Please do not adjust margins
RSC Advances
Page 4 of 6
COMMUNICATION
RSC Advances
Synthesis, 2012, 1526.
bearing electron-donating groups easily made radical
stable, which was benefit for the radical coupling. Contrarily,
when the benzene ring was substituted by electron-
A more
8
9
H.-Y. Fei, J.-T. Yu, Y. Jiang, H. Guo and JD. OChI:e10n.g10, 3O9r/gC.6BRiAo0m13o9l3.G
Chem., 2013, 11, 7092.
withdrawing groups, radical
which made the yield decreased. Obviously, the bigger steric
hindrance was adverse for both the stability of radical and
the coupling reaction with radical , so the yield was reduced.
A easily became more unstable,
(a) T. Kawakami and H. Suzuki, Tetrahedron Lett., 2000, 41
7093; (b) G.-B. Chu, Z.-F. Yu, F. Gao and C.-B. Li, Synth.
Commun., 2013, 43, 44.
,
A
10 X.-Y. Ren, J.-B. Chen, F. Chen and J. Cheng, Chem. Commun.,
2011, 47, 6725.
D
In conclusion, without the needs of anaerobic atmosphere,
the utilization of DMSO as one-carbon synthon was developed
for the first time. In addition, the temperature is not high, the
condition is mild. The detailed mechanistic studies showed
that this transformation was involved in the radical coupling
reaction of DMSO with sodium arylsulfinates. This protocol
may provide new opportunities in organic synthesis for the
comprehensive utilization of organic sulphur oxides, such as
sulfoxides27 and sodium sulfinates. Further study on this topic
is currently undergoing in our laboratory.
11 Y.-H. Lv, Y. Li, T. Xiong, W.-Y. Pu, H.-W. Zhang, K. Sun, Q. Liu
and Q. Zhang, Chem. Commun., 2013, 49, 6439.
12 (a) X.-S. Wu, Y. Chen, M.-B. Li, M.-G. Zhou and S.-K. Tian, J.
Am. Chem. Soc., 2012, 134, 14694; (b) F.-H. Xiao, H. Xie, S.-W.
Liu and G.-J. Deng, Adv. Synth. Catal., 2014, 356, 364; (c) V. G.
Pandya and S. B. Mhaske, Org. Lett., 2014, 16, 3836; (d) H.-S.
Li and G. Liu, J. Org. Chem., 2014, 79, 509; (e) K. Yang, M.-L.
Ke, Y.-G. Lin and Q.-L. Song, Green Chem., 2015, 17, 1395; (f)
N. Taniguchi, J. Org. Chem., 2015, 80, 1764; (g) S. Sun, J.-T.
Yu, Y. Jiang and J. Cheng, Adv. Synth. Catal., 2015, 357, 2022;
(h) C. Buathongjan, D. Beukeaw and S. Yotphan, Eur. J. Org.
Chem., 2015, 1575; (i) W.-H. Rao and B.-F. Shi, Org. Lett.,
2015, 17, 2784; (j) A. C. M. A. Nassoy, P. Raubo and J. P. A.
Harrity, Chem. Commun., 2015, 51. 5914.
13 (a) X.-D. Tang, L.-B. Huang, Y.-L. Xu, J.-D. Yang, W.-Q. Wu and
H.-F. Jiang, Angew. Chem., Int. Ed., 2014, 53, 4205; (b) Y.-L.
Xu, J.-W. Zhao, X.-D. Tang, W.-Q. Wu and H.-F. Jiang, Adv.
Synth. Catal., 2014, 356, 2029; (c) Y.-L. Xu, X.-D. Tang, W.-G.
Hu, W.-Q. Wu and H.-F. Jiang, Green Chem., 2014, 16, 3720;
(d) X.-J. Pan, J. Gao, J. Liu, J.-Y. Lai, H.-F. Jiang and G.-Q. Yuan,
Green Chem., 2015, 17, 1400.
Acknowledgements
The authors thank Guangdong NSF (Nos. 2014A030313429,
S2011010001556), the 3rd Talents Special Funds of Guangdong
Higher
Education
(No.
Guangdong-Finance-Education
[2011]431) and NNSFC (No. 20772035) for financial support.
14 (a) Q. Jiang, B. Xu, J. Jia, A. Zhao, Y.-R. Zhao, Y.-Y. Li, N.-N. He
and C.-C. Guo, J. Org. Chem., 2014, 79, 7372; (b) F.-H. Xiao, H.
Chen, H. Xie, S.-Q. Chen, L. Yang and G.-J. Deng, Org. Lett.,
2014, 16, 50; (c) B. Yang, X.-H. Xu and F.-L. Qing, Org. Lett.,
2015, 17, 1906; (d) J.-D. Liu, L. Yu, S.-B. Zhuang, Q.-W. Gui, X.
Notes and references
1
H. D. Martin, A. Weise and H. J. Niclas, Angew. Chem., Int.
Ed., 1967, , 318.
(a) W. W. Epstein and F. W. Sweat, Chem. Rev., 1967, 67, 247;
(b) T. T. Tidwell, Synthesis, 1990, 857; (c) S. Song, X.-W. Li, X.
Sun, Y.-Z. Yuan and N. Jiao, Green Chem., 2015, 17, 3285; (d)
S. Song, X. Sun, X.-W. Li, Y.-Z. Yuan and N. Jiao, Org. Lett.,
2015, 17, 2886.
6
2
Chen, W.-D. Wang and Z. Tan, Chem. Commun., 2015, 51
,
6418; (e) Y. Yang, Y.-L. Liu, Y. Jiang, Y. Zhang and D. A. Vicic, J.
Org. Chem., 2015, 80, 6639; (f) K. Zhang, X.-H. Xu and F.-L.
Qing, J. Org. Chem., 2015, 80, 7658; (g) N. Taniguchi, J. Org.
Chem., 2015, 80, 7797.
3
4
X. Jiang, C. Wang, Y.-W. Wei, D. Xue, Z.-T. Liu and J.-L. Xiao,
Chem. Eur. J., 2014, 20, 58.
(a) L.-L. Chu, X.-Y. Yue and F.-L. Qing, Org. Lett., 2010, 12
1644; (b) F. Luo, C.-D. Pan, L.-P. Li, F. Chen and J. Cheng,
Chem. Commun., 2011, 47, 5304; (c) C. Dai, Z.-Q. Xu, F.
15 (a) A. U. Meyer, S. Jäger, D. P. Hari and B. König, Adv. Synth.
Catal., 2015, 357, 2050; (b) F.-H. Xiao, S.-Q. Chen, Y. Chen,
H.-W. Huang and G.-J. Deng, Chem. Commun., 2015, 51, 652;
(c) G.-W. Rong, J.-C. Mao, H. Yan, Y. Zheng and G.-Q. Zhang, J.
Org. Chem., 2015, 80, 7652.
,
Huang, Z.-K. Yu and Y.-F. Gao, J. Org. Chem., 2012, 77, 4414;
(d) S. M. Patil, S. Kulkarni, M. Mascarenhas, R. Sharma, S. M.
Roopan and A. Roychowdhury, Tetrahedron, 2013, 69, 8255;
(e) F.-L. Liu, J.-R. Chen, Y.-Q. Zou, Q. Wei and W.-J. Xiao, Org.
Lett., 2014, 16, 3768; (f) P. Sharma, S. Rohilla and N. Jain, J.
Org. Chem., 2015, 80, 4116; (g) H.-Y. Li, L.-J. Xing, M.-M. Lou,
H. Wang, R.-H. Liu and B. Wang, Org. Lett., 2015, 17, 1098.
(a) R.-S. Xu, J.-P. Wan, H. Mao and Y.-J. Pan, J. Am. Chem.
Soc., 2010, 132, 15531; (b) Y. Ashikari, T. Nokami and J.
Yoshida, J. Am. Chem. Soc., 2011, 133, 11840; (c) R. Tomita, Y.
16 (a) Y.-H. Tan, J.-X. Li, F.-L. Xue, J. Qi and Z.-Y. Wang,
Tetrahedron, 2012, 68, 2827; (b) J.-P. Huo, P. Peng, G.-H.
Deng, W. Wu, J.-F. Xiong, M.-L. Zhong and Z.-Y. Wang,
Macromol. Rapid Commun., 2013, 34, 1779; (c) J.-P. Huo, J.-C.
Luo, W. Wu, J.-F. Xiong, G.-Z. Mo and Z.-Y. Wang, Ind. Eng.
Chem. Res., 2013, 52, 11850; (d) F.-L. Xue, P. Peng, J. Shi, M.-
L. Zhong and Z.-Y. Wang, Synth. Commun., 2014, 44, 1944; (e)
Y.-T. Tan, J.-X. Li, J.-P. Huo, F.-L. Xue and Z.-Y. Wang. Synth.
Commun., 2014, 44, 2974; (f) P. Peng, M.-H. Feng, J. Shi, J.-L.
Zheng, Y.-C. Wu, Z.-Y. Wang and R.-H. Chen. Lett. Org. Chem.,
2015, 12, 359.
5
Yasu, T. Koike and M. Akita, Angew. Chem., Int. Ed., 2014, 53
7144; (d) Y.-F. Liang, K. Wu, S. Song, X.-Y. Li, X.-Q. Huang and
N. Jiao, Org. Lett., 2015, 17, 876.
,
17 J. Shi, X.-D. Tang, Y.-C. Wu, H.-N. Li, L.-J. Song and Z.-Y. Wang,
Eur. J. Org. Chem., 2015, 1193.
18 (a) Q.-H. Zhou, A. Ruffoni, R. Gianatassio, Y. Fujiwara, E. Sella,
6
7
(a) Y.-J. Jiang and T.-P. Loh, Chem. Sci., 2014,
5, 4939; (b) G.-
Q. Yuan, J.-H. Zheng, X.-F. Gao, X.-W. Li, L.-B. Huang, H.-J.
D. Shabat and P. S. Baran, Angew. Chem., Int. Ed., 2013, 52
,
Chen and H.-F. Jiang, Chem. Commun., 2012, 48, 7513; (c) X.-
F. Gao, X.-J. Pan, J. Gao, H.-W. Huang, G.-Q. Yuan and Y.-W. Li,
Chem. Commun., 2015, 51, 210.
(a) H. Cao, S. Lei, N.-Y. Li, L.-B. Chen, J.-Y. Liu, H.-Y. Cai, S.-X.
Qiu and J.-W. Tan, Chem. Commun., 2015, 51, 1823; (b) Z.-G.
Zhang, Q. Tian, J.-J. Qian, Q.-F. Liu, T.-X. Liu, L. Shi and G.-S.
Zhang, J. Org. Chem., 2014, 79, 8182; (c) J.-J. Qian, Z.-G.
Zhang, Q.-F. Liu, T.-X. Liu and G.-S. Zhang, Adv. Synth. Catal.,
3949; (b) S. C. Cullen, S. Shekhar and N. K. Nere, J. Org.
Chem., 2013, 78, 12194; (c) Y.-M. Su, Y. Hou, F. Yin, Y.-M. Xu,
Y. Li, X.-Q. Zheng and X.-S. Wang, Org. Lett., 2014, 16, 2958;
(d) J.-Y. Wang, X. Zhang, Y. Bao, Y.-M. Xu, X.-F. Cheng and X.-
S. Wang, Org. Biomol. Chem., 2014, 12, 5582; (e) W.-J. Miao,
C.-F. Ni, Y.-C. Zhao and J.-B. Hu, J. Fluorine Chem., 2014, 167
231; (f) M. D. Korzyński, K. M. Borys, J. Bialek and Z. Ochal,
Tetrahedron Lett., 2014, 55, 745.
,
X| RSC Adv., XXXX, XX, X-X
This journal is © The Royal Society of Chemistry 2016
Please do not adjust margins