Organic Letters
Letter
(4) For selected examples of reductions with silanes, see:
(a) Jagadeesh, R. V.; Wienhofer, G.; Westerhaus, F. A.; Surkus, A.-
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E.; Pohl, M.-M.; Junge, H.; Junge, K.; Beller, M. Chem. Commun. 2011,
́
47, 10972. (b) Pehlivan, L.; Metay, E.; Laval, S.; Dayoub, W.;
Demonchaux, P.; Mignani, G.; Lemaire, M. Tetrahedron Lett. 2010, 51,
1939. (c) Rahaim, R. J.; Maleczka, R. E., Jr. Org. Lett. 2005, 7, 5087.
(5) For selected examples of reductions with metals other than iron,
see: (a) Matthews, J. M.; Greco, M. N.; Hecker, L. R.; Hoekstra, W. J.;
Andrade-Gordon, P.; de Garavilla, L.; Demarest, K. T.; Ericson, E.;
Gunnet, J. W.; Hageman, W.; Look, R.; Moore, J. B.; Maryanoff, B. E.
Bioorg. Med. Chem. Lett. 2003, 13, 753. (b) Gallagher, W. P.; Marlatt,
M.; Livingston, R.; Kiau, S.; Muslehiddinoglu, J. Org. Process Res. Dev.
2012, 16, 1665. (c) Lara, P.; Philippot, K. Catal. Sci. Technol. 2014, 4,
2445. (d) Jagadeesh, R. V.; Banerjee, D.; Arockiam, P. B.; Junge, H.;
Junge, K.; Pohl, M.-M.; Radnik, J.; Bruckner, A.; Beller, M. Green
̈
Chem. 2015, 17, 898.
(6) For representative examples of nitro reductions using Fe
nanoparticles, Fe/HCl, or Fe/NH4Cl, see: (a) Ramadas, K.;
Srinivasan, N. Synth. Commun. 1992, 22, 3189. (b) Liu, Y.; Lu, Y.;
Prashad, M.; Repic, O.; Blacklock, T. J. Adv. Synth. Catal. 2005, 347,
217. (c) Dey, R.; Mukherjee, N.; Ahammed, S.; Ranu, B. C. Chem.
Commun. 2012, 48, 7982. (d) Wang, L.; Li, P.; Wu, Z.; Yan, J.; Wang,
M.; Ding, Y. Synthesis 2003, 2001. (e) Desai, D. G.; Swami, S. S.;
Dabhade, S. K.; Ghagare, M. G. Synth. Commun. 2001, 31, 1249.
(f) Seixas, J. D.; Luengo-Arratta, S. A.; Diaz, R.; Saldivia, M.; Rojas-
Barros, D. I.; Manzano, P.; Gonzalez, S.; Berlanga, M.; Smith, T. K.;
Navarro, M.; Pollastri, M. P. J. Med. Chem. 2014, 57, 4834. (g) Wang,
S.; Li, Z.; Hua, W. Synth. Commun. 2002, 32, 3339.
827860 (accessed Nov 22, 2017).
(8) Quotations for a metric ton of CIP from three different suppliers
ranged from $5000 to $8000 as of April 2, 2017: Taian Health
Chemical Co., Ltd. ($5000); Chengdu Nuclear 857 New Chemicals
Co., Ltd. ($5900); Sichuan Kehui Industrial Co., Ltd. ($8000).
(9) Gabriel, C. M.; Lee, N. R.; Bigorne, F.; Klumphu, P.; Parmentier,
M.; Gallou, F.; Lipshutz, B. H. Org. Lett. 2017, 19, 194.
(10) Kelly, S. M.; Lipshutz, B. H. Org. Lett. 2014, 16, 98.
(11) Diederen, A. M. Metal Minerals Scarcity: A Call for Managed
Austerity and Elements of Hope; TNO Defence, Security and Safety:
Rijswijk, The Netherlands, 2009.
(12) (a) Feng, J.; Handa, S.; Gallou, F.; Lipshutz, B. H. Angew. Chem.,
Int. Ed. 2016, 55, 8979. (b) Gabriel, C. M.; Parmentier, M.; Riegert,
C.; Lanz, M.; Handa, S.; Lipshutz, B. H.; Gallou, F. Org. Process Res.
Dev. 2017, 21, 247.
(13) For another example of nitro group reductions using NPs/
NaBH , see: Goksu, H. New J. Chem. 2015, 39, 8498.
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(14) (a) Lipshutz, B. H.; Ghorai, S. Green Chem. 2014, 16, 3660.
(b) La Sorella, G.; Strukul, G.; Scarso, A. Green Chem. 2015, 17, 644.
(15) Isley, N. A.; Linstadt, R. T. H.; Kelly, S. M.; Gallou, F.; Lipshutz,
B. H. Org. Lett. 2015, 17, 4734.
(16) Sheldon, R. A. Chem. Ind. 1992, 903. Sheldon, R. A. Green
Chem. 2017, 19, 18.
(17) Lipshutz, B. H.; Isley, N. A.; Fennewald, J. C.; Slack, E. D.
Angew. Chem., Int. Ed. 2013, 52, 10952.
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