Organic Letters
ization of new compounds NMR spectra of new
Letter
(6) Ouyang, X.-H.; Song, R.-J.; Wang, C.-Y.; Yang, Y.; Li, J.-H.
Chem. Commun. 2015, 51, 14497−14500.
(7) Wang, S.; Guo, L. N.; Wang, H.; Duan, X.-H. Org. Lett. 2015, 17,
4798−4801.
(8) Jia, K.; Pan, Y.; Chen, Y. Angew. Chem., Int. Ed. 2017, 56, 2478−
AUTHOR INFORMATION
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2481.
Corresponding Author
ORCID
(9) For some examples, see: (a) Ochiai, M.; Masaki, Y.; Shiro, M. J.
Org. Chem. 1991, 56, 5511−5513. (b) Zhdankin, V. V.; Kuehl, C. J.;
Krasutsky, A. P.; Bolz, J. T.; Simonsen, A. J. J. Org. Chem. 1996, 61,
6547−6551. (c) Brand, J. P.; Charpentier, J.; Waser, J. Angew. Chem.,
Int. Ed. 2009, 48, 9346−9349. (d) Liu, X.; Wang, Z.; Cheng, X.; Li, C.
J. J. Am. Chem. Soc. 2012, 134, 14330−14333. (e) Collins, K. D.; Lied,
F.; Glorius, F. Chem. Commun. 2014, 50, 4459−4461. (f) Feng, C.;
Loh, T.-P. Angew. Chem., Int. Ed. 2014, 53, 2722−2726. (g) Xie, F.;
Qi, Z.; Yu, S.; Li, X. J. J. Am. Chem. Soc. 2014, 136, 4780−4787.
(h) Zhang, R.-Y.; Xi, L.-Y.; Zhang, L.; Liang, S.; Chen, S.-Y.; Yu, X.-Q.
RSC Adv. 2014, 4, 54349−54353. (i) Chen, C. C.; Waser, J. Org. Lett.
2015, 17, 736−739. (j) Chen, F.; Hashmi, A. S. K. Org. Lett. 2016, 18,
2880−2882. For reviews, see: (k) Zhdankin, V. V.; Stang, P. J.
Tetrahedron 1998, 54, 10927−10966. (l) Brand, J. P.; Waser, J. Chem.
Soc. Rev. 2012, 41, 4165−4179.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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This work was supported by the National Science Foundation
of China (Nos. 21572099 and 21332005) and the Natural
Science Foundation of Jiangsu Province (No. BK20151379).
This study was supported by the Open Project of State Key
Laboratory Cultivation Base for TCM Quality and Efficacy,
Nanjing University of Chinese Medicine (Nos. TCMQ and E
201702). R.L. and J.D. appreciate the open training program of
the undergraduate organic experiment course (0205145031-6)
.
(10) (a) Li, G.; Chen, R.; Wu, L.; Fu, Q.; Zhang, X.; Tang, Z. Angew.
Chem., Int. Ed. 2013, 52, 8432−8436. (b) Li, G.; Wu, L.; Lv, G.; Liu,
H.; Fu, Q.; Zhang, X.; Tang, Z. Chem. Commun. 2014, 50, 6246−
6248.
(11) Nakajima, K.; Nojima, S.; Sakata, K.; Nishibayashi, Y.
ChemCatChem 2016, 8, 1028−1032.
(12) v. Meyer, E. J. Prakt. Chem. (Leipzig) 1908, 78, 497−534.
(13) Chen, W.; Liu, Z.; Tian, J.; Li, J.; Ma, J.; Cheng, X.; Li, G. J. Am.
Chem. Soc. 2016, 138, 12312−12315.
REFERENCES
■
(14) (a) Nakajima, K.; Nojima, S.; Nishibayashi, Y. Angew. Chem.,
(1) (a) Lu, G.; Li, Y.-M.; Li, X.-S.; Chan, A. S. C. Coord. Chem. Rev.
2005, 249, 1736−1744. (b) Bauer, T. Coord. Chem. Rev. 2015, 299,
83−150.
́
́
Int. Ed. 2016, 55, 14106−14110. (b) Gutierrez-Bonet, A.; Tellis, J. C.;
Matsui, J. K.; Vara, B. A.; Molander, G. A. ACS Catal. 2016, 6, 8004−
8008.
(2) (a) Brand, J. P.; Waser, J. Chem. Soc. Rev. 2012, 41, 4165−4179.
(b) Aubineau, T.; Cossy, J. Chem. Commun. 2013, 49, 3303−3305.
(15) Buzzetti, L.; Prieto, A.; Roy, S. R.; Melchiorre, P. Angew. Chem.,
Int. Ed. 2017, 56, 15039−15043.
́
́
̀
(c) Fernandez Gonzalez, D.; Brand, J. P.; Mondiere, R.; Waser, J. Adv.
Synth. Catal. 2013, 355, 1631−1639. (d) Finkbeiner, P.;
Weckenmann, N. M.; Nachtsheim, B. J. Org. Lett. 2014, 16, 1326−
1329. (e) Frei, R.; Wodrich, M. D.; Hari, D. P.; Borin, P.-A.;
Chauvier, C.; Waser, J. J. Am. Chem. Soc. 2014, 136, 16563−16573.
(3) (a) Negishi, E.-i.; Anastasia, L. Chem. Rev. 2003, 103, 1979−
2018. (b) Nicolai, S.; Piemontesi, C.; Waser, J. Angew. Chem., Int. Ed.
2011, 50, 4680−4683. (c) Wang, Z.; Li, X.; Huang, Y. Angew. Chem.,
Int. Ed. 2013, 52, 14219−14223. (d) Xie, F.; Qi, Z.; Yu, S.; Li, X. J. J.
Am. Chem. Soc. 2014, 136, 4780−4787. (e) Ivanova, M. V.; Bayle, A.;
Besset, T.; Poisson, T.; Pannecoucke, X. Angew. Chem., Int. Ed. 2015,
54, 13406−13410. (f) Wu, J.; Yoshikai, N. Angew. Chem., Int. Ed.
2015, 54, 11107−11111. (g) Yang, X.-F.; Hu, X.-H.; Feng, C.; Loh,
T.-P. Chem. Commun. 2015, 51, 2532−2535. (h) Hari, D. P.; Waser, J.
J. J. Am. Chem. Soc. 2016, 138, 2190−2193. (i) Chen, Z. M.; Nervig,
C. S.; DeLuca, R. J.; Sigman, M. S. Angew. Chem., Int. Ed. 2017, 56,
6651−6654. (j) Hari, D. P.; Waser, J. J. Am. Chem. Soc. 2017, 139,
8420−8423. (k) Li, X.; Xie, X.; Sun, N.; Liu, Y. Angew. Chem., Int. Ed.
2017, 56, 6994−6998. (l) Shen, K.; Wang, Q. Chem. Sci. 2017, 8,
8265−8270. (m) Wang, S.-B.; Gu, Q.; You, S.-L. J. J. Org. Chem.
2017, 82, 11829−11835. (n) Han, W.-J.; Wang, Y.-R.; Zhang, J.-W.;
Chen, F.; Zhou, B.; Han, B. Org. Lett. 2018, 20, 2960−2963.
(4) (a) Liu, X.; Wang, Z.; Cheng, X.; Li, C. J. Am. Chem. Soc. 2012,
134, 14330−14333. (b) Le Vaillant, F.; Courant, T.; Waser, J. Angew.
Chem., Int. Ed. 2015, 54, 11200−11204. (c) Tan, H.; Li, H.; Ji, W.;
Wang, L. Angew. Chem., Int. Ed. 2015, 54, 8374−8377. (d) Zhou, Q.;
Guo, W.; Ding, W.; Wu, X.; Chen, X.; Lu, L.; Xiao, W. Angew. Chem.,
Int. Ed. 2015, 54, 11196−11199. (e) Wang, P.-F.; Feng, Y.-S.; Cheng,
Z.-F.; Wu, Q.-M.; Wang, G.-Y.; Liu, L.-L.; Dai, J.-J.; Xu, J.; Xu, H.-J. J.
Org. Chem. 2015, 80, 9314−9320. (f) Chen, F.; Hashmi, A. S. K. Org.
Lett. 2016, 18, 2880−2882.
(16) Gu, F.; Huang, W.; Liu, X.; Chen, W.; Cheng, X. Adv. Synth.
Catal. 2018, 360, 925−931.
(17) Zhang, H.-H.; Yu, S. J. Org. Chem. 2017, 82, 9995−10006.
́
́
(18) Gutierrez-Bonet, A.; Remeur, C.; Matsui, J. K.; Molander, G. A.
J. Am. Chem. Soc. 2017, 139, 12251−12258. For more details of
K2S2O8 and HE in this transformation, see the SI.
(19) Verrier, C.; Alandini, N.; Pezzetta, C.; Moliterno, M.; Buzzetti,
L.; Hepburn, H. B.; Vega-Pen
Catal. 2018, 8, 1062−1066.
̃
aloza, A.; Silvi, M.; Melchiorre, P. ACS
(20) Mo, H.; Bao, W. Tetrahedron 2011, 67, 4793−4799.
(21) Luo, C.-Z.; Gandeepan, P.; Wu, Y.-C.; Chen, W.-C.; Cheng, C.-
H. RSC Adv. 2015, 5, 106012−106018.
(22) Huang, W.; Chen, W.; Wang, G.; Li, J.; Cheng, X.; Li, G. ACS
Catal. 2016, 6, 7471−7474.
(5) (a) Huang, H.; Zhang, G.; Gong, L.; Zhang, S.; Chen, Y. J. J. Am.
Chem. Soc. 2014, 136, 2280−2283. (b) Huang, H.; Zhang, G.; Chen,
Y. Angew. Chem., Int. Ed. 2015, 54, 7872−7876.
D
Org. Lett. XXXX, XXX, XXX−XXX