10.1002/chem.202102354
Chemistry - A European Journal
COMMUNICATION
[10] For selected reviews, see: a) J.-T. Yu, F. Teng, J. Cheng, Adv. Synth.
Catal. 2017, 359, 26-38; b) M.-H. Larraufie, G. Maestri, M. Malacria, C.
Ollivier, L. Fensterbank, E. Lacôte, Synthesis 2012, 44, 1279-1292.
[11] C. Zhu, J.-B. Xia, C. Chen, Org. Lett. 2014, 16, 247-249.
[12] N. Kuhl, S. Raval, R. D. Cohen, Org. Lett. 2019, 21, 1268-1272.
[13] a) J. N. Ayres, M. W. Ashford, Y. Stöckl, V. Prudhomme, K. B. Ling, J. A.
Platts, L. C. Morrill, Org. Lett. 2017, 19, 3835-3838; b) J. N. Ayres, M. T.
J. Williams, G. J. Tizzard, S. J. Coles, K. B. Ling, L. C. Morrill, Org. Lett.
2018, 20, 5282-5285.
We are grateful to The Fundamental Research Funds for the
Central Universities (HUST), Guangdong Basic and Applied Basic
Research Foundation (2019A1515110788), and Hubei
Technological Innovation Project (2019ACA125) for financial
support. We also thank the Analytical and Testing Centre of HUST,
Analytical and Testing Centre of the school of Chemistry and
Chemical Engineering (HUST) for data characterizing.
[14] J. N. Ayres, K. B. Ling, L. C. Morrill, Org. Lett. 2016, 18, 5528-5531.
[15] a) S. A. Bakunov, A. V. Rukavishnikov, A. V. Tkachev, Synthesis 2000,
2000, 1148-1159; b) C.-C. Lin, T.-H. Hsieh, P.-Y. Liao, Z.-Y. Liao, C.-W.
Chang, Y.-C. Shih, W.-H. Yeh, T.-C. Chien, Org. Lett. 2014, 16, 892-895;
c) G. Zhang, Y. Zhao, C. Ding, Org. Biomol. Chem. 2019, 17, 7684-7688;
d) E. Duchamp, S. Hanessian, Org. Lett. 2020, 22, 8487-8491; e) T.
Ramana, P. Saha, M. Das, T. Punniyamurthy, Org. Lett. 2010, 12, 84-87.
[16] F. Teng, J.-T. Yu, Y. Jiang, H. Yang, J. Cheng, Chem. Commun. 2014,
50, 8412-8415.
Keywords:
N-cyanation,
Amines,
Cyanamides,
Cyanobenziodoxolone, Electrophilic cyanation.
[1]
[2]
S. Matsunaga, H. Kobayashi, R. W. M. van Soest, N. Fusetani, J. Org.
Chem. 2005, 70, 1893-1896.
a) D. Lainé, M. Palovich, B. McCleland, E. Petitjean, I. Delhom, H. Xie,
J. Deng, G. Lin, R. Davis, A. Jolit, N. Nevins, B. Zhao, J. Villa, J. Schneck,
P. McDevitt, R. Midgett, C. Kmett, S. Umbrecht, B. Peck, A. B. Davis, D.
Bettoun, ACS Med. Chem. Lett. 2011, 2, 142-147; b) P. L. Feldman, M.
F. Brackeen, D. J. Cowan, B. E. Marron, F. J. Schoenen, J. A. Stafford,
E. M. Suh, P. L. Domanico, D. Rose, M. A. Leesnitzer, E. Sloan Brawley,
A. B. Strickland, M. W. Vergese, K. M. Connolly, R. Bateman-Fite, L.
Staton Noel, L. Sekut, S. A. Stimpson, J. Med. Chem. 1995, 38, 1505-
1510.
[17] a) K. Škoch, I. Cíarová, P. Štěpnicka, Chem. Eur. J. 2018, 24, 13788-
13791; b) S. Kamijo, T. Jin, Y. Yamamoto, J. Am. Chem. Soc. 2001, 123,
9453-9454; c) S. Kamijo, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124,
11940-11945.
[18] a) T. V. Hughes, S. D. Hammond, M. P. Cava, J. Org. Chem. 1998, 63,
401-402; b) P. Anbarasan, H. Neumann, M. Beller, Chem. Eur. J. 2011,
17, 4217-4222; c) J.-J. Kim, D.-H. Kweon, S.-D. Cho, H.-K. Kim, E.-Y.
Jung, S.-G. Lee, J. R. Falck, Y.-J. Yoon, Tetrahedron 2005, 61, 5889-
5894.
[3]
[4]
Y. Zhu, M. R. Loso, G. B. Watson, T. C. Sparks, R. B. Rogers, J. Z.
Huang, B. C. Gerwick, J. M. Babcock, D. Kelley, V. B. Hegde, B. M.
Nugent, J. M. Renga, I. Denholm, K. Gorman, G. J. DeBoer, J. Hasler, T.
Meade, J. D. Thomas, J. Agric. FoodChem. 2011, 59, 2950-2957.
a) D. D. Nekrasov, Russ. J. Org. Chem. 2004, 40, 1387-1402; b) J.
Sävmarker, J. Rydfjord, J. Gising, R. Odell, M. Larhed, Org. Lett. 2012,
14, 2394-2397; c) V. B. Panduranga, V. V. Sureshbabu, Tetrahedron Lett.
2013, 54, 975-979; d) M.-H. Larraufie, C. Ollivier, L. Fensterbank, M.
Malacria, E. Lacôte, Angew. Chem. Int. Ed. 2010, 49, 2178-2181; Angew.
Chem. 2010, 122, 2224-2227; e) C. Wang, D. Wang, F. Xu, B. Pan, B.
Wan, J. Org. Chem. 2013, 78, 3065-3072; f) R. L. Giles, J. D. Sullivan,
A. M. Steiner, R. E. Looper, Angew. Chem. Int. Ed. 2009, 48, 3116-3120;
Angew. Chem. 2009, 121, 3162-3166; g) G. Maestri, M.-H. Larraufie, C.
Ollivier, M. Malacria, L. Fensterbank, E. Lacôte, Org. Lett. 2012, 14,
5538-5541; h) T. K. Lane, B. R. D’Souza, J. Louie, J. Org. Chem. 2012,
77, 7555-7563; i) M.-H. Larraufie, C. Courillon, C. Ollivier, E. Lacôte, M.
Malacria, L. Fensterbank, J. Am. Chem. Soc. 2010, 132, 4381-4387.
a) F. Carta, A. Akdemir, A. Scozzafava, E. Masini, C. T. Supuran, J. Med.
Chem. 2013, 56, 4691-4700; b) R. Kumar, D. Rai, S. K. Sharma, H. A.
Saffran, R. Blush, D. L. J. Tyrrell, J. Med. Chem. 2001, 44, 3531-3538;
c) D. Guay, C. Beaulieu, M. D. Percival, Curr. Top. Med. Chem. 2010,
10, 708-716; d) D. N. Deaton, A. M. Hassell, R. B. McFayden, A. B. Miller,
L. R. Miller, L. M. Shewchuk, F. X. Tavares, D. H. Willard, L. L. Wright,
Bioorg. Med. Chem. Lett. 2005, 15, 1815-1819.
[19] a) X. Li, C. Golz, M. Alcarazo, Angew. Chem. Int. Ed. 2019, 58, 9496-
9500; Angew. Chem. 2019, 131, 9596-9600; b) G. Talavera, J. Peña, M.
Alcarazo, J. Am. Chem. Soc. 2015, 137, 8704-8707.
[20] a) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523-2584. b) A.
Yoshimura, V. V. Zhdankin, Chem. Rev. 2016, 116, 3328-3435. c) J. P.
Brand, J. Waser, Chem. Soc. Rev. 2012, 41, 4165-4179. d) X. Wang, A.
Studer, Acc. Chem. Res. 2017, 50, 1712-1714. e) J. Charpentier, N. Früh,
A. Togni, Chem. Rev. 2015, 115, 650-682.
[21] V. V. Zhdankin, C. J. Kuehl, A. P. Krasutsky, J. T. Bolz, B. Mismash, J.
K. Woodward, A. J. Simonsen, Tetrahedron Lett. 1995, 36, 7975-7978.
[22] a) F. Le Vaillant, M. D. Wodrich, J. Waser, Chem. Sci. 2017, 8, 1790-
1800; b) R. Chowdhury, J. Schörgenhumer, J. Novacek, M. Waser,
Tetrahedron Lett. 2015, 56, 1911-1914; c) X. Wang, A. Studer, Angew.
Chem. Int. Ed. 2018, 57, 11792-11796; Angew. Chem. 2018, 130,
11966-11970; d) B. Ma, X. Lin, L. Lin, X. Feng, X. Liu, J. Org. Chem.
2017, 82, 701-708; e) Y.-F. Wang, J. Qiu, D. Kong, Y. Gao, F. Lu, P. G.
Karmaker, F.-X. Chen, Org. Biomol. Chem. 2015, 13, 365-368; f) M.
Chen, Z.-T. Huang, Q.-Y. Zheng, Org. Biomol. Chem. 2015, 13, 8812-
8816.
[5]
[23] a) R. Frei, T. Courant, M. D. Wodrich, J. Waser, Chem. Eur. J. 2015, 21,
2662-2668; b) N. De-clas, F. Le Vaillant, J. Waser, Org. Lett. 2019, 21,
524-528.
[6]
[7]
a) R. J. Crutchley, Coord. Chem. Rev. 2001, 219-221, 125-155; b) J.
Xiang, W.-L. Man, S.-M. Yiu, S.-M. Peng, T.-C. Lau, Chem. Eur. J. 2011,
17, 13044-13051; c) H. S. Soo, J.-S. Figueroa, C. C. Cummins, J. Am.
Chem. Soc. 2004, 126, 11370-11376.
[24] For non-toxic cyanating agents involved cyanation reactions, see: A. M.
Nauth, T. Opatz, Org. Biomol. Chem. 2019, 17, 11-23. Caution! Although
CBX reagent is much easier to handle and less toxic than BrCN e.g., yet
CBX is a high-energy compound, and its preparation requires the use of
toxic TMSCN and it can release slowly cyanides in the presence of water,
thus, great care should be still taken when handling this reagent.
[25] Z. Chen, S. Zheng, Z. Wang, Z. Liao, W. Yuan, ChemPhotoChem 2021,
doi.org/10.1002/cptc.202100133.
a) Y.-q. Wu, D. C. Limburg, D. E. Wilkinson, G. S. Hamilton, Org. Lett.
2000, 2, 795-797; b) P. Anbarasan, H. Neumann, M. Beller, Angew.
Chem. Int. Ed. 2011, 50, 519-522; Angew. Chem. 2011, 123, 539-542;
c) T.-J. Gong, B. Xiao, W.-M. Cheng, W. Su, J. Xu, Z.-J. Liu, L. Liu, Y.
Fu, J. Am. Chem. Soc. 2013, 135, 10630-10633; d) M. Chaitanya, D.
Yadagiri, P. Anbarasan, Org. Lett. 2013, 15, 4960-4963.
[26] R. L. Giles, R. A. Nkansah, R. E. Looper, J. Org. Chem. 2010, 75, 261-
264.
[8]
[9]
a) O. Wallach, Ber. Dtsch. Chem. Ges. 1899, 32, 1872-1875; b) J. von
Braun, Ber. Dtsch. Chem. Ges. 1900, 33, 1438-1452; c) A. F. Cockerill,
A. Deacon, R. G. Harrison, D. J. Osborne, D. M. Prime, W. J. Ross, A.
Todd, J. P. Verge, Synthesis 1976, 1976, 591-593; d) T. Morgan, N. C.
Ray, D. M. Parry, Org. Lett. 2002, 4, 597-598.
a) W. E. Luttrell, J. Chem. Health. Saf. 2009, 16, 29-30; b) U.S. National
Library of Medicine, National Institutes of Health, Hazardous Substances
Data
Bank
(HSDB):
CNO+708 (accessed Jan 21, 2019) and references therein.
5
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