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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

Xiuqiang Lu∗
a   School of Materials and Environmental Engineering, Fujian Polytechnic Normal University, Fuzhou, Fujian 350300, P. R. of China
b   Beijing 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
a   School of Materials and Environmental Engineering, Fujian Polytechnic Normal University, Fuzhou, Fujian 350300, P. R. of China
,
Fei Li∗
c   School of Environment and Chemical Engineering, Shanghai University, Shanghai 200444, P. R. of China
› Author AffiliationsWe are grateful to the National Natural Science Foundation of China (No. 51503037, 12075147), the Natural Science Foundation of Fujian Province (No. 2020J01304), the Program for New Century Excellent Talents in Fujian Province Universities, and the Scientific Research Project for Young and Middle-aged Teachers in Fujian Province (No. JT180633).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1477-4371.
  • Supporting Information


Publication History

Received: 19 February 2021

Accepted after revision: 08 April 2021

Accepted Manuscript online:
08 April 2021

Article published online:
27 April 2021

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  • References

  • 1 Wasielewski MR. Chem. Rev. 1992; 92: 435
    Crossref
    • 2a Kim KS, Lim JM, Osuka A, Kim D. J. Photochem. Photobiol., C 2008; 9: 13
      Crossref
    • 2b Senge MO, Fazekas M, Notaras EG. A, Blau WJ, Zawadzka M, Locos OB, Mhuircheartaigh EM. N. Adv. Mater. 2007; 19: 2737
      Crossref
    • 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
      Crossref
    • 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
      CrossrefPubMed
    • 2f Zeng K, Chen Y, Zhu W.-H, Tian H, Xie Y. J. Am. Chem. Soc. 2020; 142: 5154
      CrossrefPubMed
    • 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
      CrossrefPubMed
    • 2i Tang Y, Wang Y, Yan Q, Zeng K, Tang W, Zhao S, Kong C, Xie Y. Dyes Pigm. 2021; 187: 109075
      Crossref
  • 3 Ouyang Q, Zhu Y.-Z, Zhang C.-H, Yan K.-Q, Li Y.-C, Zheng J.-Y. Org. Lett. 2009; 11: 5266
    CrossrefPubMed
    • 4a Aratani N, Ouska A. Chem. Commun. 2008; 4067
      PubMed
    • 4b Yoshida N, Osuka A. Tetrahedron Lett. 2000; 41: 9287
      Crossref
    • 4c Kamo M, Tsuda A, Nakamura Y, Aratani N, Furukawa K, Kato T, Osuka A. Org. Lett. 2003; 5: 2079
      CrossrefPubMed
    • 4d Sahoo AK, Nakamura Y, Aratani N, Kim KS, Noh SB, Shinokubo H, Kim D, Osuka A. Org. Lett. 2006; 8: 4141
      CrossrefPubMed
  • 5 Osuka A, Shimidzu H. Angew. Chem., Int. Ed. Engl. 1997; 36: 135
    Crossref
  • 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
      Crossref
  • 8 Wojaczyński J, Latos-Grażyński L, Chmielewski PJ, Calcar PV, Balch AL. Inorg. Chem. 1999; 38: 3040
    Crossref
  • 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
    CrossrefPubMed
  • 11 Jin L.-M, Chen L, Yin J.-J, Guo C.-C, Chen Q.-Y. Eur. J. Org. Chem. 2005; 3994
    CrossrefPubMed
  • 12 Lu X.-Q, Guo Y, Chen Q.-Y. Synlett 2011; 77
  • 13 Anastas P, Eghbali N. Chem. Soc. Rev. 2010; 39: 301
    CrossrefPubMed
    • 14a Takacs L. Chem. Soc. Rev. 2013; 42: 7649
      CrossrefPubMed
    • 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
      CrossrefPubMed
    • 14c Hernández JG, Bolm C. J. Org. Chem. 2017; 82: 4007
      CrossrefPubMed
    • 14d Do J.-L, Friščić T. ACS Cent. Sci. 2017; 3: 13
      CrossrefPubMed
    • 14e Achar TK, Bose A, Mal P. Beilstein J. Org. Chem. 2017; 13: 1907
      CrossrefPubMed
    • 14f Howard JL, Cao Q, Browne DL. Chem. Sci. 2018; 9: 3080
      CrossrefPubMed
    • 14g Bolm C, Hernández JG. Angew. Chem. Int. Ed. 2019; 58: 3285
      CrossrefPubMed
    • 14h Friščić T, Mottillo C, Titi HM. Angew. Chem. Int. Ed. 2020; 59: 1018
      CrossrefPubMed
    • 14i Porcheddu A, Colacino E, Luca LD, Delogu F. ACS Catal. 2020; 10: 8344
      Crossref
    • 14j Egorov IN, Santra S, Kopchuk DS, Kovalev IS, Zyryanov GV, Majee A, Ranu BC, Rusinov VL, Chupakhin ON. Green Chem. 2020; 22: 302
      Crossref
    • 14k Stolar T, Uzarević K. CrystEngComm 2020; 22: 4511
      Crossref
    • 15a Rightmire NR, Hanusa TP. Dalton Trans. 2016; 2352
      PubMed
    • 15b Hernández JG. Chem. Eur. J. 2017; 23: 17157
      CrossrefPubMed
  • 17 Stuart DR, Fagnou K. Science 2007; 316: 1172
    CrossrefPubMed
    • 18a Grätz S, Beyer D, Tkachova V, Hellmann S, Berger R, Feng X, Borchardt L. Chem. Commun. 2018; 54: 5307
      CrossrefPubMed
    • 18b Krusenbaum A, Grätz S, Bimmermann S, Hutsch S, Borchardt L. RSC Adv. 2020; 10: 25509
      CrossrefPubMed
    • 18c Grätz S, Oltermann M, Troschke E, Paasch S, Krause S, Brunner E, Borchardt L. J. Mater. Chem. A 2018; 6: 21901
      Crossref