Please do not adjust margins
New Journal of Chemistry
Page 6 of 6
ARTICLE
Journal Name
17
18
MHz, CDCl3) δ 8.67 (d, J = 2.6 Hz, 1H), 7.92 (dd, J = 8.4, 4.0 Hz,
2H), 7.31‐7.28 (m, 1H), 7.18 (dd, J = 9.0, 2.6 Hz, 1H), 6.92 (d, J =
2.5 Hz, 1H), 3.97 (s, 2H).
DOI: 10.1039/C5NJ00917K
reduction at 100 oC. However, when we preformed the reaction at 83 oC,
only low yield (< 5%) of aniline was achieved.
1‐Methyl‐1H‐indol‐5‐amine (Table 2, entry 23).29 1‐Methyl‐
[IrCp*Cl2]2 as hydrogen transfer catalyst, see: T. Suzuki, Chem. Rev.
2011, 111, 1825-1845. b) A. C. Marr, Catal. Sci. Technol. 2012, 2, 279-
287.
5‐nitro‐1H‐indole
(88 mg, 0.5 mmol)was reacted following
the general procedure, and isolated by flash column
chromatography on silica gel (initially eluted with 1% Et3N in
PE) eluted by 20% EtOAc/PE, and then 100% EtOAc, yielding
the product as a brown solid (69 mg, 95%). GCMS (EI) m/z: 146
(M+); 1H NMR (500 MHz, CDCl3) δ 7.12 (d, J = 8.6 Hz, 1H), 6.94
(dd, J = 17.0, 2.5 Hz, 2H), 6.69 (dd, J = 8.6, 2.1 Hz, 1H), 6.29 (d, J
= 2.9 Hz, 1H), 3.71 (s, 3H), 3.48 (s, 2H).
19
20
A. Aranyos, G. Csjernyik, K. J. Szabó, J.-E. Bäckvall, Chem. Commun.
1999, 351-352.
In the first half hour, phenylhydroxylamine should exist in the reaction
system.
21
22
H. U. Blaser, Science 2006, 313, 312-313.
For base mediated reduction of nitrobenzenes leading to azobenzenes,
see: S. H. Gund, R. S. Shelkar, J. M. Nagarkar, RSC Adv., 2014, 4,
42947-42951.
23
24
25
26
27
D. A. Evans, H.-J. Song, K. R. Fandrick, Org. Lett., 2006, 8, 3351-3354.
S. M. Kelly, B. H. Lipshutz, Org. Lett. 2014, 16, 98-101.
P. L. Gkizis, M. Stratakis, I. N. Lykakis, Catal. Commun. 2013, 36, 48-51.
Sigma Aldrich, FTNMR (CAS: 626-43-7).
Notes and references
1
Lawrence, S. A. Amines: Synthesis Properties and Applications,
H. Wang, K. Wen, N. Nurahmat, Y. Shao, H. Zhang, C. Wei, Y. Li, Y.-J.
Shen, Z.-H. Sun, Beilstein J. Org. Chem. 2012, 8, 744-748.
Y. Wang, Q. Zhu, Adv. Synth. Catal. 2012, 354, 1902-1908.
V. Gasparotto, I. Castagliuolo, M. G. Ferlin, J. Med. Chem. 2007, 50,
5509-5513.
Cambridge University Press, Cambridge, 2004.
2
For the reduction of azides, see: a) S. Ahammed, A. Saha, B. C. Ranu, J.
Org. Chem. 2011, 76, 7235-7239. For the amination of aryl halides, see:
b) Y. Aubin, C. Fischmeister, C. M. Thomas, J. L. Renaud, Chem. Soc.
Rev. 2010, 39, 4130-4145.
28
29
3
a) R. S. Downing, P. J. Kunkeler, H. van Bekkum, Catal. Today 1997, 37,
121-136. b) Aromatic Nitro Compounds, H. U. Blaser, U. Siegrist, H.
Steiner, M. Studer, in Fine Chemicals through Heterogeneous Catalysis
(Eds.: R. A. Sheldon, H. van Bekkum), Wiley, New York, 2001, p. 389-
406. c) A. M. Tafesh, J. Weiguny, Chem. Rev. 1996, 96, 2035-2052. d) J.
P. Adams, J. Chem. Soc., Perkin Trans. 1, 2002, 2586-2597.
a) K. Junge, B. Wendt, N. Shaikh, M. Beller, Chem. Commun. 2010, 46,
1769-1771. b) S. Park, I. S. Lee, J. Park, Org. Biomol. Chem. 2013, 11,
395-399.
4
5
6
a) L.-Y. Li, Z.-L. Chen, H. Zhong, R.-H. Wang, Chem. Eur. J. 2014, 20,
3050-3060. b) A. J. MacNair, M. M. Tran, J. E. Nelson, G. U. Sloan, A.
Ironmonger, S. P. Thomas, Org. Biomol. Chem. 2014, 12, 5082-5088.
a) E. Vasilikogiannaki, C. Gryparis, V. Kotzabasaki, I. N. Lykakis, M.
Stratakis, Adv. Synth. Catal. 2013, 355, 907-911. b) H. Göksu, S. F. Ho,
Ö. Metin, K. Korkmaz, A. Mendoza Garcia, M. S. Gültekin, S. Sun, ACS
Catal. 2014, 4, 1777-1782.
7
a) S.-C. Wu, G.-D. Wen, X.-M. Liu, B.-W. Zhong, D.-S. Su,
ChemCatChem 2014, 6, 1558-1561. b) Z.-K. Zhao, H.-L. Yang, Y. Li, X.-
W. Guo, Green Chem. 2014, 16, 1274-1281.
8
9
P. F. Vogt, J. J. Gerulis, Ullmann’s Encyclopedia of Industrial Chemistry,
Wiley-VCH, Weinheim, Germany, 2000.
a) P. Rylander, In Catalytic Hydrogenation in Organic Synthesis;
Academic Press: New York, 1979, p 112. b) S. Nishimura, Handbook of
Heterogeneous Hydrogenation of Organic Synthesis, Wiley, New York,
2001; c) H.-U. Blaser, H. Steiner, M. Studer, ChemCatChem 2009, 1,
210-221.
10
11
X.-D. Wang, M.-H. Liang, J.-L. Zhang, Y. Wang, Curr. Org. Chem. 2007,
11, 299-314.
a) R. A. W. Johnstone, A. H. Wilby, I. D. Entwistle, Chem. Rev. 1985, 85,
129-170. b) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97-102.
c) J.-i. Ito, H. Nishiyama, Tetrahedron Lett. 2014, 55, 3133-3146.
a) G. Mestroni, G. Zassinovich, C. del Bianco and A. Camus, J. Mol.
Catal., 1983, 18, 33-40. b) C.-Y. Wang, C.-F. Fu, Y.-H. Liu, S.-M. Peng,
S.-T. Liu, Inorg. Chem. 2007, 46, 5779-5786. c) S. Hohloch, L. Suntrup, B.
Sarkar, Organometallics 2013, 32, 7376-7385.
12
13
14
15
X. Liu, S. Ye, H.-Q. Li, Y.-M. Liu, Y. Cao, K.-N. Fan, Catal. Sci. Technol.
2013, 3, 3200-3206.
R. V. Jagadeesh, G. Wienhofer, F. A. Westerhaus, A. E. Surkus, H.
Junge, K. Junge, M. Beller, Chem. Eur. J. 2011, 17, 14375-14379.
a) M. D. Le Page, B. R. James, Chem. Commun. 2000, 1647-1648. b) D.
Tavor, I. Gefen, C. Dlugy, A. Wolfson, Synthetic Commun. 2011, 41,
3409-3416.
16
S.-J. Chen, G.-P. Lu, C. Cai, Synthesis 2014, 46, 1717-1724.
6 | J. Name., 2012, 00, 1‐3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins