Organic Letters
Letter
W.-D.; Yan, X.; Yu, K.-Y.; Fan, C.-A. J. Org. Chem. 2016, 81, 2598.
(f) Gai, K.; Fang, X.; Li, X.; Xu, J.; Wu, X.; Lin, A.; Yao, H. Chem.
Commun. 2015, 51, 15831. (g) Shen, Y.; Qi, J.; Mao, Z.; Cui, S. Org.
Lett. 2016, 18, 2722. (h) Gao, S.; Xu, X.; Yuan, Z.; Zhou, H.; Yao, H.;
Lin, A. Eur. J. Org. Chem. 2016, 2016, 3006. (i) Yang, C.; Gao, S.; Yao,
H.; Lin, A. J. Org. Chem. 2016, 81, 11956. (j) Li, Z.; Chen, Q.; Mayer,
P.; Mayr, H. J. Org. Chem. 2017, 82, 2011. (k) Lin, C.; Shen, Y.;
Huang, B.; Liu, Y.; Cui, S. J. Org. Chem. 2017, 82, 3950. (l) Yuan, Z.;
Wei, W.; Lin, A.; Yao, H. Org. Lett. 2016, 18, 3370. (m) Huang, B.;
Shen, Y.; Mao, Z.; Liu, Y.; Cui, S. Org. Lett. 2016, 18, 4888.
(n) Goswami, P.; Singh, G.; Anand, R. V. Org. Lett. 2017, 19, 1982.
(o) Zhang, X.-Z.; Deng, Y.-H.; Gan, K.-J.; Yan, X.; Yu, K.-Y.; Wang,
F.-X.; Fan, C.-A. Org. Lett. 2017, 19, 1752. (p) Zhuge, R.; Wu, L.;
Quan, M.; Butt, N.; Yang, G.; Zhang, W. Adv. Synth. Catal. 2017, 359,
1028. (q) Arde, P.; Anand, R. V. RSC Adv. 2016, 6, 77111. (r) Zhang,
Z.-P.; Dong, N.; Li, X. Chem. Commun. 2017, 53, 1301. (s) Xie, K.-X.;
Zhang, Z.-P.; Li, X. Org. Lett. 2017, 19, 6708. (t) Vaishanv, N. K.;
Gupta, A. K.; Kant, R.; Mohanan, K. J. Org. Chem. 2018, 83, 8759.
(u) Mei, G.-J.; Xu, S.-L.; Zheng, W.-Q.; Bian, C.-Y.; Shi, F. J. Org.
Chem. 2018, 83, 1414. (v) Zhu, Y. N.; Wang, D.; Huang, Y. Org. Lett.
2019, 21, 908.
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
■
Corresponding Author
ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We are grateful to the NNSFC (Grant No. 21390400) and
Nankai University for financial support. W.Z. thanks Prof. Bin
Chen and Dr. Xu-Zhe Wang at the Technical Institute of
Physics and Chemistry, Chinese Academy of Sciences, for
measuring the quantum yield and fluorescence quenching
experiments. W.Z. also thanks Prof. Jin-Dong Yang at Tsinghua
University for helpful discussions.
(5) Kirste, B.; Harrer, W.; Kurreck, H. J. Am. Chem. Soc. 1985, 107,
20.
(6) Zhao, Y.-N.; Luo, Y.-C.; Wang, Z.-Y.; Xu, P. Chem. Commun.
2018, 54, 3993.
(7) (a) Ke, M.; Song, Q. Adv. Synth. Catal. 2017, 359, 384. (b) Shen,
Y.; Qi, J.; Mao, Z.; Cui, S. Org. Lett. 2016, 18, 2722. (c) Wu, Q.-Y.;
Ao, G.-Z.; Liu, F. Org. Chem. Front. 2018, 5, 2061. (d) Wu, Q.-Y.;
Min, Q.- Q.; Ao, G.-Z.; Liu, F. Org. Biomol. Chem. 2018, 16, 6391.
(e) Wu, Z. J.; Wang, J. Huaxue Xuebao 2017, 75, 74.
(8) Fleming, F. F. Nat. Prod. Rep. 1999, 16, 597.
(9) Fleming, F. F.; Yao, L.; Ravikumar, P. C.; Funk, L.; Shook, B. C.
J. Med. Chem. 2010, 53, 7902.
REFERENCES
■
̈
(1) (a) Abrams, P.; Freeman, R.; AnderstrOm, C.; Mattiasson, A.
BJU Int. 1998, 81, 801. (b) Davidson, S. J.; Barker, D. Tetrahedron
Lett. 2015, 56, 4549. (c) Altenbach, R. J.; Black, L. A.; Strakhova, M.
I.; Manelli, A. M.; Carr, T. L.; Marsh, K. C.; Wetter, J. M.; Wensink,
E. J.; Hsieh, G. C.; Honore, P.; Garrison, T. R.; Brioni, J. D.; Cowart,
M. D. J. Med. Chem. 2010, 53, 7869. (d) Shah, J. R.; Mosier, P. D.;
Roth, B. L.; Kellogg, G. E.; Westkaemper, R. B. Bioorg. Med. Chem.
2009, 17, 6496. (e) Song, F.; Lu, S.; Gunnet, J.; Xu, J. Z.; Wines, P.;
Proost, J.; Liang, Y.; Baumann, C.; Lenhard, J. W.; Murray, V.;
Demarest, K. T.; Kuo, G.-H. J. Med. Chem. 2007, 50, 2807.
(10) For a review on radical-initiated functionalization of alkyl
nitriles, see: Chu, X.-Q.; Ge, D.; Shen, Z.-L.; Loh, T.-P. ACS Catal.
2018, 8, 258.
(11) For selected recent examples for radical cyanomethylation, see:
(a) He, T.-J.; Ye, Z. R.; Ke, Z. F.; Huang, J.-M. Nat. Commun. 2019,
Song, R.-J.; Li, J.-H. Chem. Commun. 2018, 54, 12345. (c) Qiao, K.;
Zhang, D.; Zhang, K.; Yuan, X.; Zheng, M.-W.; Guo, T.-F.; Fang, Z.;
Wan, L.; Guo, K. Org. Chem. Front. 2018, 5, 1129. (d) Zhang, W.;
Yang, C.; Pan, Y.-L.; Li, X.; Cheng, J.-P. Org. Biomol. Chem. 2018, 16,
5788. (e) Zhang, R.; Jin, S.; Liu, Q.; Lin, S.; Yan, Z. J. J. Org. Chem.
2018, 83, 13030. (f) Su, H.-M.; Wang, L.-Y.; Rao, H.-H.; Xu, H. Org.
Lett. 2017, 19, 2226. (g) Welin, E. R.; Warkentin, A. A.; Conrad, J. C.;
MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 9668.
(h) Bunescu, A.; Wang, Q.; Zhu, J. Org. Lett. 2015, 17, 1890.
(i) Chatalova-Sazepin, C.; Wang, Q.; Sammis, G. M.; Zhu, J. Angew.
Chem., Int. Ed. 2015, 54, 5443. (j) Bunescu, A.; Wang, Q.; Zhu, J.
Angew. Chem., Int. Ed. 2015, 54, 3132.
(2) For a review on catalytic asymmetric reactions of p-QMs, see: Li,
W.; Xu, X.; Zhang, P.; Li, P. Chem. - Asian J. 2018, 13, 2350.
(3) For pioneer examples of catalytic asymmetric reactions of p-
QMs: (a) Chu, W.-D.; Zhang, L.-F.; Bao, X.; Zhao, X.-H.; Zeng, C.;
Du, J.-Y.; Zhang, G.-B.; Wang, F.-X.; Ma, X.-Y.; Fan, C.-A. Angew.
Chem., Int. Ed. 2013, 52, 9229. (b) Caruana, L.; Kniep, F. T.;
Johansen, K.; Poulsen, P. H.; Jørgensen, K. A. J. Am. Chem. Soc. 2014,
136, 15929. (c) Wang, Z.; Wong, Y. F.; Sun, J. Angew. Chem., Int. Ed.
2015, 54, 13711. (d) Lou, Y.; Cao, P.; Jia, T.; Zhang, Y.; Wang, M.;
Liao, J. Angew. Chem., Int. Ed. 2015, 54, 12134. (e) Dong, N.; Zhang,
Z.-P.; Xue, X.-S.; Li, X.; Cheng, J.-P. Angew. Chem., Int. Ed. 2016, 55,
1460. (f) Zhao, K.; Zhi, Y.; Wang, A.; Enders, D. ACS Catal. 2016, 6,
657. (g) Li, X.; Xu, X.; Wei, W.; Lin, A.; Yao, H. Org. Lett. 2016, 18,
428. (h) Zhao, K.; Zhi, Y.; Shu, T.; Valkonen, A.; Rissanen, K.;
Enders, D. Angew. Chem., Int. Ed. 2016, 55, 12104. (i) Jarava-Barrera,
(12) For recent examples about the radical ring opening of
cyclobutanone oxime derivatives, see: (a) Zhang, J.-J.; Duan, X.-H.;
Wu, Y.; Yang, J.-C.; Guo, L.-N. Chem. Sci. 2019, 10, 161. (b) Wang,
P.-Z.; Yu, X.-Y.; Li, C.-Y.; He, B.-Q.; Chen, J.-R.; Xiao, W.-J. Chem.
́
C.; Parra, A.; Ljpez, A.; Cruz-Acosta, F.; Collado-Sanz, D.; Cardenas,
D. J.; Tortosa, M. ACS Catal. 2016, 6, 442. (j) He, F.-S.; Jin, J.-H.;
Yang, Z.-T.; Yu, X.; Fossey, J. S.; Deng, W.-P. ACS Catal. 2016, 6,
652. (k) Ma, C.; Huang, Y.; Zhao, Y. ACS Catal. 2016, 6, 6408.
(l) Liu, Q.; Li, S.; Chen, X.-Y.; Rissanen, K.; Enders, D. Org. Lett.
2018, 20, 3622. (m) Jiang, F.; Yuan, F.-R.; Jin, L.-W.; Mei, G.-J.; Shi,
F. ACS Catal. 2018, 8, 10234. (n) Zhang, L.; Liu, Y.; Liu, K.; Liu, Z.;
He, N.; Li, W. Org. Biomol. Chem. 2017, 15, 8743. (o) Zhang, L.;
Yuan, H.; Lin, W.; Cheng, Y.; Li, P.; Li, W. Org. Lett. 2018, 20, 4970.
(p) Li, W.; Yuan, H.; Liu, Z.; Zhang, Z.; Cheng, Y.; Li, P. Adv. Synth.
Catal. 2018, 360, 2460. (q) Sun, Z.; Sun, B.; Kumagai, N.; Shibasaki,
M. Org. Lett. 2018, 20, 3070.
Commun. 2018, 54, 9925. (c) Yin, Z. P.; Rabeah, J.; Bruckner, A.; Wu,
̈
X.-F. ACS Catal. 2018, 8, 10926. (d) Yu, X.-Y.; Zhao, Q.-Q.; Chen, J.;
Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2018, 57, 15505.
(e) Yu, X.-Y.; Wang, P.-Z.; Yan, D.-M.; Lu, B.; Chen, J.-R.; Xiao, W.-J.
Adv. Synth. Catal. 2018, 360, 3601. (f) Zhao, J.-F.; Gao, P.; Duan, X.-
H.; Guo, L.-N. Adv. Synth. Catal. 2018, 360, 1775. (g) Dauncey, E.
M.; Morcillo, S. P.; Douglas, J. J.; Sheikh, N. S.; Leonori, D. Angew.
Chem., Int. Ed. 2018, 57, 744. (h) Yu, X.-Y.; Chen, J.-R.; Wang, P.-Z.;
Yang, M.-N.; Liang, D.; Xiao, W.-J. Angew. Chem., Int. Ed. 2018, 57,
738. (i) Zhao, J.-F.; Duan, X.-H.; Gu, Y.-R.; Gao, P.; Guo, L.-N. Org.
Lett. 2018, 20, 4614. (j) Shen, X.; Zhao, J.-J.; Yu, S. Y. Org. Lett. 2018,
20, 5523. (k) Le Vaillant, F.; Garreau, M.; Nicolai, S.; Gryn’ova, G.;
Corminboeuf, C.; Waser, J. Chem. Sci. 2018, 9, 5883. (l) Yang, L.;
Gao, P.; Duan, X.-H.; Gu, Y.-R.; Guo, L.-N. Org. Lett. 2018, 20, 1034.
(4) For selected recent examples of catalytic symmetric reactions of
p-QMs, see: (a) Yuan, Z.; Fang, X.; Li, X.; Wu, J.; Yao, H.; Lin, A. J.
Org. Chem. 2015, 80, 11123. (b) Ramanjaneyulu, B. T.; Mahesh, S.;
Anand, R. V. Org. Lett. 2015, 17, 3952. (c) Reddy, V.; Anand, R. V.
Org. Lett. 2015, 17, 3390. (d) Arde, P.; Anand, R. V. Org. Biomol.
Chem. 2016, 14, 5550. (e) Zhang, X.-Z.; Du, J.-Y.; Deng, Y.-H.; Chu,
E
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