005; 34: 1304
• 12b Kawabata H, Omura K, Uchida T, Katsuki T. Chem. Asian J. 2007; 2: 248
• 13a Dauban P, Dodd RH. J. Org. Chem. 1999; 64: 5304
• 13b Jones JE, Ruppel JV, Gao G.-Y, Moore TM, Zhang XP. J. Org. Chem. 2008; 73: 7260
• 13c Gao G, Jones JE, Vyas R, Harden JD, Zhang XP. J. Org. Chem. 2006; 71: 6655
• 14 Fantauzzi S, Caselli A, Gallo E. Dalton Trans. 2009; 5434
• 15a Li Y, Gao L, Han F. Chem.–Eur. J. 2010; 16: 7969
• 15b Tao C, Cui X, Li J, Liu A, Liu L, Guo Q. Tetrahedron Lett. 2007; 48: 3525
• 15c Andersen J, Madsen U, Bjorkling F, Liang X. Synlett 2005; 2209
• 15d Zhu W, Ma D. Chem. Commun. 2004; 888
• 15e Smith PA. S, Brown BB. J. Am. Chem. Soc. 1951; 73: 2438
• 16 Cenini S, Tollari S, Penoni A, Cereda C. J. Mol. Catal. A: Chem. 1999; 137: 135
• 17a Fantauzzi S, Gallo E, Caselli A, Ragaini F, Macchi P, Casati N, Cenini S. Organometallics 2005; 24: 4710
• 17b Fantauzzi S, Gallo E, Caselli A, Piangiolino C, Ragaini F, Cenini S. Eur. J. Org. Chem. 2007; 6053
• 18a Piangiolino C, Gallo E, Caselli A, Fantauzzi S, Ragaini F, Cenini S. Eur. J. Org. Chem. 2007; 743
• 18b Fantauzzi S, Gallo E, Caselli A, Piangiolino C, Ragaini F, Re N, Cenini S. Chem.–Eur. J. 2009; 15: 1241
• 19 Caselli A, Gallo E, Fantauzzi S, Morlacchi S, Ragaini F, Cenini S. Eur. J. Inorg. Chem. 2008; 3009
• 20 Liu Y, Che C. Chem.–Eur. J. 2010; 16: 10494
• 21 Bass HM, Cramer SA, Price JL, Jenkins DM. Organometallics 2010; 29: 3235
• 22a Kyba EP, Hudson CW, McPhaul MJ, John AM. J. Am. Chem. Soc. 1977; 99: 8053
• 22b Kyba EP, Davis RE, Hudson CW, John AM, Brown SB, McPhaul MJ, Liu L, Glover AC. J. Am. Chem. Soc. 1981; 103: 3868
• 23a McKie R, Murphy JA, Park SR, Spicer MD, Zhou S. Angew. Chem. Int. Ed. 2007; 46: 6525
• 23b Park SR, Findlay NJ, Garnier J, Zhou S, Spicer MD, Murphy JA. Tetrahedron 2009; 65: 10756
• 23c Findlay NJ, Park SR, Schoenebeck F, Cahard E, Zhou S, Berlouis LE. A, Spicer MD, Tuttle T, Murphy JA. J. Am. Chem. Soc. 2010; 132: 15462
• 24 Cramer SA, Jenkins DM. J. Am. Chem. Soc. 2011; 133: 19342
• 25a Thomas CM, Mankad NP, Peters JC. J. Am. Chem. Soc. 2006; 128: 4956
• 25b Nieto I, Ding F, Bontchev RP, Wang H, Smith JM. J. Am. Chem. Soc. 2008; 130: 2716
• 26 Bolm C, Legros J, LePaih J, Zani L. Chem. Rev. 2004; 104: 6217
• 27 For a example of aziridination with alkyl azides, see: King ER, Hennessy ET, Betley TA. J. Am. Chem. Soc. 2011; 133: 4917