10.1002/chem.201803347
Chemistry - A European Journal
COMMUNICATION
[4]
[5]
D. C. Nonhebel, W. A. Waters, Proc R Soc Lond A Math Phys Sci.
1957, 242, 16–27.
which has a broad substrate scope is attractive as it installs
iodine, bromine and chlorine, is independent of the substitution
present on the arylamines and is scalable. The use of NaNO2
and BF3.Et2O in DMF for efficient hydrodeamination of arylamine
was also demonstrated.
(a) G. Balz, G. Schiemann, Ber. Dtsch. Chem. Ges. 1927, 60, 1186–
1890; (b) C. G. Swain, R. J. Rogers, J. Am. Chem. Soc. 1975, 97, 799–
800; (c) K. K. Laali, V. J. Gettwert, J. Fluorine Chem. 2001, 107, 31–34.
(a) J. I. G. Cadogan, D. A. Roy, D. M. Smith, J. Chem. Soc. C 1966,
1249–1250; (b) F. Mo, D. Qiu, Y. Zhang, J. Wang, Acc. Chem. Res.
2018, 51, 496−506.
[6]
[7]
(a) S. Wang, D. Qiu, F. Mo, Y. Zhang, J. Wang, J. Org. Chem., 2016,
81, 11603–11611; (b) L. He, G. Qiu, Y. Gao, J. Wu, Org. Biomol. Chem.
2014, 12, 6965−6971 and references therein. (c) C.-J. Zhao, D. Xue,
Z.-H. Jia, C. Wang, J. Xiao, Synlett, 2014, 25, 1577–1584; (d) X. Yang,
L. Shi, H. Fu, Synlett 2014, 25, 847–852; (e) N. Susperregui, K. Miqueu,
J.-M. Sotiropoulos, F. L. Callonnec, E. Fouquet, F.-X. Felpin, Chem.
Eur. J. 2012, 18, 7210–7218.
Experimental Section
Full experimental and characterization details for all compounds are
included in supporting information.
Acknowledgements
[8]
[9]
(a) S. H. Korzeniowski, L. Blum, G. W. Gokel, Tetrahedron Lett. 1977,
18, 1871–1874; (b) R. A. Bartsch, I. W. Yang, Tetrahedron Lett. 1979,
20, 2503–2504.
SM acknowledges CSIR, New Delhi for the financial assistance
in the form of fellowship. Authors acknowledge SAIF Division of
CDRI for providing the spectroscopic data. This work was
funded by the CSIR Network project BSC-0114.
H. J. Lucas, E. R. Kennedy, Org. Synth. 1943, 2, 351.
[10] (a) M. P. Doyle, B. Siegfried, J. F. Jr. Dellaria, J. Org. Chem. 1977, 42,
2426−2431; (b) H. H. Hodgson, J. Walker, J. Chem. Soc. 1933,
1620−1621; (c) M. A. Karimi Zarchi, S. Z. Mousavi, J. Polym. Res. 2014,
21, 1−9; (d) H. Ku, J. R. Barrio, J. Org. Chem. 1981, 46, 5239−5241.
[11] D. A. Leas, Y. Dong, J. L. Vennerstrom, D. E. Stack, Org. Lett. 2017, 19,
2518–2521.
Keywords: Amines • Sodium nitrite • N-halosuccinimide •
Halogenation • hydrodeamination
[12] (a) S. U. Dighe, S. Mukhopadhyay, S. Kolle, S. Kanojiya, S. Batra,
Angew. Chem. Int. Ed. 2015, 54, 10926–10930; (b) S. Mukhopadhyay,
S. U. Dighe, S. Kolle, P. K. Shukla, S. Batra, Eur. J. Org. Chem. 2016,
3836–3844; (c) S. U. Dighe, S. Mukhopadhyay, K. Priyanka, S. Batra,
Org. Lett. 2016, 18, 4190–4193.
[1]
(a) A. Biffis, P. Centomo, A. Del Zotto, M. Zecca, Chem. Rev. 2018,
118, 2249−2295; (b) S. Bhunia, G. G. Pawar, S. V. Kumar, Y. Jiang, D.
Ma, Angew. Chem. Int. Ed. 2017, 56, 16136−16179; Angew. Chem.
2017, 129, 16352-16397; (c) J. P. G. Rygus, C. M. Crudden, J. Am.
Chem. Soc. 2017, 139, 18124−18137; (d) P. Nareddy, F. Jordan, M.
Szostak, ACS Catal. 2017, 7, 5721−5745; (e) H. Zeng, Z. Qiu, A.
Dominguez-Huerta, Z. Hearne, Z. Chen, C.-J. Li, ACS Catal. 2017, 7,
510−519; (f) J. Almond-Thynne, D. C. Blakemore, D. C. Pryde, A. C.
Spivey, Chem. Sci. 2017, 8, 40−62; (g) F. Bellina, Top. Organomet.
Chem. 2016, 55, 77−102; (h) P. Ruiz-Castillo, S. L. Buchwald, Chem.
Rev. 2016, 116, 12564−12649; (i) O. M. Kuzmina, A. K. Steib, A.
Moyeux, G. Cahiez, P. Knochel, Synthesis 2015, 47, 1696−1705; (j) K.
C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem., Int. Ed. 2005, 44,
4442−4489, Angew. Chem. 2005, 117, 4516-4563.
[13] J. G. Lee, H. T. Cha, Tetrahedron Lett. 1992, 33, 3167–3168.
[14] (a) F. Csende, Mini-Rev.Org. Chem. 2015, 12, 127–148; (b) Y. Yan, H.
Li, B. Niua, C. Zhua, T. Chen, Y. Liu, Tetrahedron Lett. 2016, 57, 4170–
4173.
[15] M. Nakajima, J. C. Warner, J. -P. Anselme, Tetrahedron Lett. 1984, 25,
2619–2622.
[16] H. Suzuki, N. Nonoyama, Tetrahedron Lett. 1998, 39, 4533–4536.
[17] M. Miyahara, S. Kamiya, M. Nakadate, Chem. Pharm. Bull. 1983, 30,
41–44.
[18] J. G. Lee, K. H. Kwak, J. P. Hwang, Tetrahedron Lett. 1990, 31, 6677–
6680.
[2]
[3]
(a) M. T. Cabrita, C. Vale, A. P. Rauter, Mar. Drugs 2010, 8,
2301−2317; (b) Y. Li, B. Guo, Z. Xu, B. Li, T. Cai, X. Zhang, Y. Yu, H.
Wang, J. Shi, W. Zhu, Sci. Rep. 2016, 6, 31074; (c) R. Wilcken, M. O.
Zimmermann, A. Lange, A. C. Joerger, F. M. Boeckler, J. Med. Chem.
2013, 56, 1363−1388; (d) Y. Lu, Y. Liu, Z. Xu, H. Li, H. Liu, W. Zhu,
Expert Opin. Drug Discovery 2012, 7, 375−383; (e) Z. Xu, Z. Yang, Y.
Liu, Y. Lu, K. Chen, W. Zhu, J. Chem. Inf. Model. 2014, 54, 69−78.
(a) T. Sandmeyer, Ber. Dtsch. Chem. Ges. 1884, 17, 1633−1635; (b) T.
Sandmeyer, Ber. Dtsch. Chem. Ges. 1884, 17, 2650−2653; (c) H. H.
Hodgson, Chem. Rev. 1947, 40, 251–277 and references cited therein.
(d) W. A. Cowdrey, D. S. Davies, Q. Rev. Chem. Soc. 1952, 6, 358–
379; (e) H. Zoliinger, “Azo and Diazo Chemistty", Interscience. New
York, 1961; (f) P. A. S. Smith, The Chemistry of Open Chain Organic
Nitrogen compounds, Vol. 2, W. A. Benjamin, New York, 1966.
[19] M. P. Doyle, J. F. Jr. Dellaria, B. Siegfried, S. W. Bishop, J. Org. Chem.
1977, 42, 3494–3498.
[20] The reaction of t-BuONO and BF3.Et2O in dichloromethane leads to
formation of nitrosyl fluoride (NOF); M. P. Doyle, W. J. Bryker, J. Org.
Chem. 1978, 44, 1572–574.
[21] B. Xing, C. Ni, J. Hu, Angew. Chem. Int. Ed. 2018, 7, 9896–9900.
Angew. Chem. 2018, 130, 10044–10048.
[22] A few citations only- (a) D. Felipe-Blanco, F. Alonso, J. C. Gonzalez-
Gomez, Adv. Synth. Catal. 2017, 359, 2857 – 2863; (b) K. Burglova, S.
Okorochenkov, Jan Hlavac, Org. Lett. 2016, 18, 3342−3345; (c) M.
Majek, F. Filace, A. J. von Wangelin, Chem. Eur. J. 2015, 21, 4518 –
4522; (d) Y. Wang, F. S. Guziec Jr., J. Org. Chem. 2001, 66, 8293-
8296. (e) O. J. Geoffroy, T. A. Morinelli, G. P. Meier, Tetrahedron Lett.
2016, 42, 5367-5369.
This article is protected by copyright. All rights reserved.