Organic Letters
Letter
(14) (a) Zhang, J.; Khaskin, E.; Anderson, N. P.; Zavalij, P. Y.;
Vedernikov, A. N. Chem. Commun. 2008, 3625−3627. (b) Liu, H.; Shi,
G.; Pan, S.; Jiang, Y.; Zhang, Y. Org. Lett. 2013, 15, 4098−4101.
(15) (a) Levina, A.; Muzart, J. Tetrahedron: Asymmetry 1995, 6, 147−
156. (b) Fache, F.; Piva, O. Tetrahedron: Asymmetry 2003, 14, 139−
143. (c) Le Bras, J.; Muzart, J. Tetrahedron: Asymmetry 2003, 14,
1911−1915. (d) García-Cabeza, A. L.; Marín-Barrios, R.; Moreno-
Dorado, F. J.; Ortega, M. J.; Massanet, G. M.; Guerra, F. M. Org. Lett.
2014, 16, 1598−1601. (e) Tran, B. L.; Driess, M.; Hartwig, J. F. J. Am.
Chem. Soc. 2014, 136, 17292−17301.
AUTHOR INFORMATION
■
Corresponding Author
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
(16) (a) Khan, K. M.; Maharvi, G. M.; Hayat, S.; Zia-Ullah; Iqbal
Choudhary, M.; Atta-ur-Rahman. Tetrahedron 2003, 59, 5549−5554.
(b) Feng, J.; Liang, S.; Chen, S.-Y.; Zhang, J.; Fu, S.-S.; Yu, X.-Q. Adv.
Synth. Catal. 2012, 354, 1287−1292. (c) Shi, E.; Shao, Y.; Chen, S.;
Hu, H.; Liu, Z.; Zhang, J.; Wan, X. Org. Lett. 2012, 14, 3384−3387.
(d) Guntreddi, T.; Vanjari, R.; Singh, K. N. Tetrahedron 2014, 70,
3887−3892. (e) Shimojo, H.; Moriyama, K.; Togo, H. Synthesis 2015,
47, 1280−1290.
We are grateful to the National Natural Science Foundation of
China (Grant Nos. 21472134 and 21172164), the Key
Laboratory of Organic Chemistry of Jiangsu Province, and
the Priority Academic Program Development of Jiangsu Higher
Education Institutions (PAPD) for financial support.
REFERENCES
■
(17) (a) Vindigni, V.; Cortivo, R.; Iacobellis, L.; Abatangelo, G.;
Zavan, B. Int. J. Mol. Sci. 2009, 10, 2972−2985. (b) Aliboni, A.;
D’Andrea, A.; Massanisso, P. J. Agric. Food Chem. 2011, 59, 282−288.
(1) See a recent review: Bauer, I.; Knolker, H.-J. Chem. Rev. 2015,
115, 3170−3387.
̈
(2) (a) Sun, C.-L.; Li, B.-J; Shi, Z.-J. Chem. Rev. 2011, 111, 1293−
1314. (b) Jia, F.; Li, Z. Org. Chem. Front. 2014, 1, 194−214. (c) Liu,
C.; Liu, D.; Lei, A. Acc. Chem. Res. 2014, 47, 3459−3470.
(3) (a) Qin, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 15893−15895.
(b) Paradine, S. M.; White, M. C. J. Am. Chem. Soc. 2012, 134, 2036−
2039. (c) Sekine, M.; Ilies, L.; Nakamura, E. Org. Lett. 2013, 15, 714−
717. (d) Hennessy, E. T.; Liu, R. Y.; Iovan, D. A.; Duncan, R. A.;
Betley, T. A. Chem. Sci. 2014, 5, 1526−1532.
́
(18) For a recent review, see: Isidro-Llobet, A.; Alvarez, M.;
Albericio, F. Chem. Rev. 2009, 109, 2455−2504.
(19) He, Y.; Mao, J.; Rong, G.; Yan, H.; Zhang, G. Adv. Synth. Catal.
2015, 357, 2125−2131.
(20) (a) Gao, H.-H.; Yan, C.-H.; Tao, X.-P.; Xia, Y.; Sun, H.-M.;
Shen, Q.; Zhang, Y. Organometallics 2010, 29, 4189−4192. (b) Yan,
C.; Wang, L.; Gao, H.; Sun, H.; Shen, Q. Chin. Sci. Bull. 2012, 57,
1953−1958. (c) Deng, H.-N.; Xing, Y.-L.; Xia, C.-L.; Sun, H.-M.;
Shen, Q.; Zhang, Y. Dalton Trans. 2012, 41, 11597−11607. (d) Xia, Y.;
Yan, C.; Li, Z.; Gao, H.; Sun, H.; Shen, Q.; Zhang, Y. Chin. Sci. Bull.
2013, 58, 493−499. (e) Xia, C.-L.; Xie, C.-F.; Wu, Y.-F.; Sun, H.-M.;
Shen, Q.; Zhang, Y. Org. Biomol. Chem. 2013, 11, 8135−8144.
(f) Wang, L.; Lu, B.; Zhu, A.; Sun, H.; Shen, Q. Chin. Sci. Bull. 2013,
58, 3624−3629. (g) Li, Z.; Liu, L.; Sun, H.-M.; Shen, Q.; Zhang, Y.
Dalton Trans. 2016, 45, 17739−17747.
(4) For selected examples, see: (a) Li, Z.; Yu, R.; Li, H. Angew. Chem.,
Int. Ed. 2008, 47, 7497−7500. (b) Volla, C. M. R.; Vogel, P. Org. Lett.
2009, 11, 1701−1704. (c) Han, W.; Ofial, A. R. Chem. Commun. 2009,
6023−6025. (d) Pan, S.; Liu, J.; Li, H.; Wang, Z.; Guo, X.; Li, Z. Org.
Lett. 2010, 12, 1932−1935. (e) Liu, P.; Zhou, C.-Y.; Xiang, S.; Che, C.-
M. Chem. Commun. 2010, 46, 2739−2741. (f) Ratnikov, M. O.; Xu, X.;
Doyle, M. P. J. Am. Chem. Soc. 2013, 135, 9475−9479. (g) Wei, W.-T.;
Zhou, M.-B.; Fan, J.-H.; Liu, W.; Song, R.-J.; Liu, Y.; Hu, M.; Xie, P.;
Li, J.-H. Angew. Chem., Int. Ed. 2013, 52, 3638−3641. (h) Zhao, J.;
Fang, H.; Zhou, W.; Han, J.; Pan, Y. J. Org. Chem. 2014, 79, 3847−
3855.
(5) (a) Li, C.-J.; Li, Z. Pure Appl. Chem. 2006, 78, 935−945. (b) Li,
Z.; Bohle, D. S.; Li, C.-J. Proc. Natl. Acad. Sci. U. S. A. 2006, 103,
8928−8933. (c) Li, C.-J. Acc. Chem. Res. 2009, 42, 335−344.
(d) Scheuermann, C. J. Chem. - Asian J. 2010, 5, 436−451.
(e) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215−1292.
(f) Girard, S. A.; Knauber, T.; Li, C.-J. Angew. Chem., Int. Ed. 2014, 53,
74−100.
(6) (a) Li, Z.; Cao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2007, 46,
6505−6507. (b) Pan, S.; Liu, J.; Li, Y.; Li, Z. Chin. Sci. Bull. 2012, 57,
2382−2386.
(7) Wang, Z.; Zhang, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Org. Lett. 2008,
10, 1863−1866.
(8) (a) Li, Y.-Z.; Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. Angew. Chem.,
Int. Ed. 2009, 48, 3817−3820. (b) Song, C.-X.; Cai, G.-X.; Farrell, T.
R.; Jiang, Z.-P.; Li, H.; Gan, L.-B.; Shi, Z.-J. Chem. Commun. 2009,
6002−6004. (c) Shi, J.-L.; Zhang, J.-C.; Wang, B.-Q.; Hu, P.; Zhao, K.-
Q.; Shi, Z.-J. Org. Lett. 2016, 18, 1238−1241.
(21) For recent examples, see: (a) He, J.; Wasa, M.; Chan, K. S. L.;
Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 3387−3390. (b) Ye, S.; Yang,
W.; Coon, T.; Fanning, D.; Neubert, T.; Stamos, D.; Yu, J.-Q. Chem. -
Eur. J. 2016, 22, 4748−4752. (c) Bai, D.-C.; Yu, F.-L.; Wang, W.-Y.;
Chen, D.; Li, H.; Liu, Q.-R.; Ding, C.-H.; Chen, B.; Hou, X.-L. Nat.
Commun. 2016, 7, 11806−11816.
(22) For examples of iron-based catalytic systems involving other
imidazolinium salts, see: (a) Hatakeyama, T.; Hashimoto, S.; Ishizuka,
K.; Nakamura, M. J. Am. Chem. Soc. 2009, 131, 11949−11963.
(b) Rosa, J. N.; Reddy, R. S.; Candeias, N. R.; Cal, P. M. S. D.; Gois, P.
M. P. Org. Lett. 2010, 12, 2686−2689. (c) Chua, Y.-Y.; Duong, H. A.
Chem. Commun. 2016, 52, 1466−1469 and references cited therein.
(23) Wang, J.; Liu, C.; Yuan, J.; Lei, A. Chem. Commun. 2014, 50,
4736−4739.
(24) Wang, C.-Y.; Song, R.-J.; Wei, W.-T.; Fan, J.-H.; Li, J.-H. Chem.
Commun. 2015, 51, 2361−2363.
(25) Majji, G.; Rout, S. K.; Rajamanickam, S.; Guin, S.; Patel, B. K.
Org. Biomol. Chem. 2016, 14, 8178−8211.
(26) For more examples using ethylbenzene as a coupling partner,
(27) (a) Neuse, E. W.; Meirim, M. G. Transition Met. Chem. 1984, 9,
(9) Xia, Q.; Chen, W.; Qiu, H. J. Org. Chem. 2011, 76, 7577−7582.
(10) Cheng, Y.; Dong, W.; Wang, L.; Parthasarathy, K.; Bolm, C. Org.
Lett. 2014, 16, 2000−2002.
(11) (a) Liu, X.; Chen, Y.; Li, K.; Wang, D.; Chen, B. Chin. J. Chem.
2012, 30, 2285−2291. (b) Guo, S.; Li, Y.; Wang, Y.; Guo, X.; Meng,
X.; Chen, B. Adv. Synth. Catal. 2015, 357, 950−954.
205−208. (b) Marlin, D. S.; Olmstead, M. M.; Mascharak, P. K. Inorg.
Chem. 2003, 42, 1681−1687. (c) Demir, S.; Gokcȩ , Y.; Roisnel, T.;
̈
̈
̇
Sortais, J.-B.; Darcel, C.; Ozdemir, I. C. R. Chim. 2014, 17, 541−548.
(12) (a) Wang, T.; Yuan, L.; Zhao, Z.; Shao, A.; Gao, M.; Huang, Y.;
Xiong, F.; Zhang, H.; Zhao, J. Green Chem. 2015, 17, 2741−2744.
(b) Zhao, Z.; Wang, T.; Yuan, L.; Hu, X.; Xiong, F.; Zhao, J. Adv.
Synth. Catal. 2015, 357, 2566−2570.
(13) (a) Guo, L.-N.; Wang, S.; Duan, X.-H.; Zhou, S.-L. Chem.
Commun. 2015, 51, 4803−4806. (b) Yang, K.; Song, Q. Org. Lett.
2015, 17, 548−551.
D
Org. Lett. XXXX, XXX, XXX−XXX