Communication
ChemComm
7 (a) D. B. Kimball and M. M. Haley, Angew. Chem., Int. Ed., 2002,
In summary, we have shown the first transformation of
triazenes into sulfonamides catalyzed by boron trifluoride
etherate or copper chloride. One of the advantages of our
procedure is the use of sulfur dioxide as the sulfonyl source.
We also found that the triazenes were more stable than the
equivalent diazonium salts, they could produce aryl amino
radicals under our conditions, and the utilization of these
two types of radicals may be valuable for other C–C and C–N
bond formation reactions.
¨
¨
41, 3338; (b) D. K. Kolmel, N. Jung and S. Brase, Aust. J. Chem., 2014,
67, 328.
8 T. B. Patrick, R. P. Willaredt and D. J. DeGonia, J. Org. Chem., 1985,
50, 2232.
9 (a) C. Galli, Chem. Rev., 1988, 88, 765; (b) H. Bonin, E. Fouquet and
F.-X. Felpin, Adv. Synth. Catal., 2011, 353, 3063; (c) F. Mo, G. Dong,
Y. Zhang and J. Wang, Org. Biomol. Chem., 2013, 11, 1582.
10 (a) H. Ku and J. R. Barrio, J. Org. Chem., 1981, 46, 5239;
(b) N. Satyamurthy, J. R. Barrio, D. G. Schmidt, C. Kammerer,
G. T. Bida and M. E. Phelps, J. Org. Chem., 1990, 55, 4560;
(c) T. Saeki, E.-C. Son and K. Tamao, Org. Lett., 2004, 6, 617;
(d) C.-Y. Liu, A. Gavryushin and P. Knochel, Chem. – Asian J., 2007,
2, 1020; (e) C. Zhu and M. Yamane, Org. Lett., 2012, 14, 4560.
11 A. S. Deeming, C. J. Russell, A. J. Hennessy and M. C. Willis, Org.
Lett., 2014, 16, 150.
The authors thank the State of Mecklenburg-Vorpommern,
the Bundesministerium fu¨r Bildung und Forschung (BMBF) and
the Deutsche Forschungsgemeinschaft for financial support.
12 F. R. Bichowsky, J. Am. Chem. Soc., 1922, 44, 116.
13 (a) B. Nguyen, E. J. Emmett and M. C. Willis, J. Am. Chem. Soc., 2010,
132, 16372; (b) E. J. Emmett, C. S. Richards-Taylor, B. Nguyen,
A. Garcia-Rubia, B. R. Hayter and M. C. Willis, Org. Biomol. Chem.,
2012, 10, 4007; (c) S. Ye and J. Wu, Chem. Commun., 2012, 48, 10037;
(d) S. Ye and J. Wu, Chem. Commun., 2012, 48, 7753;
(e) C. S. Richards-Taylor, D. C. Blakemore and M. C. Willis, Chem.
Sci., 2014, 5, 222.
14 S. T. Purrington and P. Wilder Jr, J. Org. Chem., 1965, 30, 2070.
15 (a) A. E. Hill, J. Am. Chem. Soc., 1931, 53, 2598; (b) A. E. Hill and
T. B. Fitzgerald, J. Am. Chem. Soc., 1935, 57, 250; (c) N. F. Albertson and
W. C. Fernelius, J. Am. Chem. Soc., 1943, 65, 1687; (d) J. M. Kanamueller,
J. Inorg. Nucl. Chem., 1971, 33, 4051; (e) P. S. Santos and R. Lieder, J. Mol.
Notes and references
1 (a) C. T. Supuran, A. Casini and A. Scozzafava, Med. Res. Rev., 2003,
23, 535; (b) C. T. Supuran, A. Innocenti, A. Mastrolorenzo and
A. Scozzafava, Mini-Rev. Med. Chem., 2004, 4, 189; (c) J. E. Lesch, The
First Miracle Drugs: How the Sulfa Drugs Transformed Medicine, Oxford
University Press, 2007; (d) J. D. Wilden, J. Chem. Res., 2010, 34, 541.
2 (a) L. De Luca and G. Giacomelli, J. Org. Chem., 2008, 73, 3967;
(b) K. Bahrami, M. M. Khodaei and M. Soheilizad, J. Org. Chem.,
2009, 74, 9287; (c) H. Veisi, R. Ghorbani-Vaghei, S. Hemmati and
J. Mahmoodi, Synlett, 2011, 2315; (d) A. Gioiello, E. Rosatelli,
M. Teofrasti, P. Filipponi and R. Pellicciari, ACS Comb. Sci., 2013,
15, 235; (e) A. V. Bogolubsky, Y. S. Moroz, P. K. Mykhailiuk,
S. E. Pipko, A. I. Konovets, I. V. Sadkova and A. Tolmachev, ACS
Comb. Sci., 2014, 16, 192.
`
Struct., 1986, 144, 39; ( f ) F. Eugene, B. Langlois and E. Laurent, J. Org.
Chem., 1994, 59, 2599.
16 (a) W. Gerrard, M. F. Lappert and C. A. Pearce, J. Chem. Soc., 1957,
381; (b) I. A. S. Edwards and H. P. Stadler, Acta Crystallogr., Sect. B,
1970, 26, 1905.
3 R. J. Cremlyn, Chlorosulfonic Acid: A Versatile Reagent, Royal Society
of Chemistry, 2002.
17 M. P. Bertrand, Org. Prep. Proced. Int., 1994, 26, 257.
18 (a) W. Nelson and W. Gordy, J. Chem. Phys., 1969, 51, 4710;
(b) K. H. Lau and D. L. Hildenbrand, J. Chem. Phys., 1980, 72, 4928;
(c) Z. L. Cai, Int. J. Quantum Chem., 1993, 45, 295; (d) D. B. Atkinson,
K. K. Irikura and J. W. Hudgens, J. Phys. Chem. A, 1997, 101, 2045.
19 K. Vaughan and M. T. H. Liu, Can. J. Chem., 1981, 59, 923.
20 E. Butcher, C. J. Rhodes and C. Glidewell, J. Chem. Soc., Perkin Trans. 2,
1992, 1461.
¨
4 H. Meerwein, G. Dittmar, R. Gollner, K. Hafner, F. Mensch and
O. Steinfort, Chem. Ber., 1957, 90, 841.
5 (a) E. E. Gilbert, Synthesis, 1969, 3; (b) R. V. Hoffman, Org. Synth., 1981,
60, 121; (c) L. Malet-Sanz, J. Madrzak, S. V. Ley and I. R. Baxendale, Org.
Biomol. Chem., 2010, 8, 5324.
6 (a) D. Zheng, Y. An, Z. Li and J. Wu, Angew. Chem., Int. Ed., 2014,
53, 2451; (b) D. Zheng, Y. Li, Y. An and J. Wu, Chem. Commun., 2014,
DOI: 10.1039/C4CC03032J.
9516 | Chem. Commun., 2014, 50, 9513--9516
This journal is ©The Royal Society of Chemistry 2014