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ChemComm
Page 4 of 4
COMMUNICATION
Journal Name
X. Liang, R.-R. Liu and Y.-X. Jia, J. Am.DCOhIe: m10..1S0o39Vci/.e,Cw29AC0rtC1ic80le3,O516n4l6in0De,
13945.
(a) C. Shen, R.-R. Liu, R.-J. Fan, Y.-L. Li, T.-F. Xu, J.-R. Gao and
Y.-X. Jia, J. Am. Chem. Soc., 2015, 137, 4936; (b) F. Wei, L.
Wei, L. Zhou, C.-H. Tung, Y. Ma and Z. Xu, Asian J. Org. Chem.,
2016, 5, 971; (c) R.-R. Liu, Y. Xu, R.-X. Liang, B. Xiang, H.-J.
Xie, J.-R. Gao and Y.-X. Jia, Org. Biomol. Chem., 2017, 15,
2711.
intermediate I, which undergoes an intermolecular
carbopalladation with alkyne followed by ligand exchange to
generate intermediate II. A subsequent reductive elimination
affords indole III. The intramolecular dearomative Heck
reaction is then occurred to give the final product indoline 3a
through oxidative addition, migratory insertion of Ar-Pd to
indole, and β-hydride elimination.
In summary, we have developed a palladium-catalyzed
domino Larock annulation/dearomative Heck reaction of N-
bromobenzoyl o-iodoaniline with alkynes. The reaction
provides an efficient and straightforward access to tetracyclic
indoline derivatives, which are achieved in moderate to
excellent yields with a broad substrate scope. Two new rings
and three chemical bonds are formed in a single step in this
domino sequence.
6
7
(a) D. A. Petrone, A. Yen, N. Zeidan and M. Lautens, Org. Lett.,
2015, 17, 4838; (b) S. Chen, X.-X. Wu, J. Wang, X.-H. Hao, Y.
Xia, Y. Shen, H. Jing and Y.-M. Liang, Org. Lett., 2016, 18,
4016; (c) R.-R. Liu, T.-F. Xu, Y.-G. Wang, B. Xiang, J.-R. Gao
and Y.-X. Jia, Chem. Commun., 2016, 52, 13664; (d) D. A.
Petrone, M. Kondo, N. Zeidan and M. Lautens, Chem. Eur. J.,
2016, 22, 5684; (e) R.-R. Liu, Y.-G. Wang, Y.-L. Li, B.-B. Huang,
R.-X. Liang and Y.-X. Jia, Angew. Chem. Int. Ed., 2017, 56,
7475; (f) Y.-G. Wang, R.-R. Liu, J.-R. Gao and Y.-X. Jia, Chin. J.
Org. Chem., 2017, 37, 691; (g) N. Zeidan, T. Beisel, R. Ross
and M. Lautens, Org. Lett., 2018, 20, 7332; (h) C. Shen, N.
Zeidan, Q. Wu, C. B. J. Breuers, R.-R. Liu, Y.-X. Jia and M.
Lautens, Chem. Sci., 2019, 10, 3118. (i) J.-Q. Weng, L.-L. Xing,
W.-R. Hou, R.-X. Liang and Y.-X. Jia, Org. Chem. Front., 2019,
6, 1577. (j) R.-X. Liang, K. Wang, Q. Wu, W.-J. Sheng and Y.-X.
Jia, Organometallics, 2019, DOI: 10.1021/acs.organomet.
9b00112.
For dearomative Heck arylation of furans and pyrroles: (a) J.
Liu, H. Peng, L. Lu, X. Xu, H. Jiang and B. Yin, Org. Lett., 2016,
18, 6440; (b) J. Liu, X. Xu, J. Li, B. Liu, H. Jiang and B. Yin,
Chem. Commun., 2016, 52, 9550; (c) J. Liu, H. Peng, Y. Yang,
H. Jiang and B. Yin, J. Org. Chem., 2016, 81, 9695; (d) X. Xu, J.
Liu, L. Lu, F. Wang and B. Yin, Chem. Commun., 2017, 53,
7796; (e) P. Yang and S.-L. You, Org. Lett., 2018, 20, 7684.
R. C. Larock and E. K. J. Yum, Am. Chem. Soc., 1991, 113,
6689.
We are grateful for the financial support from the National
Natural Science Foundation of China (21702184 and
21772175).
Conflicts of interest
The authors declare no conflict of interest.
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Notes and references
1
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Selected
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arylative
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5
(a) L. Zhao, Z. Li, L. Chang, J. Xu, H. Yao and X. Wu, Org. Lett.,
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4 | J. Name., 2012, 00, 1-3
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