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Organic & Biomolecular Chemistry
Page 4 of 5
COMMUNICATION
Journal Name
structures. In addition,
rearrangement mechanism was also proposed.
a
SO2F2-activated Tiemann
DOI: 10.1039/C9OB01547G
J. Leng, and H.-L. Qin, Eur. J. Org. Chem., 2018, 4407; (c) B.
Gao, L. Zhang, Q. Zheng, F. Zhou, L. M. Klivansky, J. Lu, Y. Liu,
J. Dong, P. Wu and K. B. Sharpless, Nat. Chem., 2017, 9, 1083;
(d) Z. Liu, J. Li, S. Li, G. Li, K. B. Sharpless and P. Wu, J. Am.
Chem. Soc., 2018, 140, 2919; (e) H. Wang, F. Zhou, G. Ren, Q.
Zheng, H. Chen, B. Gao, L. Klivansky, Y. Liu, B. Wu, Q. Xu, J. Lu,
K. B. Sharpless and P.Wu, Angew. Chem.,Int. Ed., 2017, 56,
11203; (f) Q. Zhao, X. Ouyang, X. Wan, K. S. Gajiwala, J. C.
Kath, L. H. Jones, A. L. Burlingame and J.Taunton, J. Am.
Chem. Soc., 2017, 139, 680.
Conflicts of interest
There are no conflicts to declare.
Notes and references
1
(a) A. Kleemann, A. Engel, B. Kutscher and D. Reichert,
Pharmaceutical sustance: Synthesis Patents, Applications,
Georg Thieme, Stuttgart, 4th edn, 2001; (b) A. Ricci, Amino
Group Chemistry From Synthesis to the Life Sciences, Wiley-
VCH, Weinheim, 2008; (c) A. F. Kluge, B. R. Lagu, P. Maiti, M.
Jaleel, M. Webb, J. Malhotra, A. Mallat and P. A. Srinivas,
Bioorg. Med. Chem. Lett., 2018, 28, 2655; (d) J.-P. Falgueyret,
R. M. Oballa, O. Okamoto, G. Wesolowski, Y. Aubin, R. M.
Rydzewski, P. Prasit, D. Riendeau, S. B. Rodan and N. D.
Percival, J. Med. Chem., 2001, 44, 94.
(a) A. G. Gilman, L. S. Goodman, T. W. Rall and F. Murad,
Goodman and Gilman’s The Pharmacological Basis of
Therapeutics, 7th ed.; Pergmon Press: New York, 1990; (b) J.
L. La Mattina, J. Heterocycl. Chem., 1983, 20, 533; (c) T. Cai,
M. Xian and P. G. Wang, Bioorg. Med. Chem. Lett., 2002, 12,
1507; (d) V. Kumar, M. P. Kaushik, A. Mazumdar, Eur. J. Org.
Chem., 2008, 1910; (e) R. W. Stephens, L. A. Domeier, M. G.
Todd and V. A. Nelson, Tetrahedron Lett., 1992, 33, 733.
(a) M. H. Larraufie, G. Maestri, M. Malacria, C. Ollivier, L.
Fensterbank and E. Lacote, Synthesis, 2012, 44, 1279; (b) D.
D. Nekrasov, Russ. J. Org. Chem., 2004, 40, 1387; (c) M. R. R.
Prabhath, L. Williams, S. V. Bhat and P. Sharma, Molecules,
2017, 22, 615.
17 (a) P. S. Hanley, T. P. Clark, A. L. Krasovskiy, M. S. Ober, J. P.
O’Brien and T. S. Staton, ACS Catal., 2016, 6, 3515; (b) S. D.
Schimler, M. A. Cismesia, P. S. Hanley, R. D. J. Froese, M. J.
Jansma, D. C. Bland and M. S. Sanford, J. Am. Chem. Soc.,
2017, 139, 1452; (c) M. Epifanov, P. J. Foth, F. Gu, C. Barrillon,
S. S. Kanani, C. S. Higman, J. E. Hein and G. M. Sammis, J. Am.
Chem. Soc., 2018, 140, 16464; (d) N. Wang, B. Yang, C. Fu, H.
Zhu, F. Zheng, T. Kobayashi, J. Liu, S. Li, C. Ma, P. G. Wang, Q.
Wang and L. Wang, J. Am. Chem. Soc., 2018, 140, 4995; (e) C.
J. Smedley, Q. H. Zheng, B. Gao, S. H. Li, A. Molino, H. M.
Duivenvoorden, B. S. Parker, D. J. D. Wilson, K. B. Sharpless
and J. E. Moses, Angew. Chem., Int. Ed., 2019, 58, 4552; (f) L.
Revathi, L. Ravindar, J. Leng, K. P. Rakesh, and H.-L. Qin,
Asian J. Org. Chem.,2018, 7, 662; (g) W.-Y. Fang, J. Leng and
H.-L. Qin, Chem. Asian J., 2017, 12,2323; (h) C. Zhao, W.-Y.
Fang, K. P. Rakesh and H.-L. Qin, Org. Chem. Front., 2018, 5,
1835; (i) G.-F. Zha, W.-Y. Fang, Y.-G. Li, J. Leng, X. Chen and
H.-L. Qin, J. Am. Chem. Soc., 2018, 140, 17666; (j) G.-F. Zha,
W.-Y. Fang, J. Leng and H.-L. Qin, Adv. Synth. Catal., 2019,
361, 2262.
18 (a) W.-Y. Fang and H.-L. Qin, J. Org. Chem., 2019, 84, 5803; (b)
Y.-Y. Zhao, G.-F. Zhang, C.-R. Ding, Synlett, DOI: 10.1055/s-
0037-1611840.
19 G.-F. Zhang, Y.-Y. Zhao, L.-D. Xuan and C.-R. Ding, Eur. J. Org.
Chem., DOI: 10.1002/ejoc.201900844.
20 R. A. Sheldon, Chem. Soc. Rev., 2012, 41, 1437.
21 (a) K. Sanderson, Nature, 2011, 469, 18; (b) T. Newhouse, P.
S. Baranand R. W. Hoffmann, Chem. Soc. Rev., 2009, 38, 3010;
(c) A. A. Toutov, W.-B. Liu, K. N. Betzl, A. Fedorov,B. M. Stoltz
and R. H. Grubbs, Nature, 2015, 518, 80; (d) Y. Hayashi,
Chem. Sci., 2016, 7, 866.
22 C.-H. Wang, T.-H. Hsieh, C.-C. Lin, W.-H. Yeh, C.-A. Lin and T.-
C. Chien, Synlett, 2015, 26, 1823.
23 S. N. M. Boddapati, N. Polam, B. R. Mutchu and H. B.
Bollikolla, New J. Chem., 2018, 42, 918.
24 H. Basavaprabhu and V. V. Sureshbabu, Org. Biomol. Chem.,
2012, 10, 2528.
2
3
4
(a) J. Van Barun, Ber. Dtsch. Chem. Ges., 1900, 33, 1468; (b)
G. Kaupp, J. Schmeyers and J. Boy, Chem. Eur. J., 1998, 4,
2467.
5
6
W. E. Luttrell, J. Chem. Health Saf., 2009, 16, 29.
(a) R. J. Crutchley, Coord. Chem. Rev., 2001, 219, 125; (b) J. N.
Ayres, M. W. Ashford, Y. Stöckl, V. Prudhomme, K. B. Ling, J.
A. Platts and L. C. Morrill, Org. Lett., 2017, 19, 3835.
(a) R. C. Wheland and E. L. J. Martin, J. Org. Chem., 1975, 40,
3101; (b) Y.-Q. Wu, D. C. Limburg, D. E. Wikinson and G. S.
Hamiton, Org. Lett., 2000, 2, 795; (c) A. M. Van Leusen and J.
C. Jagt, Tetrahedron Lett., 1970, 12, 967; (d) T. V. Hughes, S.
D. Hammond and M. P. J. Cava, J. Org. Chem., 1998, 63, 401;
(e) W. A. Davis and M. P. J. Cava, J. Org. Chem., 1983, 48,
2774.
7
8
9
(a) K. Škoch, I. Cíarová and P. Štěpnicka, Chem. Eur. J., 2018,
24, 13788; (b) C.-Y. Chen, F. F. Wong, J.-J. Huang, S.-K. Lin
and M.-Y. Yeh, Tetrahedron Lett., 2008, 49, 6505.
F. Teng, J.-T. Yu, Y. Jiang, H. Yang and J. Cheng, Chem.
Commun., 2014, 50, 8412.
25 J. Du, K. Luo and X.-L. Zhang, RSC Adv., 2014, 4, 54539.
26 B. Rao and X. M. Zeng, Org. Lett., 2014, 16, 314.
27 Z.-Y. Liao, W.-H. Yeh, P.-Y. Liao, Y.-T. Liu, Y.-C. Chen, Y.-H.
Chen, T.-H. Hsieh, C.-C. Lin, M.-H. Lu, Y.-S. Chen, M.-C. Hsu,
T.-K. Li and T.-C. Chien, Org. Biomol. Chem., 2018, 16, 4482.
28 C.-J. Zeng, C.-J. Chen, C.-W. Chang, H.-T. Chen, and T.-C.
Chien, Aust. J. Chem., 2014, 67, 1134.
10 F. Teng, J.-T. Yu, Z. Zhou, H. Chu, and J. Cheng, J. Org. Chem.,
2015, 80, 2822.
11 C. Zhu, J.-B. Xia and C. Chen, Org. Lett., 2014, 16, 247.
12 G. Talavera, J. Peña and M. Alcarazo, J. Am. Chem. Soc., 2015,
137, 8704.
13 (a) F. Tiemann, Ber. Dtsch. Chem. Ges., 1891, 24, 4162; (b) S.
A. Bakunov, A. V. Rukavishnikov and A. V. Tkachev, Synthesis,
2000, 1148.
14 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.
15 (a) M. P. S. Andersen, D. R. Blake, F. S. Rowland, M. D. Hurley
and T. J. Wallington, Environ. Sci. Technol., 2009, 43, 1067; (b)
SO2F2 is commercially available from chemical vendors world
4 | J. Name., 2012, 00, 1-3
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