SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 10: 3390 - 3398

DOI: https://doi.org/10.6023/cjoc202004044

Silver-Catalyzed Stereoselective Addition of Organic Hypervalent Iodine(III) Reagents to Alkynes

  • Chen Xinyu ,
  • Liu Xueyan ,
  • Ma Fang ,
  • Hong Xianfang ,
  • Li Hongji
Expand
  • a Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000;
    b Bengbu Product Quality and Inspection Institute, Bengbu, Anhui 233040

Received date: 2020-04-27

  Revised date: 2020-06-23

  Online published: 2020-07-01

Supported by

Project supported by the National Natural Science Foundation of China (No. 21772061) and the Natural Science Foundation for the Higher Education Institutions of Anhui Province (No. KJ2017A388).

Fold

Abstract

A silver-catalyzed stereoselective addition reaction of functionalized alkynes with organic hypervalent iodine(Ⅲ) reagents as nucleophiles is reported, providing an approach to vinyl esters in high yields with excellent group tolerance. Intramolecular experiment demonstrates that the presence of aryl group considerably affects the cleavage of I-O bond within hypervalent iodine(Ⅲ) reagents, which is also responsible for the high stereoeselectivity observed in this catalytic system.

Key words： silver catalysis; alkyne; hypervalent(III) iodine reagent; stereoselective addition

Cite this article

Chen Xinyu , Liu Xueyan , Ma Fang , Hong Xianfang , Li Hongji . Silver-Catalyzed Stereoselective Addition of Organic Hypervalent Iodine(III) Reagents to Alkynes[J]. Chinese Journal of Organic Chemistry, 2020 , 40(10) : 3390 -3398 . DOI: 10.6023/cjoc202004044

References

[1] (a) Haines, A. H. Methods for the Oxidation of Organic Compounds. Alkanes, Alkenes, Alkynes, and Arenes, Academic Press, New York, 1985.
(b) Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952.
(c) Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1302.
(d) Gilmore, K.; Alabugin, I. V. Chem. Rev. 2011, 111, 6513.
[2] (a) Wu, W.; Jiang, H. Acc. Chem. Res. 2014, 47, 2483.
(b) Fang, G.; Bi, X. Chem. Soc. Rev. 2015, 44, 8124.
(c) Zhang, F.; Peng, X.; Ma, J. Chin. J. Org. Chem. 2019, 39, 109(in Chinese). (张发光, 彭星, 马军安, 有机化学, 2019, 39, 109.)
(d) Cheng, Z.; Guo, J.; Lu, Z. Chem.Commun.2020, 56, 2229.
(e) Ackermann, L. Acc. Chem. Res. 2020, 53, 84.
[3] (a) Al-awar, R. S.; Joseph, S. P.; Comins, D. L. J. Org. Chem. 1993, 58, 7732.
(b) Kamei, K.; Maeda, N.; Tatsuoka, T. Tetrahedron Lett. 2005, 46, 229.
(c) Spaggiari, A.; Vaccari, D.; Davoli, P.; Torre, G.; Prati, F. J. Org. Chem. 2007, 72, 2216.
(d) Su, W.; Jin, C. Org. Lett. 2007, 9, 993.
(e) Iwai, T.; Fujihara, T.; Terao, J.; Tsuji, Y. J. Am. Chem. Soc. 2012, 134, 1268.
(f) Wu, X.-F.; Bezier, D.; Darcel, C. Adv. Synth. Catal. 2009, 351, 367.
[4] (a) Chen, Z.; Li, J.; Jiang, H.; Zhu, S.; Li, Y.; Qi, C. Org. Lett. 2010, 12, 3262.
(b) Chen, Z.; Jiang, H.; Li, Y.; Qi, C. Chem. Commun. 2010, 46, 8049.
(c) Jiang, G.; Zhu, C.; Li, J.; Wu, W.; Jiang, H. Adv. Synth. Catal. 2017, 359, 1208.
[5] Mo, D.-L.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 2009, 50, 5578.
[6] (a) Wang, S.; Li, P.; Yu, L.; Wang, L. Org. Lett. 2011, 13, 5968.
(b) Hong, X.; Ma, F.; Zha, D.; Li, H. Asian J. Org. Chem. 2018, 7, 2552.
[7] Zeng, X.; Liu, S.; Shi, Z.; Xu, B. Org. Lett. 2016, 18, 4770.
[8] Lu, X.; Zhu, G.; Ma, S. Tetrahedron Lett. 1992, 33, 7205.
[9] (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299.
(b) Charpentier, J.; Früh, N.; Togni, A. Chem. Rev. 2015, 115, 650.
(c) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328.
(d) Duan, Y.; Jiang, S.; Han, Y.; Sun, B.; Zhang, C. Chin. J. Org. Chem. 2016, 36, 1973(in Chinese). (段亚南, 姜山, 韩永超, 孙博, 张弛, 有机化学, 2016, 36, 1973.)
(e) Zhang, H.; Tang, R.; Shi, X.; Xie, L.; Wu, J. Chin. J. Org. Chem. 2019, 39, 1837(in Chinese). (张怀远, 唐蓉萍, 石星丽, 颉林, 伍家卫, 有机化学, 2019, 39, 1837.)
(f) Wang, X.; Studer, A. Acc. Chem. Res. 2017, 50, 1712. For recent examples, see:
(g) Chen, Q.; Yang, Y.; Wang, X.; Zhang, Q.; Li, D. Chin. J. Org. Chem. 2020, 40, 454(in Chinese). (陈倩雯, 杨耀成, 王霞, 张谦, 李栋, 有机化学, 2020, 40, 454.)
(h) Gao, P.; Fan, M.; Bai, Z.; Wei, Y. Chin. J. Chem. 2015, 33, 479.
[10] (a) Frei, R.; Wodrich, M. D.; Hari, D.; Borin, P.; Chauvier, C.; Waser, J. J. Am. Chem. Soc. 2014, 136, 16563.
(b) Zhang, J.; Szabo, K, J.; Himo, F. ACS Catal. 2017, 7, 1093.
(c) Wang, S.; Gu, Q.; You, S. J. Org. Chem. 2017, 82, 11829.
(d) Xia, H.-D.; Zhang, Y.-D.; Wang, Y.-H.; Zhang, C. Org. Lett. 2018, 20, 4052.
(e) Li, J.; Liu, Z.; Wu, S.; Chen, Y. Org. Lett. 2019, 21, 2077.
(f) Li, G.-X.; Hu, X.; He, G.; Chen, G. Chem. Sci. 2019, 10, 688.
(g) Lan, T.; Zhang, Y.; Liu, W.; Xi, C.; Chen, C. Chin. J. Org Chem. 2019, 39, 2166(in Chinese). (兰天磊, 张越, 刘伟, 席婵娟, 陈超, 有机化学, 2019, 39, 2166.)
(h) Liu, Q.-R.; Pan, C.-X.; Ma, X.-P.; Mo, D.-L.; Su, G.-F. J. Org. Chem. 2015, 80, 6496.
(i) Ma, X.-P.; Li, K.; Wu, S.-Y.; Liang, C.; Su, G.-F.; Mo, D.-L. Green Chem. 2017, 19, 5761.
[11] (a) Tan, H.; Li, H.; Ji, W.; Wang, L. Angew. Chem., Int. Ed. 2015, 54, 8374.
(b) Zha, D.; Li, H.; Li, S.; Wang, L. Adv. Synth. Catal. 2017, 359, 467.
(c) Wang, L.; Li, H.; Wang, L. Org. Lett. 2018, 20, 1663.
(d) Yang, S.; Li, H.; Li, P.; Yang, J.; Wang, L. Org. Biomol. Chem 2020, 18, 715.
[12] Deng's group reported a reaction of terminal alkynes with DIB using AgOAc as a catalyst, but which only forms α-acetoxy ketones as sole products. Under Deng's conditions, this stereoselective addition reaction of functionalized alkynes with hypervalent iodine(Ⅲ) reagents does not give the desired product (Entry 2, Table 1). Based on these experiment results, a different pathway for this silver-catalyzed addition is proposed in Scheme 5.
[13] (a) Yamada, W.; Sugawara, Y.; Cheng, H. M.; Ikeno, T.; Yamada, T. Eur. J. Org. Chem. 2007, 16, 2604.
(b) Deng, G.; Luo, J. Tetrahedron 2013, 69, 5937.
[14] Jiang, G.; Li, J. X.; Zhu, C.; Wu, W.; Jiang, H. Org. Lett. 2017, 19, 4440.
Options
Outlines

/

〈 〉