Organic Letters
Letter
Huang, D. L.; Aguila, M. J. B.; Schmidt, G.; Shahu, A.; Warren, T. H.
Angew. Chem., Int. Ed. 2012, 51, 6488.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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(6) (a) Zhang, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 28. (b) Deshidi,
R.; Kumar, M.; Devari, S.; Shah, B. A. Chem. Commun. 2014, 50, 9533.
(7) Zhang, C.; Xu, Z.-J.; Zhang, L.-J.; Jiao, N. Angew. Chem., Int. Ed.
2011, 50, 11088. (b) Zhang, C.; Zong, X.-L.; Zhang, L.-G.; Jiao, N. Org.
Lett. 2012, 14, 3280.
Experimental procedures, product characterizations,
crystallographic data, and copies of the 1H and 13C
(8) Zhang, Z. L.; Su, J. H.; Zha, Z. G.; Wang, Z. Y. Chem. Commun.
2013, 49, 8982.
Crystallographic data for 3ja (CIF)
(9) Wu, X.; Gao, Q. H.; Liu, S.; Wu, A. X. Org. Lett. 2014, 16, 2888.
(10) (a) Chu, L.; Xiao, K. J.; Yu, J. Q. Science 2014, 346, 451. (b) Wang,
X. C.; Hu, Y.; Bonacorsi, S.; Hong, Y.; Burrell, R.; Yu, J. Q. J. Am. Chem.
Soc. 2013, 135, 10326. (c) Mei, T. S.; Giri, R.; Maugel, N.; Yu, J. Q.
Angew. Chem., Int. Ed. 2008, 47, 5215. (d) Dudnik, A. S.; Chernyak, N.;
Huang, C. H.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 8729.
(11) For representative reviews on this topic, see: (a) Nicolaou, K. C.;
Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442.
(b) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem.
Rev. 2002, 102, 1359 and references therein. (c) Littke, A. F.; Fu, G. C.
AUTHOR INFORMATION
Corresponding Authors
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Notes
The authors declare no competing financial interest.
Angew. Chem., Int. Ed. 2002, 41, 4176. (d) Sturmer, R. Angew. Chem., Int.
̈
Ed. 1999, 38, 3307 and references therein. (e) Spielvogel, D. J.;
Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 3500. (f) Littke, A. F.; Fu, G.
C. Angew. Chem., Int. Ed. 1998, 37, 3387. (g) Choudary, B. M.; Sridhar,
C.; Kantam, M. L.; Venkanna, G. T.; Sreedhar, B. J. Am. Chem. Soc. 2005,
127, 9948. (h) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J.
Am. Chem. Soc. 2001, 123, 12411. (i) Pelletier, J. C.; Youssefyeh, R. D.;
Campbell, H. F. U.S. Patent 4920219, 1990.
(12) In the presence of additional HCl or HBr under standard
conditions, hydrated hemiacetal 1ab could react with 2-iodoaniline 2aa
and afford the oxidative coupling product 3aa in 59 and 61% yield,
respectively.
(13) (a) Xue, W. J.; Li, Q.; Zhu, Y. P.; Wang, J. G.; Wu, A. X. Chem.
Commun. 2012, 48, 3485. (b) Togo, H.; Iida, S. Synlett 2006, 2006, 2159.
(c) Gao, Q. H.; Wu, X.; Liu, S.; Wu, A. X. Org. Lett. 2014, 16, 1732.
(14) (a) Wu, X. F.; Natte, K. Adv. Synth. Catal. 2016, 358, 336. (b) Wu,
X. F.; Gong, J. L.; Qi, X. X. Org. Biomol. Chem. 2014, 12, 5807.
ACKNOWLEDGMENTS
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This work was supported by the National Natural Science
Foundation of China (Grant Nos. 21272085 and 21472056). We
also thank Dr. Chuanqi Zhou, Hebei University, for analytical
support. We also acknowledge an excellent doctorial dissertation
cultivation grant from Central China Normal University
(2015YBYB087).
REFERENCES
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(1) (a) Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th ed.; Blackwell
Science: Oxford, U.K., 2000; Chapter 25. (b) Katritzky, A. R.
Comprehensive Heterocyclic Chemistry III; Elsevier: Oxford, U.K., 2008;
Vol. 11.
(2) For representative reviews on this topic, see: (a) Yu, Z. Z.; Ma, B.;
Chen, M. J.; Wu, H. H.; Liu, L.; Zhang, J. L. J. Am. Chem. Soc. 2014, 136,
6904. (b) Jia, S. K.; Xing, D.; Zhang, D.; Hu, W. H. Angew. Chem., Int. Ed.
2014, 53, 13098. (c) Tang, C. H.; Jiao, N. J. Am. Chem. Soc. 2012, 134,
18924. (d) Li, W.; Duan, Z. L.; Jiang, R.; Lei, A. W. Org. Lett. 2015, 17,
1397. (e) Anderson, L. L.; Arnold, J.; Bergman, R. G. J. Am. Chem. Soc.
2005, 127, 14542. (f) Jagadeesh, R. V.; Surkus, A. E.; Junge, H.; Pohl, M.
M.; Radnik, J.; Rabeah, J.; Huan, H. M.; Schunemann, V.; Bruckner, A.;
̈
̈
Beller, M. Science 2013, 342, 1073. (g) Xu, C.; Jia, F. C.; Cai, Q.; Li, D.
K.; Zhou, Z. W.; Wu, A. X. Chem. Commun. 2015, 51, 6629.
(3) For representative references, see: (a) Dyker, G. Handbook of C−H
Transformations Applications in Organic Synthesis; Wiley-VCH:
Weinheim, 2005. (b) Metal Catalyzed Cross-Coupling Reactions, 2nd
ed.; De Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
(c) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J.,
Eds.; Wiley-VCH: New York, 1998. (d) Comprehensive Organic
Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford,
U.K., 1991; Vol. 7.
(4) (a) Li, C.-J. Acc. Chem. Res. 2009, 42, 335. (b) Chen, X.; Engle, K.
M.; Wang, D. H.; Yu, J. Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
(c) Ashenhurst, J. A. Chem. Soc. Rev. 2010, 39, 540. (d) Boorman, T. C.;
Larrosa, I. Chem. Soc. Rev. 2011, 40, 1910. (e) You, S. l.; Xia, J.-B. Top.
Curr. Chem. 2009, 292, 165. (f) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S.
Chem. Soc. Rev. 2011, 40, 5068. (g) Liu, C.; Zhang, H.; Shi, W.; Lei, A. W.
Chem. Rev. 2011, 111, 1780. (h) Yeung, C. S.; Dong, V. M. Chem. Rev.
2011, 111, 1215. (i) Sun, C. L.; Shi, Z. J. Chem. Rev. 2014, 114, 9219.
(j) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed.
2012, 51, 8960. (k) Le Bras, J.; Muzart, J. Chem. Rev. 2011, 111, 1170.
(l) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293. (m) Liu, C.;
Yuan, J. W.; Gao, M.; Tang, S.; Li, W.; Shi, R. Y.; Lei, A. W. Chem. Rev.
2015, 115, 12138.
(5) (a) Neumann, J. J.; Rakshit, S.; Droge, T.; Glorius, F. Angew. Chem.,
Int. Ed. 2009, 48, 6892. (b) Pan, J.; Su, M. J.; Buchwald, S. L. Angew.
Chem., Int. Ed. 2011, 50, 8647. (c) Zhang, X. S.; Wang, M.; Li, P. H.;
Wang, L. Chem. Commun. 2014, 50, 8006. (d) Gephart, R. T., III;
D
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