Communication
Organic & Biomolecular Chemistry
This strategy provides a simple and convenient route for the
difunctionalization of C–C bonds with a phenyl ring and a
sulfonyl radical by the one-pot construction of a C–S bond and
a new C–C bond. Further application of this reaction is
currently underway in our laboratory.
W. E. Truce, J. Org. Chem., 1963, 28, 1420; (f) Y.-Y. Fang,
Z.-G. Luo and X.-M. Xu, RSC Adv., 2016, 6, 59661;
(g) A. N. R. Alba, X. Companyóa and R. Rios, Chem. Soc.
Rev., 2010, 39, 2018.
4 (a) W.-H. Rao, B.-B. Zhan, K. Chen, P.-X. Ling, Z.-Z. Zhang
and B.-F. Shi, Org. Lett., 2015, 17, 3552; (b) M.-J. Cabrera-
Afonso, Z.-P. Lu, C.-B. Kelly, S.-B. Lang, R. Dykstra,
O. Gutierrez and G.-A. Molander, Chem. Sci., 2018, 9, 3186;
Conflicts of interest
(
2
c) R.-J. Song, Y. Liu, Y.-Y. Liu and J.-H. Li, J. Org. Chem.,
011, 76, 1001; (d) L.-Y. Xie, S. Peng, F. Liu, G.-R. Chen,
There are no conflicts to declare.
W. Xia, X.-Y. Yu, W.-F. Li, Z. Cao and W.-M. He, Org. Chem.
Front., 2018, 5, 2604; (e) J. Yang, Y.-Y. Liu, R.-J. Song,
Z.-H. Peng and J.-H. Li, Adv. Synth. Catal., 2016, 358, 2286;
Acknowledgements
(
f) F.-H. Xiao, C. Liu, S.-S. Yuan, H.-W. Huang and
We thank the Scientific Research Fund of the Hunan
Provincial Education Department (No. 16A087), the Natural
Science Foundation of Hunan Province (No. 2018JJ3208) and
the National Natural Science Foundation of China (No.
G.-J. Deng, J. Org. Chem., 2018, 83, 10420.
For reviews, see: (a) A. El-Awa, M.-N. Noshi, X.-M. du
Jourdin and P.-L. Fuchs, Chem. Rev., 2009, 109, 2315;
(
2
Synthesis, Tetrahedron Organic Chemistry Series, Pergamon
Press, New York, 1993, vol. 10.
For selective reviews of C–C activation,
5
6
b) K. Plesniak, A. Zarecki and J. Wicha, Top. Curr. Chem.,
006, 275, 163; (c) N.-S. Simpkins, Sulfones in Organic
2
1602056) for financial support.
Notes and references
see:
1
(a) M. Wang and X.-F. Jiang, Top. Curr. Chem., 2018, 376,
4; (b) M. Wang, Z.-J. Qiao, J.-Y. Zhao and X.-F. Jiang,
Org. Lett., 2018, 20, 6193; (c) Y.-M. Li, W.-S. Xie and
X.-F. Jiang, Chem. – Eur. J., 2015, 21, 16059; (d) Y.-M. Li,
M. Wang and X.-F. Jiang, ACS Catal., 2017, 7, 7587;
(a) B. Rybtchinski and D. Milstein, Angew. Chem., Int. Ed.,
1999, 38, 870; (b) M. Murakami and Y. Ito, Top. Organomet.
Chem., 1999, 3, 97; (c) M.-E. van der Boom and D. Milstein,
Chem. Rev., 2003, 103, 1759; (d) C.-H. Jun, Chem. Soc. Rev.,
2004, 33, 610; (e) T. Satoh and M. Miura, Top. Organomet.
Chem., 2005, 14, 1; (f) C.-H. Jun and J.-W. Park, Top.
Organomet. Chem., 2007, 24, 117; (g) D. Necas and
M. Kotora, Curr. Org. Chem., 2007, 11, 1566;
(h) A. Korotvicka, D. Necas and M. Kotora, Curr. Org.
Chem., 2012, 16, 1170; (i) W.-D. Jones, Nature, 1993, 364,
676; ( j) T. Seiser, T. Saget, D.-N. Tran and N. Cramer,
Angew. Chem., Int. Ed., 2011, 50, 7740; (k) M. Murakami
and T. Matsuda, Chem. Commun., 2011, 47, 1100;
(l) T. Seiser and N. Cramer, Org. Biomol. Chem., 2009, 7,
2835; (m) C. Aïssa, Synthesis, 2011, 3389; (n) M. Murakami
and N. Ishida, J. Am. Chem. Soc., 2016, 138, 13759;
(o) P.-H. Chen, B.-A. Billett, T. Tsukamoto and G. Dong,
ACS Catal., 2017, 7, 1340; (p) A. Dermenci, J.-W. Coe and
G. Dong, Org. Chem. Front., 2014, 1, 567; (q) L. Souillart
and N. Cramer, Chem. Rev., 2015, 115, 9410;
(r) G. Fumagalli, S. Stanton and J.-F. Bower, Chem. Rev.,
2017, 117, 9404.
7 (a) N. Cramer and T. Seiser, Synlett, 2011, 449; (b) T. Seiser,
T. Saget, D.-N. Tran and N. Cramer, Angew. Chem., Int. Ed.,
2011, 50, 7740; (c) Y. Xia, Z.-X. Liu, Z. Liu, R. Ge, F. Ye,
M. Hossain, Y. Zhang and J.-B. Wang, J. Am. Chem. Soc.,
2015, 136, 3013; (d) I. Marek, A. Masarwa, P.-O. Delaye and
M. Leibeling, Angew. Chem., Int. Ed., 2015, 54, 414;
(e) R.-J. Song, Y. Liu, R.-X. Hu, Y.-Y. Liu, J.-C. Wu,
X.-H. Yang and J.-H. Li, Adv. Synth. Catal., 2011, 353, 1467.
8 (a) T. Tsuritani, H. Shinokubo and K. Oshima, Synlett,
2002, 978; (b) S.-C. Wang, D.-M. Troast, M. Conda-
Sheridan, G. Zuo, D. LaGarde, J. Louie and D.-J. Tantillo,
J. Org. Chem., 2009, 74, 7822; (c) G. Zuo and J. Louie,
1
(
(
e) Z.-J. Qiao and X.-F. Jiang, Org. Lett., 2016, 18, 1550;
f) Z.-J. Qiao and X.-F. Jiang, Org. Biomol. Chem., 2017, 15,
1
942; (g) J.-P. Wei, Y.-M. Li and X.-F. Jiang, Org. Lett., 2016,
1
8, 340; (h) P. Dang, Z.-L. Zheng and Y. Liang, J. Org.
Chem., 2017, 82, 2263; (i) W.-J. Liu, H. Min, X.-M. Zhu,
G.-B. Deng and Y. Liang, Org. Biomol. Chem., 2017, 15,
9
804; ( j) H. Min, G.-H. Xiao, W.-J. Liu and Y. Liang,
Org. Biomol. Chem., 2016, 14, 11088.
(a) C. Wu, L.-H. Lu, A.-Z. Peng, G.-K. Jia, C. Peng, Z. Cao,
Z. Tang, W.-M. He and X. Xu, Green Chem., 2018, 20, 3683;
2
(
b) W.-H. Bao, C. Wu, J.-T. Wang, W. Xia, P. Chen, Z. Tang,
X. Xu and W.-M. He, Org. Biomol. Chem., 2018, 16, 8403;
c) L.-Y. Xie, S. Peng, J.-X. Tan, R.-X. Sun, X. Yu, N.-N. Dai,
(
Z.-L. Tang, X. Xu and W.-M. He, ACS Sustainable Chem.
Eng., 2018, 6, 16976; (d) L.-H. Lu, S.-J. Zhou, W.-B. He,
W. Xia, P. Chen, X. Yu, X. Xu and W.-M. He, Org. Biomol.
Chem., 2018, 16, 9064; (e) Z.-J. Qiao, N.-Y. Ge and
X.-F. Jiang, Chem. Commun., 2015, 51, 10295;
(
f) Y.-H. Zhang, Y.-M. Li, X.-M. Zhang and X.-F. Jiang,
Chem. Commun., 2015, 51, 941; (g) G.-Z. Li, H. Xie,
J.-J. Chen, Y.-J. Guo and G.-J. Deng, Green Chem., 2017, 19,
4
043; (h) Y.-J. Xie, X.-G. Chen, Z. Wan, H.-W. Huang, B. Yi
and G.-J. Deng, Green Chem., 2017, 19, 4294.
3
(a) S. Shaaban, S. Liang, N.-W. Liu and G. Manolikakes,
Org. Biomol. Chem., 2017, 15, 1947; (b) C. M. Rayner,
Contemp. Org. Synth., 1994, 1, 191; (c) D.-C. Meadows and
J. Gervay-Hague, Med. Res. Rev., 2006, 26, 793;
(
d) Y. M. Markitanov, V.-M. Timoshenko and Y.-G. Shenko,
J. Sulfur Chem., 2014, 35, 188; (e) H. Fukuda, F. J. Frank and
Org. Biomol. Chem.
This journal is © The Royal Society of Chemistry 2019