Communication
ChemComm
50, 15049; (d) Y.-C. Wu, S.-S. Jiang, S.-Z. Luo, R.-J. Song and J.-H. Li,
Chem. Commun., 2019, 55, 8995; (e) X.-Q. Chu, X.-P. Xu, H. Meng and
S.-J. Ji, RSC Adv., 2015, 5, 67829; ( f ) M.-J. Luo, M. Hu, R.-J. Song,
D.-L. He and J.-H. Li, Chem. Commun., 2019, 55, 1124.
good yields in the presence of NiI2/Ag2CO3 catalyst systems
under heating conditions. This convenient alkylesterification
method may find utility in the synthesis of CH2CN/COO-
containing biologically active compounds.
We thank the Natural Science Foundation of China (No.
51878326, 21762030 and 21861027), Jiangxi Province Science and
Technology Project (No. 20181BAB213002 and 20181BAB203007),
and Jiangxi Educational Committee Foundation of China (No.
GJJ160704) for financial support.
6 (a) X.-W. Lan, N.-X. Wang and Y. Xing, Eur. J. Org. Chem., 2017, 5821;
(b) J. Xuan and A. Studer, Chem. Soc. Rev., 2017, 46, 4329; (c) J. Lin,
R.-J. Song, M. Hu and J.-H. Li, Chem. Rec., 2019, 19, 440;
(d) T. J. Donohoe, C. K. A. Callens, A. Flores, A. R. Lacy and
A. H. Rathi, Chem. – Eur. J., 2011, 17, 58; (e) Y. Yang, R.-J. Song,
X.-H. Ouyang, C.-Y. Wang, J.-H. Li and S. Luo, Angew. Chem., Int. Ed.,
2017, 56, 7916; ( f ) X.-H. Ouyang, R.-J. Song, M. Hu, Y. Yang and
J.-H. Li, Angew. Chem., Int. Ed., 2016, 55, 3187; (g) G. Yin, X. Mu and
G. Liu, Acc. Chem. Res., 2016, 49, 2413; (h) K. Sun, S. Wang, R. Feng,
Y. Zhang, X. Wang, Z. Zhang and B. Zhang, Org. Lett., 2019, 21, 2052.
7 (a) J. Miao and H. Ge, Eur. J. Org. Chem., 2015, 7859; (b) X.-Q. Chu, D. Ge,
Z.-L. Shen and T.-P. Loh, ACS Catal., 2018, 8, 258; (c) S.-R. Guo,
P. S. Kumar and M. Yang, Adv. Synth. Catal., 2017, 359, 2; (d) X.-H.
Yang, R.-J. Song, Y.-X. Xie and J.-H. Li, ChemCatChem, 2016, 8, 2429.
8 C. Chatalova-Sazepin, Q. Wang, G. M. Sammis and J. Zhu, Angew.
Chem., Int. Ed., 2015, 54, 5443.
9 (a) A. Bunescu, Q. Wang and J. Zhu, Angew. Chem., Int. Ed., 2015,
54, 3132; (b) T. Wu, X. Mu and G. Liu, Angew. Chem., Int. Ed., 2011,
50, 12578; (c) X.-W. Lan, N.-X. Wang, C.-B. Bai, C.-L. Lan, T. Zhang,
S.-L. Chen and Y. Xing, Org. Lett., 2016, 18, 5986; (d) F. Wang, X. Qi,
Z. Liang, P. Chen and G. Liu, Angew. Chem., Int. Ed., 2014, 53, 1881;
(e) T. M. Ha, Q. Wang and J. Zhu, Chem. Commun., 2016, 52, 11100;
( f ) T. M. Ha, C. Chatalova-Sazepin, Q. Wang and J. Zhu, Angew.
Chem., Int. Ed., 2016, 55, 9249; (g) A. Bunescu, Q. Wang and J. Zhu,
Chem. – Eur. J., 2014, 20, 14633; (h) A. Bunescu, T. M. Ha, Q. Wang
and J. Zhu, Angew. Chem., Int. Ed., 2017, 56, 10555.
Conflicts of interest
The authors declare no conflict of interest.
Notes and references
1 (a) X. Xing, C. Xu, B. Chen, C. Li, S. C. Virgil and R. H. Grubbs, J. Am.
Chem. Soc., 2018, 140, 17782; (b) F. F. Fleming and Q. Wang, Chem. Rev.,
2003, 103, 2035; (c) M. M˛akosza, Chem. Soc. Rev., 2010, 39, 2855;
(d) M. A. Gouda, B. H. M. Hussein, M. H. Helal and M. A. Salem,
J. Heterocycl. Chem., 2018, 55, 1524; (e) Y. Wang, C. Sha, W. Liu, Y. Gai,
H. Zhang, H. Qu and W. Wang, J. Pharm. Biomed. Anal., 2012, 62, 87;
( f ) L.-H. Lu, Z. Wang, W. Xia, P. Cheng, B. Zhang, Z. Cao and W.-M. He,
Chin. Chem. Lett., 2019, 30, 1237; (g) C. E. Mair, R. Liu, A. G. Atanasov,
L. Wimmer, D. Nemetz-Fiedler, N. Sider, E. H. Heiss, M. D. Mihovilovic,
V. M. Dirsch and J. M. Rollinger, Planta Med., 2015, 81, 1065.
10 Y.-Y. Liu, X.-H. Yang, R.-J. Song, S. Luo and J.-H. Li, Nat. Commun.,
2017, 8, 14720.
ˇ
´
´
2 (a) C. Trefzer, H. Skovierova, S. Buroni, A. Bobovska, S. Nenci,
E. Molteni, F. Pojer, M. R. Pasca, V. Makarov, S. T. Cole, G. Riccardi, 11 (a) X.-H. Ouyang, M. Hu, R.-J. Song and J.-H. Li, Chem. Commun.,
ˇ
´
K. Mikusova and K. Johnsson, J. Am. Chem. Soc., 2012, 134, 912;
(b) F. Zhao, Z. Gao, W. Jiao, L. Chen, L. Chen and X. Yao, Planta
Med., 2012, 78, 1906; (c) H. Chen, J. R. Cox and A. Z. Panagiotopoulos,
2018, 54, 12345; (b) M.-Y. Min, R.-J. Song, X.-H. Ouyang and J.-H. Li,
Chem. Commun., 2019, 55, 3646; (c) Y.-X. Dong, Y. Li, C.-C. Gu,
S.-S. Jiang, R.-J. Song and J.-H. Li, Org. Lett., 2018, 20, 7594.
J. Phys. Chem. B, 2016, 120, 5203; (d) Y.-Z. Yang, R.-J. Song and J.-H. Li, 12 (a) C. Wan, R.-J. Song and J.-H. Li, Org. Lett., 2019, 21, 2800; (b)
Org. Lett., 2019, 21, 3228; (e) C.-C. Wei, Y.-Y. Kong, X. Hua, G.-Q. Li,
S.-L. Zheng, M.-H. Cheng, P. Wang and C.-Y. Miao, Br. J. Pharmacol.,
2017, 174, 3823; ( f ) Y. Gao, C. Li, J. Yin, J. Shen, H. Wang, Y. Wu and
H. Jin, Environ. Toxicol. Pharmacol., 2012, 33, 304.
3 (a) F. Bellina and R. Rossi, Chem. Rev., 2010, 110, 1082;
(b) D. A. Culkin and J. F. Hartwig, Acc. Chem. Res., 2003, 36, 234;
(c) A. Bhunia, K. Bergander and A. Studer, J. Am. Chem. Soc., 2018,
140, 16353; (d) D.-W. Gao, E. V. Vinogradova, S. K. Nimmagadda,
J. M. Medina, Y. Xiao, R. M. Suciu, B. F. Cravatt and K. M. Engle,
J. Am. Chem. Soc., 2018, 140, 8069; (e) X.-H. Ouyang, R.-J. Song and
J.-H. Li, Chem. – Asian J., 2018, 13, 2316; ( f ) W.-H. Bao, M. He,
Z.-M. Chen, X.-M. Zhang and Y.-Q. Tu, Chem. Soc. Rev., 2015,
44, 5220; (c) A. T. Parsons and S. L. Buchwald, Angew. Chem., Int.
Ed., 2011, 50, 9120; (d) R. Zhu and S. L. Buchwald, J. Am. Chem. Soc.,
2015, 137, 8069; (e) Y.-T. He, L.-H. Li, Y.-F. Yang, Z.-Z. Zhou,
H.-L. Hua, X.-Y. Liu and Y.-M. Liang, Org. Lett., 2014, 16, 270;
( f ) F. Wang, D. Wang, X. Mu, P. Chen and G. Liu, J. Am. Chem.
Soc., 2014, 136, 10202; (g) L. Xu, X.-Q. Mou, Z.-M. Chen and
S.-H. Wang, Chem. Commun., 2014, 50, 10676; (h) C. Wu, Z. Wang,
Z. Hu, F. Zeng, X.-Y. Zhang, Z. Cao, Z. Tang, W.-M. He and X.-H. Xu,
Org. Biomol. Chem., 2018, 16, 3177; (i) P. Cheng, W. Wang, L. Wang,
J. Zeng, O. Reiser and Y. Liang, Tetrahedron Lett., 2019, 60, 1408.
J.-T. Wang, X. Peng, M. Sung, Z. Tang, S. Jiang, Z. Cao and W.-M. He, 13 (a) Z. Li, Y. Xiao and Z.-Q. Liu, Chem. Commun., 2015, 51, 9969;
J. Org. Chem., 2019, 84, 6065.
(b) Y. Kawato, N. Kumagai and M. Shibasaki, Chem. Commun., 2013,
49, 11227; (c) G. Dagousset, A. Carboni, E. Magnier and G. Masson,
Org. Lett., 2014, 16, 4340; (d) R. Zhu and S. L. Buchwald, Angew.
Chem., Int. Ed., 2013, 52, 12655; (e) Y. Wang, L. Zhang, Y. Yang,
P. Zhang, Z. Du and C. Wang, J. Am. Chem. Soc., 2013, 135, 18048;
( f ) W. Jian, L. Ge, Y. Jiao, B. Qian and H. Bao, Angew. Chem., Int. Ed.,
2017, 56, 3650; (g) 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.
4 (a) X. Li, J. Xu, Y. Gao, H. Fang, G. Tang and Y. Zhao, J. Org. Chem.,
2015, 80, 2621; (b) M. Hu, M. Li, F.-L. Tan, R.-J. Song, Y.-X. Xie and
J.-H. Li, Adv. Synth. Catal., 2017, 359, 120; (c) M. Hu, H.-X. Zou,
R.-J. Song, J.-N. Xiang and J.-H. Li, Org. Lett., 2016, 18, 6460.
5 (a) Z.-Q. Liu and Z.-J. Li, Chem. Commun., 2016, 52, 14278; (b) Silver
in Organic Chemistry, ed. M. Harmata, Wiley, Hoboken, NJ, 2010;
(c) J. Li, Z. Wang, N. Wu, G. Gao and J. You, Chem. Commun., 2014,
12808 | Chem. Commun., 2019, 55, 12805--12808
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