Abstract

Methods that can directly arylate pyridines have significant potential in synthetic chemistry. Herein, we present palladium-catalyzed C–H arylation of pyridines with aryl triflates that occurs regioselectively at the C3 positions of the pyridine core. A variety of aryl triflates and pyridines were applicable to the reaction to provide C3-arylated pyridines regardless of sterics or electronics of the pyridine cores.

References

1)

R. D. Taylor, M. MacCoss, A. D. G. Lawson, J. Med. Chem. 2014, 57, 5845.

2) a)

J. Jin, D. W. C. MacMillan, Nature 2015, 525, 87.

b)

H. Nagae, Y. Shibata, H. Tsurugi, K. Mashima, J. Am. Chem. Soc. 2015, 137, 640.

c)

Y. Nakao, K. S. Kanyiva, T. Hiyama, J. Am. Chem. Soc. 2008, 130, 2448.

d)

B.-T. Guan, Z. Hou, J. Am. Chem. Soc. 2011, 133, 18086.

e)

M. Tobisu, I. Hyodo, N. Chatani, J. Am. Chem. Soc. 2009, 131, 12070.

f)

A. H. Berman, J. C. Lewis, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2008, 130, 14926.

g)

B. Liu, Y. Huang, J. Lan, F. Song, J. You, Chem. Sci. 2013, 4, 2163.

h)

I. B. Seiple, S. Su, R. A. Rodriguez, R. Gianatassio, Y. Fujiwara, A. L. Sobel, P. S. Baran, J. Am. Chem. Soc. 2010, 132, 13194.

i)

J. C. Lewis, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2007, 129, 5332.

3) a)

B.-J. Li, Z.-J. Shi, Chem. Sci. 2011, 2, 488.

b)

M. Ye, G.-L. Gao, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 6964.

4) a)

Y. Nakao, Y. Yamada, N. Kashihara, T. Hiyama, J. Am. Chem. Soc. 2010, 132, 13666.

b)

T. Andou, Y. Saga, H. Komai, S. Matsunaga, M. Kanai, Angew. Chem., Int. Ed. 2013, 52, 3213.

c)

S. Yamamoto, Y. Saga, T. Andou, S. Matsunaga, M. Kanai, Adv. Synth. Catal. 2014, 356, 401.

5) a)

T. Iwai, M. Sawamura, ACS Catal. 2015, 5, 5031.

b)

D. Stephens, O. V. Larionov, Tetrahedron 2015, 71, 8683.

c)

K. M. Engle, J.-Q. Yu, J. Org. Chem. 2013, 78, 8927.

d)

Y. Nakao, Synthesis 2011, 3209.

6)

M. Ye, G.-L. Gao, A. J. F. Edmunds, P. A. Worthington, J. A. Morris, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 19090.

7)

F. Dai, Q. Gui, J. Liu, Z. Yang, X. Chen, R. Guo, Z. Tan, Chem. Commun. 2013, 49, 4634.

8) a)

K. Muto, J. Yamaguchi, K. Itami, J. Am. Chem. Soc. 2012, 134, 169.

b)

R. Takise, K. Muto, J. Yamaguchi, K. Itami, Angew. Chem., Int. Ed. 2014, 53, 6791.

c)

E. Koch, R. Takise, A. Studer, J. Yamaguchi, K. Itami, Chem. Commun. 2015, 51, 855.

d)

L. Meng, Y. Kamada, K. Muto, J. Yamaguchi, K. Itami, Angew. Chem., Int. Ed. 2013, 52, 10048.

e)

K. Muto, T. Hatakeyama, J. Yamaguchi, K. Itami, Chem. Sci. 2015, 6, 6792.

9)

Note without reference.

This content is only available as a PDF.
This article is published and distributed under the terms of the Oxford University Press, Standard Journals Publication Model (https://academic.oup.com/pages/standard-publication-reuse-rights)

Supplementary data