Iron Porphyrin Complexes Catalyzed Cyclopropanation Reactions and C-S Bond Cleavage Reactions for Phenyl Vinyl Sulfides and Diazoreagents

doi:10.6023/cjoc202006043

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (11): 3837-3846.DOI: 10.6023/cjoc202006043 Previous Articles Next Articles

Special Issue: 创刊四十周年专辑

铁卟啉类化合物催化乙烯基硫醚和重氮化合物间的环丙烷化和C—S键断裂的竞争反应

闫晓静^a, 李畅^b, 靳智雄^a, 徐孝菲^a, 陈维伟^a, 潘远江^a

a 浙江大学化学系杭州 310027;
b 浙江中医药大学生命科学学院杭州 310053

收稿日期:2020-06-21 修回日期:2020-08-09 发布日期:2020-08-19
通讯作者: 潘远江, 李畅 E-mail:panyuanjiang@zju.edu.cn;lichang@zju.edu.cn
基金资助:
国家科学自然基金（Nos.21532005，21502168）和国家重点研发（No.2016YFF0200503）资助项目.

Iron Porphyrin Complexes Catalyzed Cyclopropanation Reactions and C-S Bond Cleavage Reactions for Phenyl Vinyl Sulfides and Diazoreagents

Yan Xiaojing^a, Li Chang^b, Jin Zhixiong^a, Xu Xiaofei^a, Chen Weiwei^a, Pan Yuanjiang^a

a Departement of Chemistry, Zhejiang University, Hangzhou 310027;
b College of Life Science, Zhejiang Chinese Medical University, Hangzhou 310053

Received:2020-06-21 Revised:2020-08-09 Published:2020-08-19
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21532005, 21502168) and the National Key R&D Program of China (No. 2016YFF0200503).

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Abstract

A catalytic system capable of selectively promoting the cyclopropanation reaction and C—S bond cleavage reaction was established. For the reactions between phenyl vinyl sulfide and diazoacetonitrile (generated by in situ method), the cyclopropanation reaction products were obtained under the catalysis of hemin chloride, and the C—S bond cleavage reaction products were generated in the presence of FePc. All the reations were operated without inert gas protection or high temperature, and the target products were obtained by stirring at room temperature for 1 h in moderate to excellent yields.

Key words: hemin, diazo compound, sulfonium ylide, cyclopropanelation reaction, C-S bond cleavage reaction

Cite this article

Yan Xiaojing, Li Chang, Jin Zhixiong, Xu Xiaofei, Chen Weiwei, Pan Yuanjiang. Iron Porphyrin Complexes Catalyzed Cyclopropanation Reactions and C-S Bond Cleavage Reactions for Phenyl Vinyl Sulfides and Diazoreagents[J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3837-3846.

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[1] (a) Nguyen, T. B. Adv. Synth. Catal. 2017, 359, 1066.
(b) Trost, B. M. Chem. Rev. 1978, 78, 363.
(c) Trost, B. M. Acc. Chem. Res. 1978, 11, 453.
(d) Ranu, B. C.; Jana, R. Adv. Synth. Catal. 2005, 347, 1811.
(e) Peng, H. J.; Cheng, Y. F.; Ni, N. T.; Li, M. Y.; Choudhary, G.; Chou, H. T.; Lu, C. D.; Tai, P. C.; Wang, B. H. ChemMedChem 2009, 4, 1457.
(f) Clayden, J.; MacLellan, P. Beilstein J. Org. Chem. 2011, 7, 582.
(g)Landelle, G.; Panossian, A.; Leroux, F. R. Curr. Top. Med. Chem. 2014, 14, 941.
(h) Screttas, C. G. J. Org. Chem. 1979, 44, 713.
(i) Yin, J. M.; Pidgeon, C. Tetrahedron Lett. 1997, 38, 5953.
(j) Couch, E. D.; Auvil, T. J.; Mattson, A. E. Chem.-Eur. J. 2014, 20, 8283.
(k) Dairo, T. O.; Woo, L. K. Organometallics 2017, 36, 927.
[2] (a) Ahmed, K.; Saikia, G.; Paul, S.; Baruah, S. D.; Talukdar, H.; Sharma, M.; Islam, N. S. Tetrahedron 2019, 75, 130605.
(b) Rayati, S.; Rezaie, S.; Nejabat, F. J. Coord. Chem. 2019, 72, 1466.
(c) Gogoi, S. R.; Boruah, J. J.; Sengupta, G.; Saikia, G.; Ahmed, K.; Bania, K. K.; Islam, N. S. Catal. Sci. Technol. 2015, 5, 595.
(d) Boruah, J. J.; Das, S. P.; Ankireddy, S. R.; Gogoi, S. R.; Islam, N. S. Green Chem. 2013, 15, 2944.
(e) Tamami, B.; Yeganeh, H. Eur. Polym. J. 1999, 35, 1445.
(f) Batigalhia, F.; Zaldini, H. M.; Ferreira, A. G.; Malvestiti, I.; Cass, Q. B. Tetrahedron 2001, 57, 9669.
(g) Ghiron, A. F.; Thompson, R. C. Inorg. Chem. 1989, 28, 3647.
[3] (a) Hock, K. J.; Mertens, L.; Metze, F. K.; Schmittmann, C.; Koenigs, R. M. Green Chem. 2017, 19, 905.
(b) Sun, C.-C.; Xu, K.; Zeng, C.-C. ACS Sustainable Chem. Eng. 2019, 7, 2255.
[4] (a) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195.
(b) Kobayashi, S.; Komiyama, S.; Ishitani, H. Biotechnol. Bioeng. 1998, 61, 23.
(c) Kouznetsov, V. V. Tetrahedron 2009, 65, 2721.
[5] Trost, B. M.; Tanigawa, Y. J. Am. Chem. Soc. 1979, 101, 4743.
[6] Guo, L.; Tu, H.-Y.; Zhu, S.; Chu, L. L. Org. Lett. 2019, 21, 4771.
[7] Seath, C. P.; Vogt, D. B.; Xu, Z.; Boyington, A. J.; Jui, N. T. J. Am. Chem. Soc. 2018, 140, 15525.
[8] (a) Lo, J. C.; Gui, J. H.; Yabe, Y.; Pan, C. M.; Baran, P. S. Nature 2014, 516, 343.
(b) Lo, J. C.; Kim, D.; Pan, C. M.; Edwards, J. T.; Yabe, Y.; Gui, J. H.; Qin, T.; Gutiérrez, S.; Giacoboni, J.; Smith, M. W.; Holland, P. L.; Baran, P. S. J. Am. Chem. Soc. 2017, 139, 2484.
[9] Debien, L.; Braun, M. G.; Quiclet, S. B.; Zard, S. Z. Org. Lett. 2013, 15, 6250.
[10] (a) Liu, J. G.; Ueda, M. J. Mater. Chem. 2009, 19, 8907.
(b) Rodygin, K. S.; Ananikov, V. P. Green Chem. 2016, 18, 482.
[11] (a) Galardon, E.; Le, M. P.; Simonneaux, G. Tetrahedron 2000, 56, 615.
(b) Patil, D. V.; Cavitt, M. A.; Grzybowski, P.; France, S. Chem. Commun. 2011, 47, 10278.
(c) Chawner, S. J.; Cases, T. M. J.; Bull, J. A. Eur. J. Org. Chem. 2017, 5015.
(d) Chandgude, A. L.; Fasan, R. Angew. Chem. Int. Ed. 2018, 57, 15852.
(e) Tinoco, A.; Wei, Y.; Bacik, J. P.; Carminati, D. M.; Moore, E. J.; Ando, N.; Zhang, Y.; Fasan, R. ACS Catal. 2019, 9, 1514.
[12] Schmidt, C. D.; Kaschel, J.; Schneider, T. F.; Kratzert, D.; Stalke, D.; Werz, D. B. Org. Lett. 2013, 15, 6098.
[13] Gryko, D.; Giedyk, M.; Goliszewska, K.; ó Proinsias, K. Chem. Commun. 2016, 52, 1389.
[14] (a) Mehta, V. P.; Modha, S. G.; Van, E. E. J. Org. Chem. 2009, 74, 6870.
(b) Kunchithapatham, K.; Eichman, C. C.; Stambuli, J. P. Chem. Commun. 2011, 47, 12679.
(c) Empel, C.; Hock, K. J.; Koenigs, R. M. Chem. Commun. 2019, 55, 338.
(d) Du, B. N.; Wang, W. M.; Wang, Y.; Qi, Z. H.; Tian, J. Q.; Zhou, J.; Wang, X. C.; Han, J. L.; Ma, J.; Pan, Y. Chem.-Asian J. 2018, 13, 404.
(e) Ghosh, P.; Ganguly, B.; Perl, E.; Das, S. Tetrahedron Lett. 2017, 58, 2751.
(f) Majouga, A. G.; Beloglazkina, E. K.; Moiseeva, A. A.; Shilova, O. V.; Manzheliy, E. A.; Lebedeva, M. A.; Davies, E. S.; Khlobystov, A. N.; Zyk, N. V. Dalton Trans. 2013, 42, 6290.
(g) Desnoyer, A. N.; Love, J. A. Chem. Soc. Rev. 2017, 46, 197.
[15] (a) Sun, R.; Du, Y.; Tian, C.; Li, L.; Wang, H.; Zhao, Y. L. Adv. Syn. Catal. 2019, 361, 5684.
(b) Yan, X. J.; Li, C.; Xu, X. F.; He, Q.; Zhao, X. Y.; Pan, Y. J. Tetrahedron 2019, 75, 3081.
(c) Yan, X. J.; Li, C.; Xu, X. F.; Zhao, X. Y.; Pan, Y. J. Adv. Synth. Catal. 2020, 362, 2005.
[16] (a) Schmink, J. R.; Dockrey, S. A. B.; Zhang, T. Y.; Chebet, N.; Venrooy, A.; Sexton, M.; Lew, S. I.; Chou, S.; Okazaki, A. Org. Lett. 2016, 6360.
(b) Liu, T, Qiu, R. H.; Zhu, L. Z.; Yin, S. F.; Au, C. T.; Kambe, N. Chem.-Asian J. 2018, 13, 3833.
(c) Matt, C.; Kölblin, F.; Streuff, J. Org. Lett. 2019, 21, 6983.
[17] Xu, X. F.; Li, C.; Tao, Z. H.; Pan, Y. J. Adv. Synth. Catal. 2015, 357, 3341.
[18] Xu, X. F.; Li, C.; Tao, Z. H.; Pan, Y. J. Green Chem. 2017, 19, 1245.
[19] Xu, X. F.; Li, C.; Xiong, M. T.; Tao, Z. H.; Pan, Y. J. Chem. Commun. 2017, 53, 6219.
[20] Fu, Y.; Zhang, Y. L.; Gao, Z. H.; Wu, Y. Z.; Zhong, F. R. Org. Biomol. Chem. 2019, 17, 9994.
[21] (a) Vargas, D. A.; Tinoco, A.; Tyagi, V.; Fasan, R. Angew. Chem. Int. Ed. 2018, 57, 9911.
(b) Brandenberg, O. F.; Chen, K.; Arnold, F. H. J. Am. Chem. Soc. 2019, 141, 8989.
(c) Sreenilayam, G.; Fasan, R. Chem. Commun. 2015, 51, 1532.
(d) Lewis, R. D.; Garcia, B. M.; Chalkley, M. J.; Buller, A. R.; Houk. K. N.; Jennifer Kan, S. B.; Arnold, F. H. Proc. Natl. Acad. Sci. 2018, 115, 7308.
(e) Kan, S. B. J.; Lewis, R. D.; Chen, K.; Arnold, F. H. Science 2016, 354, 1048.
[22] (a) Curtius, T. Ber. Dtsch. Chem. Ges. 1898, 31, 2489.
(b) Mykhailiuk, P. K. Eur. J. Org. Chem. 2015, 2015, 7235.
(c) Empel, C.; Hock, K. J.; Koenigs, R. M. Org. Biomol. Chem. 2018, 16, 7129.
[23] Mykhailiuk, P. K.; Koenigs, R. M. Chem.-Eur. J., 2020, 26, 89.
[24] (a) Renata, H.; Lewis, R. D.; Sweredoski, M. J.; Moradian, A.; Hess, S.; Wang, Z. J.; Arnold, F. H. J. Am. Chem. Soc. 2016, 138, 12527.
(b) Li, Y.; Huang, J. S.; Zhou, Z. Y.; Che, C. M.; You, X. Z. J. Am. Chem. Soc. 2002, 124, 13185.
[25] (a) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.
(b) Melvin, L. S. Sulfur Ylides:Emerging Synthetic Intermediates, Academic Press, New York, 1975.
[26] Okimoto, Y.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2002, 124, 1590.

铁卟啉类化合物催化乙烯基硫醚和重氮化合物间的环丙烷化和C—S键断裂的竞争反应

Iron Porphyrin Complexes Catalyzed Cyclopropanation Reactions and C-S Bond Cleavage Reactions for Phenyl Vinyl Sulfides and Diazoreagents

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