A Photo Touch on Amines: New Synthetic Adventures of Nitrogen Radical Cations

Abstract

Amines have been used as sacrificial electron donors to reduce photoexcited Ru(II) or Ir(III) complexes, during which they are oxidized to nitrogen radical cations. Recently, the synthetic potential of these nitrogen radical cations have caught synthetic organic chemists’ attention. They have been exploited in various transformations yielding a number of elegant methods for amine synthesis. This article highlights recent developments on nitrogen radical cation chemistry under visible-light photocatalysis.

Key words

amines - visible light - nitrogen radical cations - ruthenium - iridium

• References

• 1a Joule JA, Mills K. Heterocyclic Chemistry. Wiley; Chichester: 2010. 5th ed.
• 1b Mack, D. J.; Weinrich, M. L.; Vitaku, E.; Njarðarson, J. T. Top 200 Brand Name Drugs by US Retail Sales in 2010; http://cbc.arizona.edu/njardarson/group/top-pharmaceuticals-poster.
• 2 Constable DJ. C, Dunn PJ, Hayler JD, Humphrey GR, Leazer JL. Jr, Linderman RJ, Lorenz K, Manley J, Pearlman BA, Wells A, Zaks A, Zhang TY. Green. Chem. 2007; 9: 411
• 3a Inagaki A, Akita M. Coord. Chem. Rev. 2010; 254: 1220
• 3b Juris A, Balzani V, Barigelletti F, Campagna S, Belser P, Zelewsky AV. Coord. Chem. Rev. 1988; 84: 85
• 3c Kalyanasundaram K, Grätzel M. Coord. Chem. Rev. 1998; 177: 347
• 4a Lowry MS, Bernhard S. Chem.–Eur. J. 2006; 12: 7970
• 4b Flamigni L, Barbieri A, Sabatini C, Ventura B, Barigelletti F. Top. Curr. Chem. 2007; 281: 143
• 5a Sprintschnik G, Sprintschnik HW, Kirsch PP, Whitten DG. J. Am. Chem. Soc. 1976; 98: 2337
• 5b O’Regan B, Grätzel M. Nature (London) 1991; 353: 737

For recent reviews on photoredox catalysis, see:
• 6a Tucker JW, Stephenson CR. J. J. Org. Chem. 2012; 77: 1617
• 6b Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
• 6c Teplý F. Collect. Czech. Chem. Commun. 2011; 76: 859
• 6d Yoon TP, Ischay MA, Du J. Nat. Chem. 2010; 2: 527
• 6e Zeitler K. Angew. Chem. Int. Ed. 2009; 48: 9785
• 7a Nagib DA, MacMillan DW. C. Nature (London) 2011; 480: 224
• 7b Pham PV, Nagib DA, MacMillan DW. C. Angew. Chem. Int. Ed. 2011; 50: 6119
• 7c Nicewicz DA, MacMillan DW. C. Science 2008; 322: 77
• 8a Lin S, Ischay MA, Fry CG, Yoon TP. J. Am. Chem. Soc. 2011; 133: 19350
• 8b Lu Z, Shen M, Yoon TP. J. Am. Chem. Soc. 2011; 133: 1162
• 8c Ischay MA, Lu Z, Yoon TP. J. Am. Chem. Soc. 2010; 132: 8572
• 9a Wallentin C.-J, Nguyen JD, Finkbeiner P, Stephenson CR. J. J. Am. Chem. Soc. 2012; 134: 8875
• 9b Furst L, Narayanam JM. R, Stephenson CR. J. Angew. Chem. Int. Ed. 2011; 50: 9655
• 9c Dai C, Narayanam JM. R, Stephenson CR. J. Nat. Chem. 2011; 3: 140
• 9d Narayanam JM. R, Tucker JW, Stephenson CR. J. J. Am. Chem. Soc. 2009; 131: 8756
• 10a Koike T, Akita M. Chem. Lett. 2009; 38: 166
• 10b Yasu Y, Koike T, Akita M. Chem. Commun. 2012; 48: 5355
• 11a Zhu M, Zheng N. Synthesis 2011; 2223
• 11b Maity S, Zhu M, Shinabery RS, Zheng N. Angew. Chem. Int. Ed. 2012; 51: 222

Some recent examples of photocatalytic reactions:
• 12a Hari DP, Schroll P, König B. J. Am. Chem. Soc. 2012; 134: 2958
• 12b Zou Y.-Q, Chen J.-R, Liu X.-P, Lu L.-Q, Davis RL, Jørgensen KA, Xiao W.-J. Angew. Chem. Int. Ed. 2012; 51: 784
• 12c Kalyani D, McMurtrey KB, Neufeldt SR, Sanford MS. J. Am. Chem. Soc. 2011; 133: 18566
• 12d Larraufie M.-H, Pellet R, Fensterbank L, Goddard J.-P, Lacote E, Malacria M, Ollivier C. Angew. Chem. Int. Ed. 2011; 50: 4463
• 12e Neumann M, Fuldner S, König B, Zeitler K. Angew. Chem. Int. Ed. 2011; 50: 951
• 12f Andrews RS, Becker JJ, Gagné MR. Org. Lett. 2011; 13: 2406
• 12g Su Y, Zhang L, Jiao N. Org. Lett. 2011; 13: 2168
• 12h Zlotorzynska M, Sammis GM. Org. Lett. 2011; 13: 6264
• 12i Maji T, Karmakar A, Reiser O. J. Org. Chem. 2011; 76: 736
• 12j Chen Y, Kamlet AS, Steinman JB, Liu DR. Nat. Chem. 2011; 3: 146
• 12k Liu Q, Li Y.-N, Zhang H.-H, Chen B, Tung C.-H, Wu L.-Z. J. Org. Chem. 2011; 76: 1444
• 12l Zhou L, Yang H, Wang P. J. Org. Chem. 2011; 76: 5873
• 12m Andrews RS, Becker JJ, Gagné MR. Angew. Chem. Int. Ed. 2010; 49: 7274
• 12n Borak JB, Falvey DE. J. Org. Chem. 2009; 74: 3894
• 13 DeLaive PJ, Lee JT, Sprintschnik HW, Abruña H, Meyer TJ, Whitten DG. J. Am. Chem. Soc. 1977; 99: 7094

For utilization of α-amino alkyl radicals in organic reactions, see:
• 14a MacNally A, Prier CK, MacMillan DW. C. Science 2011; 334: 1114
• 14b Miyake Y, Nakajima K, Nishibayashi Y. J. Am. Chem. Soc. 2012; 134: 3338
• 14c Kohls P, Jadhav D, Pandey G, Reiser O. Org. Lett. 2012; 14: 672

For utilization of iminium ions in organic reactions, see:
• 15a Freeman DB, Furst L, Condie AG, Stephenson CR. J. Org. Lett. 2012; 14: 94
• 15b Condie AG, González-Gómez JC, Stephenson CR. J. J. Am. Chem. Soc. 2010; 132: 1464
• 15c Rueping M, Leonori D, Poisson T. Chem. Commun. 2011; 47: 9615
• 15d DiRocco DA, Rovis T. J. Am. Chem. Soc. 2012; 134: 8094
• 15e Hari DP, König B. Org. Lett. 2011; 13: 3852
• 15f Pan Y, Wang S, Kee CW, Dubuisson E, Yang Y, Loh KP, Tan C.-H. Green. Chem. 2011; 13: 3341
• 15g Wang C, Xie Z, deKrafft KE, Lin W. J. Am. Chem. Soc. 2011; 133: 13445
• 15h Pirtsch M, Paria S, Matsuno T, Isobe H, Reiser O. Chem.–Eur. J. 2012; 18: 7336
• 15i Rueping M, Zhu S, Koenigs RM. Chem. Commun. 2011; 47: 12709
• 15j Zou Y.-Q, Lu L.-Q, Fu L, Chang N.-J, Rong J, Chen J.-R, Xiao W.-J. Angew. Chem. Int. Ed. 2011; 50: 7171
• 16 Zhu, M.; Durham, B.; Zheng, N. unpublished results.
• 17 Crutchley RJ, Lever AB. P. J. Am. Chem. Soc. 1980; 102: 7129
• 18 Shinabery, R. S.; Zheng, N. unpublished results.
• 19 Wimalasena K, Wickman HB, Mahindaratne MP. D. Eur. J. Org. Chem. 2001; 3811
• 20a Madelaine C, Six Y, Buriez O. Angew. Chem. Int. Ed. 2007; 46: 8046
• 20b Lee HB, Sung MJ, Blackstock SC, Cha JK. J. Am. Chem. Soc. 2001; 123: 11322
• 20c Takemoto Y, Yamagata S, Furuse S, Hayase H, Echigo T, Iwata C. Chem. Commun. 1998; 651
• 20d Lee J, U, J. S.; Blackstock SC, Cha JK. J. Am. Chem. Soc. 1997; 119: 10241
• 20e Larquetoux L, Kowalska JA, Six Y. Eur. J. Org. Chem. 2004; 3517
• 20f Larquetoux L, Ouhamou N, Chiaroni A, Six Y. Eur. J. Org. Chem. 2005; 4654
• 20g Lee J, Berritt S, Prier CK, Joullié MM. Org. Lett. 2011; 13: 1083