Organic Letters
Letter
(10) (a) Liu, B.-Q.; Fan, Y.; Gao, Y.; Sun, C.; Xu, C.; Zhu, J. J. Am.
Chem. Soc. 2013, 135, 468. (b) Chen, J.-S.; Chen, P.; Song, C.; Zhu, J.
Chem. - Eur. J. 2014, 20, 14245. (c) Gao, T.-T.; Sun, P.-P. J. Org.
Chem. 2014, 79 (20), 9888. (d) Xie, F.; Qi, Z.-S.; Yu, S.-J.; Li, X.-W. J.
Am. Chem. Soc. 2014, 136, 4780. (e) Li, D.-D.; Cao, Y.-X.; Wang, G.-
W. Org. Biomol. Chem. 2015, 13, 6958. (f) Wu, Y.-N.; Sun, L.; Chen,
Y.-Y.; Zhou, Q.; Huang, J.-W.; Miao, H.; Luo, H.-B. J. Org. Chem.
2016, 81, 1244. (g) Tian, M.-M.; Yang, X.-F.; Zhang, B.; Liu, B.-X.;
Li, X.-W. Org. Chem. Front. 2018, 5, 3406. (h) He, S.; Tan, G.-Y.; Luo,
A.-P.; You, J.-S. Chem. Commun. 2018, 54, 7794.
(11) (a) Challis, B. C.; Challis, J. A. N-Nitrosamines and N-
Nitrosoimines. In The Chemistry of Amino, Nitroso and Nitro
Compounds and Their Derivatives; Patai, S., Ed.; John Wiley & Sons:
Chichester, U.K., 1982; pp 1151−1223. (b) Klein, D. Organic
Chemistry; John Wiley & Sons: Hoboken, NJ, 2012.
(12) Wu, Y.-N.; Feng, L.-J.; Lu, X.; Kwong, F. Y.; Luo, H.-B. Chem.
Commun. 2014, 50, 15352.
(13) (a) Liu, B.-Q.; Song, C.; Sun, C.; Zhou, S.-G.; Zhu, J. J. Am.
Chem. Soc. 2013, 135, 16625. (b) Liang, Y.-J.; Jiao, N. Angew. Chem.
2016, 128, 4103. (c) Wang, H.-N.; Li, S.-Q.; Wang, B.-Q.; Li, B. Org.
Chem. Front. 2018, 5, 88. (d) Song, X.; Gao, C.; Li, B.; Zhang, X.-Y.;
Fan, X.-S. J. Org. Chem. 2018, 83, 8509.
(14) (a) Wang, J.; Wang, M.-Y.; Chen, K.-H.; Zha, S.-K.; Song, C.;
Zhu, J. Org. Lett. 2016, 18, 1178. (b) Hu, X.-W.; Chen, X.; Shao, Y.-
X.; Xie, H.-S.; Deng, Y.-F.; Ke, Z.-F.; Jiang, H.-F.; Zeng, W. ACS
Catal. 2018, 8, 1308.
(15) Dong, J.-W.; Wu, Z.-J.; Liu, Z.-Y.; Liu, P.; Sun, P.-P. J. Org.
Chem. 2015, 80 (24), 12588.
(16) (a) Rossetti, M.; Stipa, P.; Petrucci, R.; Greci, L. J. Chem. Res.,
Synop. 1999, 362. (b) Chen, W.-L.; Wu, S.-Y.; Mo, X.-L.; Wei, L.-X.;
Liang, C.; Mo, D.-L. Org. Lett. 2018, 20, 3527. (c) Shoberu, A.; Li, C.-
K.; Tao, Z.-K.; Zhang, G.-Y.; Zou, J.-P. Adv. Synth. Catal. 2019, 361,
2255.
(18) Molander, G. A.; Cavalcanti, L. N. J. Org. Chem. 2012, 77,
4402.
ACKNOWLEDGMENTS
■
We gratefully acknowledge partial financial support from the
Ministry of Science and Technology of China
(2016YFE0132600) and Zhengzhou University.
REFERENCES
■
(1) (a) Bru
̈
ckl, T.; Baxter, R. D.; Ishihara, Y.; Baran, P. S. Acc. Chem.
Res. 2012, 45, 826−839. (b) Song, W.; Ackermann, L. Chem.
Commun. 2013, 49, 6638−6640. (c) Liu, W.; Ackermann, L. ACS
Catal. 2016, 6, 3743. (d) He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.;
Yu, J.-Q. Chem. Rev. 2017, 117, 8754. (e) Park, Y.; Kim, Y.; Chang, S.
Chem. Rev. 2017, 117, 9247. (f) Xia, Y.; Qiu, D.; Wang, J.-B. Chem.
̈
Rev. 2017, 117, 13810−13889. (g) Sambiagio, C.; Schonbauer, D.;
Blieck, R.; et al. Chem. Soc. Rev. 2018, 47, 6603−6743.
(2) (a) Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J.
Am. Chem. Soc. 2004, 126, 2706−2707. (b) Peng, J.-L.; Xie, Z.-Q.;
Chen, M.; Wang, J.; Zhu, Q. Org. Lett. 2014, 16, 4702−4705.
(c) Zhang, C.; Rao, Y. Org. Lett. 2015, 17, 4456−4459.
(d) Bettadapur, K. R.; Lanke, V.; Prabhu, K. R. Org. Lett. 2015, 17,
4658−4661. (e) Ogiwara, Y.; Miyake, M.; Kochi, T.; Kakiuchi, F.
Organometallics 2017, 36, 159−164. (f) Zhang, B.; Wang, H.-W.;
Kang, Y.-S.; Zhang, P.; Xu, H.-J.; Lu, Y.; Sun, W.-Y. Org. Lett. 2017,
19, 5940−5943. (g) Xu, F.; Li, Y.-J.; Huang, C.; Xu, H. C. ACS Catal.
2018, 8, 3820.
(3) (a) Liu, X.; Li, X.; Liu, H.; Guo, Q.; Lan, J.; Wang, R.; You, J.
Org. Lett. 2015, 17, 2936−2939. (b) Mo, J.; Wang, L.; Cui, X. Org.
Lett. 2015, 17, 4960−4963. (c) Luo, J.; Preciado, S.; Araromi, S. O.;
Larrosa, I. Chem. - Asian J. 2016, 11, 347−350. (d) Kumar, N. Y. P.;
Bechtoldt, A.; Raghuvanshi, K.; Ackermann, L. Angew. Chem., Int. Ed.
2016, 55, 6929−6932. (e) Zhang, J.; Shrestha, R.; Hartwig, J. F.;
Zhao, P. Nat. Chem. 2016, 8, 1144−1151. (f) Wu, J.-Q.; Zhang, S.-S.;
Gao, H.; Qi, Z.; Zhou, C.-J.; Ji, W.-W.; Liu, Y.; Chen, Y.; Li, Q.; Li, X.;
Wang, H. J. Am. Chem. Soc. 2017, 139, 3537−3545.
(4) (a) Wu, J.; Cui, X.; Chen, L.; Jiang, G.; Wu, Y. J. Am. Chem. Soc.
2009, 131, 13888. (b) Zhang, Z.-H.; Pi, C.; Tong, H.; Cui, X.; Wu, Y.
Org. Lett. 2017, 19, 440.
(5) (a) Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 3676.
(b) Liu, G. X.; Shen, Y.-Y.; Zhou, Z.; Lu, X.-Y. Angew. Chem., Int. Ed.
2013, 52, 6033. (c) Zhou, Z.; Liu, G.; Shen, Y.; Lu, X. Org. Chem.
Front. 2014, 1, 1161. (d) Zhou, J.; Shi, J.-J.; Qi, Z.-S.; Li, X.-W.; Xu,
H.-E.; Yi, W. ACS Catal. 2015, 5 (11), 6999. (e) Huang, X.; Liang,
W.; Shi, Y.; You, J. Chem. Commun. 2016, 52, 6253.
(6) (a) Zhao, D.; Shi, Z.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52,
12426. (b) Liu, B.; Song, C.; Sun, C.; Zhou, S.; Zhu, J. J. Am. Chem.
Soc. 2013, 135, 16625. (c) Wang, C.; Huang, Y. Org. Lett. 2013, 15,
5294. (d) Wang, C.; Sun, H.; Fang, Y.; Huang, Y. Angew. Chem., Int.
Ed. 2013, 52, 5795. (e) Wang, C.-M.; Huang, Y. Org. Lett. 2013, 15
(20), 5294. (f) Zhao, D.-B.; Shi, Z.-Z.; Glorius, F. Angew. Chem. 2013,
125, 12652. (g) Zheng, L.; Hua, R. Chem. - Eur. J. 2014, 20, 2352.
(h) Su, B.; Wei, J.-B.; Wu, W.-L.; Shi, Z.-J. ChemCatChem 2015, 7,
(19) (a) Liu, Y.; McWhorter, W. W. J. Am. Chem. Soc. 2003, 125,
4240. (b) Nakajima, R.; Ogino, T.; Yokoshima, S.; Fukuyama, T. J.
Am. Chem. Soc. 2010, 132, 1236.
(20) (a) Arzel, E.; Rocca, P.; Grellier, P.; Labaeïd, M.; Frappier, F.;
́
́
Gueritte, F.; Gaspard, C.; Marsais, F.; Godard, A.; Queguiner, G. J.
Med. Chem. 2001, 44, 949. (b) Kumar, A.; Sharma, S.; Archana; Bajaj,
K.; Sharma, S.; Panwar, H.; Singh, T.; Srivastava, V. K. Bioorg. Med.
Chem. 2003, 11, 5293.
(21) Jin, Y.; Kim, K.; Song, S.; Kim, J.; Kim, J.; Park, S. H.; Lee, K.;
Suh, H. Bull. Korean Chem. Soc. 2006, 27, 1043.
(22) Murray, M. M.; Kaszynski, P.; Kaisaki, D. A.; Chang, W.;
Dougherty, D. A. J. Am. Chem. Soc. 1994, 116, 8152.
(23) (a) Heilman, W. P.; Battershell, R. D.; Pyne, W. J.; Goble, P.
H.; Magee, T. A.; Matthews, R. J. J. Med. Chem. 1978, 21, 906.
(b) Tsutsumi, K.; Inoue, Y.; Shima, A.; Iwasaki, K.; Kawamura, M.;
Murase, T. J. Clin. Invest. 1993, 92, 411. (c) Ran, Y.; Pei, H.; Shao, M.;
Chen, L. Chem. Biol. Drug Des. 2016, 87, 290.
́
́
2986. (i) Lerchen, A.; Vasquez-Cespedes, S.; Glorius, F. Angew.
Chem., Int. Ed. 2016, 55, 3208. (j) Zhou, S.-G.; Wang, J.-H.; Zhang,
F.-F.; Song, C.; Zhu, J. Org. Lett. 2016, 18 (10), 2427.
(7) (a) Dateer, R. B.; Chang, S. J. Am. Chem. Soc. 2015, 137, 4908.
(b) Piou, T.; Rovis, T. Nature 2015, 527, 86. (c) Hu, Z.-Y.; Tong, X.-
F.; Liu, G.-X. Org. Lett. 2016, 18, 1702. (d) Wu, Q.; Yan, D.-Y.; Chen,
Y.; Wang, T.; Xiong, F.; Wei, W.; Lu, Y.; Sun, W.-Y.; Li, J.-J.; Zhao, J.
Nat. Commun. 2017, 8, 14227. (e) Wang, X.-M.; Gensch, T.; Lerchen,
A.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2017, 139, 6506.
(f) Ikemoto, H.; Tanaka, R.; Sakata, K.; Kanai, M.; Yoshino, T.;
Matsunaga, S. Angew. Chem., Int. Ed. 2017, 56, 7156. (g) Chen, S.-Y.;
Han, X.-L.; Wu, J.-Q.; Li, Q.-J.; Chen, Y.-Y.; Wang, H.-G. Angew.
Chem., Int. Ed. 2017, 56, 9939. (h) Lopes, A. B.; Choury, M.; Wagner,
P.; Gulea, M. Org. Lett. 2019, 21 (15), 5943.
(8) Zhang, X.; Qi, Z.; Li, X. Angew. Chem., Int. Ed. 2014, 53, 10794.
(9) Zhou, X.-R.; Fan, Z.-L.; Zhang, Z.-Y.; Lu, P.; Wang, Y.-G. Org.
Lett. 2016, 18, 4706.
D
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