10.1002/ejoc.201900844
European Journal of Organic Chemistry
COMMUNICATION
General
procedure
for
the
SO2F2-promoted
Beckmann
[10] X. Mo, T. D. R. Morgan, H. T. Ang, D. G. Hall, J. Am. Chem. Soc. 2018,
140, 5264.
Rearrangement of ketoximes to amides/lactams. Oxime substrates 1
(1.0 mmol, 1.0 equiv), Et3N (278 uL, 2.0 mmol, 2.0 equiv) and CH3CN
(5.0 mL, 0.2 M) were sequentially added into an oven-dried reaction tube
(30 mL) equipped with a stirring bar, the reaction tube was covered with
a plastic stopper before the SO2F2 gas was introduced into the stirring
reaction mixture by slow bubbling through a SO2F2 balloon at the room
temperature for 30 min. Then, 5% hydrochloric acid (1.0 mL, 1.35 mmol,
1.35 equiv) was added into the mixture and stirred at the room
temperature for an additional 15 min. After that, the reaction diluted with
water and extracted with dichloromethane (3× 20 mL). Then the
combined organic layers were washed with brine, dried over anhydrous
Na2SO4, and concentrated to dryness. The residue was purified through
silica gel chromatography using a mixture of ethyl acetate and petroleum
ether as eluent to afford the desired amides or lactams 2.
[11] P. S. Mahajan, V. T. Humne, S. D. Tanpure, S. B. Mhaske, Org. Lett.
2016, 18, 3450.
[12] V. P. Srivastava, A. K. Yadav, L. D. S. Yadav, Synlett 2014, 665.
[13] a) K. Sanderson, Nature 2011, 469, 18; b) A. A. Toutov, W.-B. Liu, K. N.
Betz, A. Fedorov, B. M. Stoltz, R. H. Grubbs, Nature 2015, 518, 80.
[14] M. P. Sulbaek Andersen, D. R. Blake, F. S. Rowland, M. D. Hurley, T. J.
Wallington, Environ. Sci. Technol. 2009, 43, 1067.
[15] J. Dong, L. Krasnova, M. G. Finn, K. B. Sharpless, Angew. Chem., Int.
Ed. 2014, 53, 9430.
[16] For some selected examples on SuFEx chemistry, see: a) B. Gao, L.
Zhang, Q. Zheng, F. Zhou, L. M. Klivansky, J. Lu, Y. Liu, J. Dong, P.
Wu, K. B. Sharpless, Nat. Chem. 2017, 9, 1083; b) 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, P. Wu, Angew. Chem., Int. Ed. 2017, 56, 11203;
c) Q. Zhao, X. Ouyang, X. Wan, K. S. Gajiwala, J. C. Kath, L. H. Jones,
A. L. Burlingame, J. Taunton, J. Am. Chem. Soc. 2017, 139, 680; d) Z.
Liu, J. Li, S. Li, G. Li, K. B. Sharpless, P. Wu, J. Am. Chem. Soc. 2018,
140, 2919; e) S. Wang, B. Moku, J. Leng, H.-L. Qin, Eur. J. Org. Chem.
2018, 4407.
Acknowledgments
We acknowledge financial support from the National Natural
Science Foundation of China (no. 20702051), the Natural
Science Foundation of Zhejiang Province (LY13B020017).
[17] For reviews of SO2F2 utilization, see: a) L. Revathi, L. Ravindar, J. Leng,
K. P. Rakesh, H.-L. Qin, Asian J. Org. Chem. 2018, 7, 662; For some
selected examples, see: b) P. S. Hanley, T. P. Clark, A. L. Krasovskiy,
M. S. Ober, J. P. O’Brien, T. S. Staton, ACS Catal. 2016, 6, 3515; c) S.
D. Schimler, M. A. Cismesia, P. S. Hanley, R. D. J. Froese, M. J.
Jansma, D. C. Bland, M. S. Sanford, J. Am. Chem. Soc. 2017, 139,
1452; d) W.-Y. Fang, J. Leng, H.-L. Qin, Chem. Asian J. 2017, 12, 2323;
e) M. Epifanov, P. J. Foth, F. Gu, C. Barrillon, S. S. Kanani, C. S.
Higman, J. E. Hein, G. M. Sammis, J. Am. Chem. Soc. 2018, 140,
16464; f) C. Zhao, W.-Y. Fang, K. P. Rakesh, H.-L. Qin, Org. Chem.
Front. 2018, 5, 1835; g) G.-F. Zha, W.-Y. Fang, Y.-G. Li, J. Leng, X.
Chen, H.-L. Qin, J. Am. Chem. Soc. 2018, 140, 17666; h) N. Wang, B.
Yang, C. Fu, H. Zhu, F. Zheng, T. Kobayashi, J. Liu, S. Li, C. Ma, P. G.
Wang, Q. Wang, L. Wang, J. Am. Chem. Soc. 2018, 140, 4995; i) 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, J. E.
Moses, Angew. Chem., Int. Ed. 2019, 58, 4552; j) G.-F. Zha, W.-Y.
Keywords: Sulfuryl fluoride • Beckmann rearrangement •
Ketoximes • Amides • Sulfonyl ester
[1]
[2]
[3]
[4]
a) E. Ber. Beckmann, Dtsch. Chem. Ges. 1886, 19, 988; b) A. H. Blatt,
Chem. Rev. 1933, 12, 215.
a) R. E. Gawley, Org. React. 1988, 35, 14; b) M. T. Nguyen, G.
Raspoet, L. G. Vanquickenborne, J. Am. Chem. Soc. 1997, 119, 2552.
a) B. Jones, Chem. Rev. 1944, 35, 335; b) B. Jones, Nature 1946, 157,
519.
a) K. Weissermel, H. J. Arpe, Industrial Organic Chemistry, 4th ed.,
Wiley-VCH Verlag GmbH: Weinheim, Germany, 2003; b) K. You, L.
Mao, D. Yin, P. Liu, H. A. Luo, Catal. Commun. 2008, 9, 1521; c) F.
Aricò, G. Quartarone, E. Rancan, L. Ronchin, P. Tundo, A. Vavasori,
Catal. Commun. 2014, 49, 47; d) L. R. Jefferies, S. R. Weber, S. P.
Cook, Synlett 2015, 26, 331.
Fang,
J.
Leng,
H.-L.
Qin,
Adv.
Synth.
Catal.
DOI:
10.1002/adsc.201900104.
[18] a) W.-Y. Fang, H.-L. Qin, J. Org. Chem. DOI: 10.1021/acs.joc.8b03164;
b) Y.-Y. Zhao, G.-F. Zhang, C.-R. Ding, Synlett 2019, just accepted.
[19] R. A. Sheldon, Chem. Soc. Rev. 2012, 41, 1437.
[5]
[6]
a) R. E. Gawley, in Organic Reactions, John Wiley & Sons, Inc., Vol. 35,
1988, pp. 1; b) S. Chandrasekhar, In Comprehensive Organic
Synthesis II; P. Knochel, G. A. Molander, Eds.; Elsevier: Amsterdam,
Vol. 7, 2014, pp. 770.
[20] T.-J. Guo, G.-Y. Meng, X.-J. Zhan, Q. Yang, T.-C. Ma, L. Xu, K. B.
Sharpless, J.-J. Dong, Angew. Chem., Int. Ed. 2018, 57, 2605.
[21] a) C. M. Vanos, T. H. Lambert, Chem. Sci. 2010, 1, 705; b) N. An, B.-X.
Tian, H.-J. Pi, L. A. Eriksson, W.-P. Deng, J. Org. Chem. 2013, 78,
4297; c) H.-J. Pi, J.-D. Dong, N. An, W. Du, W.-P. Deng, Tetrahedron
2009, 65, 7790.
Y. Furuya, K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 2005, 127,
11240.
[7]
[8]
C. M. Vanos, T. H. Lambert, Chem. Sci. 2010, 1, 705.
Y. Gao, J. Liu, Z. Li, T. Guo, S. Xu, H. Zhu, F. Wei, S. Chen, H. Gebru,
K. Guo, J. Org. Chem. 2018, 83, 2040.
[22] a) P. Starkov, T.D. Sheppard, Org. Biomol. Chem. 2011, 9, 1320; b) G.-
Z. Sheng, W. Zhang, Chin. J. Org. Chem. 2013, 33, 2271.
[9]
a) M. Zhu, C. Cha, W.-P. Deng, X.-X. Shi, Tetrahedron Lett. 2006, 47,
4861; b) M. Hashimoto, Y. Obora, S. Sakaguchi, Y. Ishii, J. Org. Chem.
2008, 73, 2894; c) H.-J. Pi, J.-D. Dong, N. An, W. Du, W.-P. Deng,
Tetrahedron 2009, 65, 7790; d) V. P. Srivastava, R. Patel, Garima, L. D.
S. Yadav, Chem. Commun. 2010, 46, 5808; e) J. K. Augustine, R.
Kumar, A. Bombrun, A. B. Mandal, Tetrahedron Lett. 2011, 52, 1074; f)
F. Xie, C. Du, Y. Pang, X. Lian, C. Xue, Y. Chen, X. Wang, M. Cheng,
C. Guo, B. Lin, Y. Liu, Tetrahedron Lett. 2016, 57, 5820.
[23] a) B.-X. Tian, N. An, W.-P. Deng, L. A. Eriksson, J. Org. Chem. 2013,
78, 6782; b) R. Akimoto, T. Tokugawa, Y. Yamamoto, H. Yamataka, J.
Org. Chem. 2012, 77, 4073; c) H. J. Kiely-Collins, I. Sechi, P. E.
Brennan, M. G. McLaughlin, Chem. Commun. 2018, 54, 654.
This article is protected by copyright. All rights reserved.