Organic Letters
Letter
22
F− anion or HF, which could be further absorbed by
Res. 2013, 46, 236−247. (g) Guo, X.; Hu, W. Acc. Chem. Res. 2013,
46, 2427−2440. (h) Ford, A.; Miel, H.; Ring, A.; Slattery, C. N.;
Ca(OH) to afford CaF .
2
2
Maguire, A. R.; McKervey, M. A. Chem. Rev. 2015, 115, 9981−10080.
In summary, we have developed a catalyst-free gem-
aminoselenolation of fluoroalkyl-substituted nonconjugated
diazo compounds with diselenides and NFSI to yield a unique
type of compounds containing nitrogen, selenium, and fluoride
atoms. Diaryl and dialkyl diselenides, as well as disulfide and
ditelluride, were all suitable substrates for this gem-difunction-
alization. Besides fluoroalkyl-substituted nonconjugated diazo
compounds, different types of conjugated diazo compounds
can also be used for this transformation. Preliminary
mechanistic studies indicate that a selenoimidate intermediate
generated from diselenide and NFSI is involved for this
transformation. Efforts on expanding this strategy to other
types of gem-difunctionalization of fluoroalkyl substituted
nonconjugated diazo compounds are ongoing.
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ASSOCIATED CONTENT
Supporting Information
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*
S
(
f) Ye, F.; Qu, S.; Zhou, L.; Peng, C.; Wang, C.; Cheng, J.; Hossain,
M. L.; Liu, Y.; Zhang, Y.; Wang, Z.-X.; Wang, J. J. Am. Chem. Soc.
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Experimental procedure and spectroscopic data for all
(5) (a) Tao, J.; Tran, R.; Murphy, G. K. J. Am. Chem. Soc. 2013, 135,
Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
16312−16315. (b) Liu, W.-J.; Lv, B.-D.; Gong, L.-Z. Angew. Chem.
2009, 121, 6625−6628. (c) Li, H.; Wang, L.; Zhang, Y.; Wang, J.
Angew. Chem. 2012, 124, 2997−3000. (d) Li, H.; Shangguan, X.;
Zhang, Z.; Huang, S.; Zhang, Y.; Wang, J. Org. Lett. 2014, 16, 448−
4
51. (e) Mao, H.; Tang, Z.; Hu, H.; Cheng, Y.; Zheng, W.-H.; Zhu, C.
Chem. Commun. 2014, 50, 9773−9775. (f) Chen, G.; Song, J.; Yu, Y.;
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(6) (a) Ovalles, S. R.; Hansen, J. H.; Davies, H. M. L. Org. Lett.
AUTHOR INFORMATION
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2011, 13, 4284−4287. (b) Zheng, Y.; Bian, R.; Zhang, X.; Yao, R.;
Qiu, L.; Bao, X.; Xu, X. Eur. J. Org. Chem. 2016, 2016, 3872−3877.
(7) (a) Mykhailiuk, P. K.; Afonin, S.; Palamarchuk, G. V.; Shishkin,
*
O. V.; Ulrich, A. S.; Komarov, I. V. Angew. Chem., Int. Ed. 2008, 47,
*
5
765−5767. (b) Morandi, B.; Carreira, E. M. Angew. Chem., Int. Ed.
ORCID
2
010, 49, 938−941. (c) Morandi, B.; Mariampillai, B.; Carreira, E. M.
Notes
Angew. Chem., Int. Ed. 2011, 50, 1101−1104.
(
8) Morandi, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49,
294−4296.
9) (a) Liu, C.-B.; Feng, W.; Li, F.; Wang, S.; Nie, J.; Ma, J.-A.
4
(
The authors declare no competing financial interest.
Angew. Chem., Int. Ed. 2012, 51, 6227−6230. (b) Luo, H.; Wu, G.;
Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2015, 54, 14503−14507.
(10) (a) Li, F.; Nie, J.; Sun, L.; Zheng, Y.; Ma, J.-A. Angew. Chem.,
Int. Ed. 2013, 52, 6255−6258. (b) Qin, S.; Zheng, Y.; Zhang, F.-G.;
Ma, J.-A. Org. Lett. 2017, 19, 3406−3409. (c) Chen, Z.; Zheng, Y.;
Ma, J.-A. Angew. Chem., Int. Ed. 2017, 56, 4569−4574.
ACKNOWLEDGMENTS
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Financial support from NSF of China (21772043) are greatly
acknowledged. We also acknowledge the financial support
from Guangdong Innovative and Entrepreneurial Research
Team Program (No. 2016ZT06Y337).
(11) (a) Ma, C.; Xing, D.; Zhai, C.; Che, J.; Liu, S.; Wang, J.; Hu, W.
Org. Lett. 2013, 15, 6140−6143. (b) Yang, Y.; Ma, C.; Thumar, N. J.;
Hu, W. J. Org. Chem. 2016, 81, 8537−8543. (c) Ma, C.; Xing, D.; Hu,
W. Org. Lett. 2016, 18, 3134−3137. (d) Xiao, G.; Ma, C.; Xing, D.;
Hu, W. Org. Lett. 2016, 18, 6086−6089. (e) Ma, C.; Chen, J.; Xing,
D.; Sheng, Y.; Hu, W. Chem. Commun. 2017, 53, 2854−2857. (f) Jia,
S.; Xing, D.; Zhang, D.; Hu, W. Angew. Chem., Int. Ed. 2014, 53,
13098−13101.
(12) For selected reviews, see: (a) Mailyan, A. K.; Eickhoff, J. A.;
Minakova, A. S.; Gu, Z.; Lu, P.; Zakarian, A. Chem. Rev. 2016, 116,
4441−4557. (b) Bariwal, J.; Eycken, E. V. Chem. Soc. Rev. 2013, 42,
9283−9303. (c) Ledesma, M. C.; Jung-Hynes, B.; Schmit, T. L.;
Kumar, R.; Mukhtar, H.; Ahmad, N. Mol. Med. 2011, 17, 134−143.
(d) Naithani, R. Mini-Rev. Med. Chem. 2008, 8, 657−668.
(e) Nogueira, C. W.; Zeni, G.; Rocha, J. B. T. Chem. Rev. 2004,
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