Journal of the American Chemical Society
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Org. Lett. 2012, 14, 4525. (e) Liu, C.; Zhang, W.; Dai, L.-X.; You, S.-L.
Chem. Asian J. 2014, 9, 2113.
ASSOCIATED CONTENT
Supporting Information
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(5) For recent reviews, see: (a) Campeau, L. C.; Fagnou, F. Chem.
Commun. 2006, 1253. (b) Alberico, D.; Scott, M. E.; Lautens, M.
Chem. Rev. 2007, 107, 174. (c) Chen, X.; Engle, K. M.; Wang, D.; Yu, J.
Angew. Chem., Int. Ed. 2009, 48, 5094. (d) Ackemann, L.; Vicente, R.;
Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792. (e) Rossi, R.;
Bellina, F.; Lessi, M.; Manzini, C. Adv. Synth. Catal. 2014, 356, 17.
(6) (a) Maeda, K.; Farrington, E. J.; Galardon, E.; John, B. D.;
Brown, J. M. Adv. Synth. Catal. 2002, 344, 104. (b) Glover, B.; Harvey,
A. K.; Liu, B.; Sharp, J. M.; Tymoschenko, M. F. Org. Lett. 2003, 5, 301.
(c) Lautens, M.; Fang, Y. Q. Org. Lett. 2003, 5, 3679. (d) Wang, J.-X.;
McCubbin, J. A.; Jin, M.; Laufer, R. S.; Mao, Y.; Crew, A. P.; Mulvihill,
M. J.; Snieckus, V. Org. Lett. 2008, 10, 2923. (e) Ueda, K.; Yanagisawa,
S.; Yamaguchi, J.; Itami, K. Angew. Chem., Int. Ed. 2010, 49, 8946.
(f)Tang, S.-Y.; Guo, Q.-X.; Fu, Y. Chem. Eur. J. 2011, 17, 13866.
(7) Reviews for reductive Heck reaction, see: (a) Oestreich, M., Ed.
The Mizoroki-Heck Reaction; Wiley: Chichester, 2009. (b) Limk, J. T.;
Overman, L. E. Metal-catalyzed Cross Coupling reaction; Diederick,
F., Stang, P. J., Eds.; Wiely-VCH: Weinheim, 1998. (c) Brase, S.; de
Meijere, A. Cross-Coupling of Organyl Halides with Alkenes-The Heck
Reaction. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere,
A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004. (d)
Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. Se-
lected examples for asymmetric reductive Heck reaction: (e) Namys-
lo, J. C.; Kaufmann, D. E. Chem. Ber. 1997, 130, 1327. (f) Wu, X.-Y.; Wu,
H.-D.; Zhou, Q.-L.; Chan, A. S. C. Tetrahedron: Asymmetry 2000, 11,
1255. (g) Minatti, A.; Zheng, X.; Buchwald, S. L. J. Org. Chem. 2007, 72,
9253.
(8) Zhao, L.; Li, Z.-Y.; Chang, L.; Xu, J.-Y.; Yao, H.-Q.; Wu X.-M.
Org. Lett. 2012, 14, 2066.
(9) Brown, D.; Grigg, R.; Sridharan, V.; Tambyrajah, V.
Tetrahedron Lett. 1995, 36, 8137.
(10) For recent reviews on quaternary stereocenters: (a) Christof-
fers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591. (b) Denissova,
I.; Barriault, L. Tetrahedron 2003, 10105. (c) Christoffers, J.; Baro, A.
Adv. Synth. Catal. 2005, 347, 1473. (d) Bella, M.; Gasperi, T. Synthesis
2009, 1583. (e) Quasdorf, K. W.; Overman, L. E. Nature 2014, 516,
7530.
(11) Tan, C.-J.; Di, Y.-T.; Wang, Y.-H.; Zhang, Y.; Si, Y.-K.; Zhang,
Q.; Gao, S.; Hu, X.-J.; Fang, X.; Li, S.-F.; Hao, X.-J. Org. Lett. 2010, 12,
2370.
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Full experimental and characterization data, including H
and 13C NMR for all the new compounds, chiral HPLC spectra
for the products, and crystal data are available free of charge
AUTHOR INFORMATION
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENT
We are grateful for the financial support from the National
Natural Science Foundation of P. R. China (21372202), the
New Century Excellent Talents in University (NCET-12-1086),
and the Zhejiang Natural Science Fund for Distinguished
Young Scholars (R14B020005).
REFERENCES
(1) For selected reviews, see: (a) Pape, A. R.; Kaliappan, K. P.; Kün-
dig, E. P. Chem. Rev. 2000, 100, 2917. (b) Harman, W. D. Top. Organ-
omet. Chem. 2004, 7, 95. (c) Lopez Ortiz, F.; Iglesias, M. J.; Fernan-
dez, I.; Andujar Sanchez, C. M.; Gomez, G. R. Chem. Rev. 2007, 107,
1580. (d) Pouysegu, L.; Deffieux, D.; Quideau, S. Tetrahedron 2010,
66, 2235. (e) Roche, S. P.; Porco, Jr., J. A. Angew. Chem., Int. Ed. 2011,
50, 4068. (f) Zhuo, C.-X.; Zhang, W.; You, S.-L. Angew. Chem., Int. Ed.
2012, 51, 12662. (g) Ding, Q.; Ye, Y.; Fan, R. Synthesis. 2013, 1. (h)
Roche, S. P.; Tendoung, J. Y.; Treguier, B. Tetrahedron 2014, DOI:
10.1016/j.tet.2014.06.054.
(2) For a review, see: Wang, D. S.; Chen, Q.-A.; Lu, S.-M.; Zhou,
Y.-G. Chem. Rev. 2012, 112, 2557.
(3) For Pd-catalyzed arylative dearomatization reactions: (a) Gar-
cía-Fortanet, J.; Kessler, F.; Buchwald, S. L. J. Am. Chem. Soc. 2009,
131, 6676. (b) Bedford, R. B.; Butts, C. P.; Haddow, M. F.; Osborne, R.;
Sankey, R. F. Chem. Commun. 2009, 45, 4832. (c) Bedford, R. B.; Fey,
N.; Haddow, M. F.; Sankey, R. F. Chem. Commun. 2011, 47, 3649. (d)
Rousseaux, S.; García-Fortanet, J.; Del Aguila Sanchez, M. A.; Buch-
wald, S. L. J. Am. Chem. Soc. 2011, 133, 9282. (e) Wu, K.-J.; Dai, L.-X.;
You, S,-L. Org. Lett. 2012, 14, 3772. (f) Wu, K.-J.; Dai, L.-X.; You, S.-L.
Chem. Commun. 2013, 49, 8620. (g) Xu, R.-Q.; Gu, Q.; Wu, W.-T.;
Zhao, Z.-A.; You, S.-L. J. Am. Chem. Soc. 2014, 136, 15469. (h) Du, K.;
Guo, P.; Chen, Y.; Cao, Z.; Wang, Z.; Tang, W.-J. Angew. Chem., Int.
Ed. 2015, 54, 3033.
(4) For Cu-catalyzed arylative dearomatization of indoles with ar-
yliodoniums: (a) Zhu, S.; MacMillan, D. W. C. J. Am. Chem. Soc. 2012,
134, 10815. (b) Guo, F.; Wang, L.; Wang, P.; Yu, J.; Han, J. Asian J. Org.
Chem. 2012, 1, 218. (c) Kieffer, M. E.; Chuang, K. V.; Reisman, S. E.
Chem. Sci. 2012, 3, 3170. d) Liu, C.; Zhang, W.; Dai, L.-X.; You, S.-L.
(12) Liu, J.-F.; Jiang, Z.-Y.; Wang, R.-R.; Zheng, Y.-T.; Chen, J.-J.;
Zhang, X.-M.; Ma, Y.-B. Org. Lett. 2007, 9, 4127.
(13) Blackman, A. J.; Hambley, T. W.; Picker, K.; Taylor, W. C.;
Thirasasana, N. Tetrahedron Lett. 1987, 28, 5561.
(14) No C7-arylation product was detected during optimization of
the reaction conditions.
(15) The following substrates were failed to give the desired prod-
ucts under the optimal reaction conditions. 2,3-Diphenylindole-1H-
indole was observed as the major byproduct for the former, while
hydrodebromination reaction occurred for the latter.
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