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ChemComm
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DOI: 10.1039/C7CC09871E
COMMUNICATION
Journal Name
radical alkene hydroamination of unsaturated sulfonamides, we
Leonori, J. Am. Chem. Soc., 2016, 138, 8092-8095; (e) E.
Brachet, L. Marzo, M. Selkti, B. König and P. Belmont, Chem.
subjected the enantiopure (R)-1b to the standard conditions
Sci., 2016,
and D. A. Nagib, J. Am. Chem. Soc., 2017, 139, 10204-10207;
g) H. Jiang and A. Studer, Angew. Chem. Int. Ed., 2017, 56
12273-12276; (h) E. Ito, T. Fukushima, T. Kawakami, K.
Murakami and K. Itami, Chem, 2017, , 383-392; (i) J. Davies,
N. S. Sheikh and D. Leonori, Angew. Chem. Int. Ed., 2017, 56
3361-13365; (j) Q. Zhu, D. E. Graff and R. R. Knowles, J. Am.
Chem. Soc., 2018, 140, 741-747.
(a) X.-Q. Hu, J.-R. Chen, Q. Wei, F.-L. Liu, Q.-H. Deng, A. M.
Beauchemin and W.-J. Xiao, Angew. Chem. Int. Ed., 2014, 53
7, 5002-5006; (f) E. A. Wappes, K. M. Nakafuku
(Scheme 4). The expected reaction proceeded smoothly to give
product 2b as a single diastereomer in 57% yield with >99% ee. The
absolute configuration of 2b was unambiguously determined to be
(
,
1
1
(
3R, 5R) by X-ray crystallography, indicating that the labile
2
,
benzylic stereocenter was not affected.
1
4
,
12163-12167; (b) X.-Q. Hu, X. Qi, J.-R. Chen, Q.-Q. Zhao, Q.
Wei, Y. Lan and W.-J. Xiao, Nat. Commun., 2016, 7, 11188; (c)
X.-Q. Hu, J. Chen, J.-R. Chen, D.-M. Yan and W.-J. Xiao, Chem.
Eur. J., 2016, 22, 14141-14146; (d) Q.-Q. Zhao, X. Q. Hu, M.-
N. Yang, J.-R. Chen and W.-J. Xiao, Chem. Commun., 2016,
52, 12749-12752; (e) Q.-Q. Zhao, J. Chen, D.-M. Yan, J.-R.
Chen and W.-J. Xiao, Org. Lett., 2017, 19, 3620-3623; (f) X.-Y.
Yu, F. Zhou, J.-R. Chen and W.-J. Xiao, Acta Chim. Sinica,
Scheme
4 Enantioselective version of visible light-driven
photocatalytic alkene hydroamination.
2
017, 75, 86-91; (g) X.-Y. Yu, J.-R. Chen, P.-Z. Wang, M.-N.
In summary, we have described
a
visible light-driven
Yang, D. Liang and W.-J. Xiao, Angew. Chem. Int. Ed., 2018,
57, 738-743.
For selected reviews, see: (a) J. Cornil, L. Gonnard, C.
Bensoussan, A. Serra-Muns, C. Gnamm, C. Commandeur, M.
Commandeur, S. Reymond, A. Guerinot and J. Cossy, Acc.
Chem. Res., 2015, 48, 761-773; (b) M. Berthet, T. Cheviet, G.
photocatalytic generation of sulfonamidyl radicals for the first time.
These radical species enable development of an intramolecular
radical alkene hydroamination reaction, providing a mild and
efficient approach to various valuable functionalized isoxazolidines.
Further application of the current protocol to activation of other N-
H bonds into NCRs is currently underway.
5
Dujardin, I. Parrot and J. Martinez, Chem. Rev., 2016, 116
,
15235-15283; (c) D. Li, Y. Wu, H. Chang, W. Gao, W. Wei and
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We are grateful to the NNSFC (Nos. 21622201, 21472058,
2
1472057, and 21772053), the Distinguished Youth
Foundation of Hubei Province (No. 2016CFA050), and CCNU
Nos. CCNU17TS0011 and CCNU16JCZX02) for support of this
(
research. The Program of Introducing Talents of Discipline to
Universities of China (111 Program, B17019) is also
appreciated.
5
, 2723-2726.
6
7
(a) S. D. Karyakarte, T. P. Smith and S. R. Chemler, J. Org.
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Notes and references
1
For selected recent reviews on visible light photocatalysis,
see: (a) C. K. Prier, D. A. Rankic and D. W. MacMillan, Chem.
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6
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8
,
2
017,
1, 148-158; (i) Q. Liu and L.-Z. Wu, Natl. Sci. Rev., 2017,
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193-5203.
Please see the ESI for more details.
0 For selected reviews on alkene hydroamination, see: (a) S. R.
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Bernoud, C. Lepori, M. Mellah, E. Schulz and J. Hannedouche,
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9
1
2
3
For selected reviews on the N-radical chemistry, see: (a) S. Z.
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8
1
1
1 CCDC 1588081 (2a) and 1813075 ((3R, 5R)-2b) (ESI†).
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