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Organic & Biomolecular Chemistry
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Journal Name
COMMUNICATION
Chem., 2010,
2
intermediate
gives the biaryl product
C. Finally, the deprotonation of intermediate C
K. H. Chung, C. He, H. Wang, F. Y. KwDoOnIg: 1a0n.1d03VA9ie/.wCL7AeOrtii,Bcl0Je.1O5An6lmi4nJe.
Chem. Soc., 2010, 132, 16737. (d) E. Shirakawa, K.-I. Itoh, T.
3
.
Higashino and T. Hayashi, J. Am. Chem. Soc., 2010, 132
,
15537. (e) J. Cuthbertson, V. J. Gray and J. D. Wilden, Chem.
Commun., 2014, 50, 2575. (f) Y. Gao, P. Tang, H. Zhou, W.
Zhang, H. Yang, N. Yan, G. Hu, D. Mei, J. Wang and D. Ma,
Angew. Chem., Int. Ed., 2016, 55, 3124. (g) C.-L. Sun, Y.-F. Gu,
W.-P. Huang and Z.-J. Shi, Chem. Commun., 2011, 47, 9813.
(h) Z. Xu, L. Gao, L. Wang, M. Gong, W. Wang and R. Yuan,
ACS Catal., 2015, 5, 45. (i) W.-C. Chen, Y.-C. Hsu, W.-C. Shih,
C.-Y. Lee, W.-H. Chuang, Y.-F. Tsai, P. P.-Y. Chen and T.-G.
Ong, Chem. Commun., 2012, 48, 6702. (j) A. Dewanji, S.
Scheme 4. Kinetic isotope experiment
Murarka, D. P. Curran and A. Studer, Org. Lett., 2013, 15
,
6102. (k) Q. Song, D. Zhang, Q. Zhu and Y. Xu, Org. Lett., 2014,
16, 5272. (l) M. Patil, J. Org. Chem., 2016, 81, 632. (m) L.
Zhang, H. Yang and L. Jiao, J. Am. Chem. Soc., 2016, 138
,
7151. (n) J. P. Barham, G. Coulthard, K. J. Emery, E. Doni, F.
Cumine, G. Nocera, M. P. John, L. E. A. Berlouis, T. McGuire,
T. Tuttle and J. A. Murphy, J. Am. Chem. Soc., 2016, 138
,
7402. (o) H. Zhao, J. Shen, C. Ren, W. Zeng and H. Zeng, Org.
Lett., 2017, 19, 2190.
6
7
A. Kumar and B. A. Shah, Org. Lett., 2015, 17, 5232.
Reviews: (a) O. Baudoin, Angew. Chem., Int. Ed., 2007, 46
,
1373. (b) N. Rodrıguez and L. J. Gooßn, Chem. Soc. Rev., 2011,
40, 5030 (c) R. Shang and L. Liu, Sci. China: Chem., 2011, 54
,
1670. (d) Y. Wei, P. Hu, M. Zhang and W. Su, Chem. Rev.,
2017, 117, 8864.
(a) W. Y. Yu, W. N. Sit, Z. Zhou and A. S. C. Chan, Org. Lett.,
2009, 11, 3174. (b) D. Li, N. Xu, Y. Zhang and L. Wang, Chem.
Commun., 2014, 50, 14862. (c) M. Sun, Z. Wang, J. Wang, P.
Scheme 5. Proposed mechanism.
8
In conclusion, we have disclosed a direct arylation of
unactivated benzene with acyl peroxides affording the biaryls
in good to excellent yields. This transformation went through
radical pathway under metal-free, base-free and additive-free
conditions with good functional groups compatibility.
Compared with previous methods toward biaryls, this
procedure is more simple, mild and environment friendly.
We thank the National Natural Science Foundation of China
(21602086 and 21672028), the Natural Science Foundation for
Colleges and Universities of Jiangsu Province (16KJB150002)
and Jiangsu Key Laboratory of Advanced Catalytic Materials &
Technology (BM2012110) for financial supports.
Guo, X. Chen and Y.-M. Li, Org. Biomol. Chem., 2016, 14
,
10585. (d) C. Qian, D. Lin, Y. Deng, X.-Q. Zhang, H. Jiang, G.
Miao, X. Tang and W. Zeng, Org. Biomol. Chem., 2014, 12
,
,
5866. (e) K. R. Babu, N. Zhu and H. Bao, Org. Lett., 2017, 19
46.
9
C. Pan, H. Zhang, J. Han, Y. Cheng and C. Zhu, Chem.
Commun., 2015, 51, 3786.
10 The reaction of bis-3,4-dichlorobenzoyl peroxide with
benzene utilizing m-dinitro-benzene as additive, see: D. H.
Hey and M. J. Perkins, Org. Synth., 1969, 49, 44.
11 C. Pan, Y. Fu, Q. Ni and J.-T. Yu, J. Org. Chem., 2017, 82, 5005.
Notes and references
1
(a) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz and M. Lemaire,
Chem. Rev., 2002, 102, 1359. (b) P. J. Hajduk, M. Bures, J.
Praestgaard and S. W. Fesik, J. Med. Chem., 2000, 43, 3443.
(a) A. Suzuki, Angew. Chem., Int. Ed., 2011, 50, 6722. (b) E.
Negishi, Angew. Chem., Int. Ed., 2011, 50, 6738. (c) Y. Nakao
and T. Hiyama, Chem. Soc. Rev., 2011, 40, 4893. (d) J. K. Stille,
Angew. Chem., Int. Ed., 1986, 25, 508. (e) C. E. I. Knappke
and A. J. V. Wangelin, Chem. Soc. Rev., 2011, 40, 4948. (f) D.
2
Alberico, M. E. Scott and M. Lautens, Chem. Rev., 2007, 107
,
174. (g) G. P. McGlacken and L. M. Batemana, Chem. Soc.
Rev., 2009, 38, 2447. (h) L. Ackermann, R. Vicente and A. R.
Kapdi, Angew. Chem., Int. Ed., 2009, 48, 9792.
3
4
C.-L. Sun and Z.-J. Shi, Chem. Rev., 2014, 114, 9219.
(a) W. R. Bowman and J. M. D. Storey, Chem. Soc. Rev., 2007,
36, 1803. (b) S. Yanagisawa and K. Itami, ChemCatChem,
2011,
Int. Ed., 2011, 50, 5018. (d) A. Studer and D. P. Curran, Nat.
Chem., 2014, , 765.
3, 827. (c) A. Studer and D. P. Curran, Angew. Chem.
6
5
(a) S. Yanagisawa, K. Ueda, T. Taniguchi and K. Itami, Org.
Lett., 2008, 10, 4673. (b) C.-L. Sun, H. Li, D.-G. Yu, M. Yu, X.
Zhou, X.-Y. Lu, K. Huang, S.-F. Zheng, B.-J. Li and Z.-J. Shi, Nat.
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