Synthesis of Diporphyrins by Oxidative Coupling with Pd(TFA)2-Cu(OTf)2 under Ball-Milling Conditions

Xiuqiang Lu; Guofen Chen; Fei Li

doi:10.1055/a-1477-4371

Synthesis, Table of Contents

Synthesis 2021; 53(15): 2651-2655
DOI: 10.1055/a-1477-4371

paper

Synthesis of Diporphyrins by Oxidative Coupling with Pd(TFA)₂-Cu(OTf)₂ under Ball-Milling Conditions

Authors

Xiuqiang Lu∗

^aSchool of Materials and Environmental Engineering, Fujian Polytechnic Normal University, Fuzhou, Fujian 350300, P. R. of China

^bBeijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
Guofen Chen

^aSchool of Materials and Environmental Engineering, Fujian Polytechnic Normal University, Fuzhou, Fujian 350300, P. R. of China
Fei Li∗

^cSchool of Environment and Chemical Engineering, Shanghai University, Shanghai 200444, P. R. of China

Abstract

All articles of this category

Abstract

A sustainable synthetic method for the synthesis of diporphyrins under ball-milling conditions is reported. The meso-meso linked diporphyrins are efficiently accessed by direct oxidative homo-coupling of porphyrins with Pd(TFA)₂ as the catalyst and Cu(OTf)₂ as the oxidant.

Key words

diporphyrins - oxidative coupling - sustainable chemistry - ball-milling - mechanochemistry

Full Text

References

References
1 Wasielewski MR. Chem. Rev. 1992; 92: 435

2a Kim KS, Lim JM, Osuka A, Kim D. J. Photochem. Photobiol., C 2008; 9: 13
2b Senge MO, Fazekas M, Notaras EG. A, Blau WJ, Zawadzka M, Locos OB, Mhuircheartaigh EM. N. Adv. Mater. 2007; 19: 2737
2c Sitte E, Senge MO. Eur. J. Org. Chem. 2020; 3171
2d Chen Y, Zeng K, Li C, Liu X, Xie Y. J. Porphyrins Phthalocyanines 2019; 24: 401
2e Li Q, Li C, Baryshnikov G, Ding Y, Zhao C, Gu T, Sha F, Liang X, Zhu W, Wu X, Ågren H, Sessler JL, Xie Y. Nat. Commun. 2020; 11: 5289
2f Zeng K, Chen Y, Zhu W.-H, Tian H, Xie Y. J. Am. Chem. Soc. 2020; 142: 5154
2g Zeng K, Tong Z, Ma L, Zhu W.-H, Wu W, Xie Y. Energy Environ. Sci. 2020; 1617
2h Zou J, Yan Q, Li C, Lu Y, Tong Z, Xie Y. ACS Appl. Mater. Interfaces 2020; 12: 57017
2i Tang Y, Wang Y, Yan Q, Zeng K, Tang W, Zhao S, Kong C, Xie Y. Dyes Pigm. 2021; 187: 109075

3 Ouyang Q, Zhu Y.-Z, Zhang C.-H, Yan K.-Q, Li Y.-C, Zheng J.-Y. Org. Lett. 2009; 11: 5266

4a Aratani N, Ouska A. Chem. Commun. 2008; 4067
4b Yoshida N, Osuka A. Tetrahedron Lett. 2000; 41: 9287
4c Kamo M, Tsuda A, Nakamura Y, Aratani N, Furukawa K, Kato T, Osuka A. Org. Lett. 2003; 5: 2079
4d Sahoo AK, Nakamura Y, Aratani N, Kim KS, Noh SB, Shinokubo H, Kim D, Osuka A. Org. Lett. 2006; 8: 4141

5 Osuka A, Shimidzu H. Angew. Chem., Int. Ed. Engl. 1997; 36: 135
6 Ogawa T, Nishimoto Y, Yoshida N, Ono N, Osuka A. Chem. Commun. 1998; 337

7a Shi X, Liebeskind LS. J. Org. Chem. 2000; 65: 1655
7b Senge MO, Feng X. Tetrahedron Lett. 1999; 40: 4165

8 Wojaczyński J, Latos-Grażyński L, Chmielewski PJ, Calcar PV, Balch AL. Inorg. Chem. 1999; 38: 3040
9 Jin L.-M, Yin J.-J, Chen L, Guo C.-C, Chen Q.-Y. Synlett 2005; 2893
10 Ogawa T, Nishimoto Y, Yoshida N, Ono N, Osuka A. Angew. Chem. Int. Ed. 1999; 38: 176
11 Jin L.-M, Chen L, Yin J.-J, Guo C.-C, Chen Q.-Y. Eur. J. Org. Chem. 2005; 3994
12 Lu X.-Q, Guo Y, Chen Q.-Y. Synlett 2011; 77
13 Anastas P, Eghbali N. Chem. Soc. Rev. 2010; 39: 301

14a Takacs L. Chem. Soc. Rev. 2013; 42: 7649
14b James SL, Adams CJ, Bolm C, Braga D, Collier P, Friščić T, Grepioni F, Harris KD. M, Hyett G, Jones V, Krebs A, Mack J, Maini L, Orpen AG, Parkin IP, Shearouse WC, Steed JW, Waddell DC. Chem. Soc. Rev. 2012; 41: 413
14c Hernández JG, Bolm C. J. Org. Chem. 2017; 82: 4007
14d Do J.-L, Friščić T. ACS Cent. Sci. 2017; 3: 13
14e Achar TK, Bose A, Mal P. Beilstein J. Org. Chem. 2017; 13: 1907
14f Howard JL, Cao Q, Browne DL. Chem. Sci. 2018; 9: 3080
14g Bolm C, Hernández JG. Angew. Chem. Int. Ed. 2019; 58: 3285
14h Friščić T, Mottillo C, Titi HM. Angew. Chem. Int. Ed. 2020; 59: 1018
14i Porcheddu A, Colacino E, Luca LD, Delogu F. ACS Catal. 2020; 10: 8344
14j Egorov IN, Santra S, Kopchuk DS, Kovalev IS, Zyryanov GV, Majee A, Ranu BC, Rusinov VL, Chupakhin ON. Green Chem. 2020; 22: 302
14k Stolar T, Uzarević K. CrystEngComm 2020; 22: 4511

15a Rightmire NR, Hanusa TP. Dalton Trans. 2016; 2352
15b Hernández JG. Chem. Eur. J. 2017; 23: 17157

16a Štrukil V. Synlett 2018; 29: 1281
16b Waghmare DS, Tambe SD, Kshirsagar UA. Asian J. Org. Chem. 2020; 9: 2095

17 Stuart DR, Fagnou K. Science 2007; 316: 1172

18a Grätz S, Beyer D, Tkachova V, Hellmann S, Berger R, Feng X, Borchardt L. Chem. Commun. 2018; 54: 5307
18b Krusenbaum A, Grätz S, Bimmermann S, Hutsch S, Borchardt L. RSC Adv. 2020; 10: 25509
18c Grätz S, Oltermann M, Troschke E, Paasch S, Krause S, Brunner E, Borchardt L. J. Mater. Chem. A 2018; 6: 21901

Supplementary Material

Supporting Information (PDF)