Synlett 2021; 32(03): 304-308
DOI: 10.1055/a-1277-3995
letter

Sulfonated Tetraphenylethylene-Based Hypercrosslinked Polymer as a Heterogeneous Catalyst for the Synthesis of Symmetrical Triarylmethanes via a Dual C–C Bond-Cleaving Path

Gitumoni Kalita
,
Namrata Deka
,
Dipankar Paul
,
Loknath Thapa
,
Gitish K. Dutta
,
Department of Chemistry, National Institute of Technology Meghalaya, Bijni Complex, Laitumkhrah, Shillong 793003, Meghalaya, India
› Institutsangaben
The Science and Engineering Research Board (SERB, Grants SB/FT/CS-075/2014 and SB/FT/CS-115/2014) is gratefully acknowledged for financial support to G.K.D. and P.N.C. We also thank NIT Meghalaya for financial support to G.K., N.D., and D.P. SAIF, NEHU.


Abstract

A sulfonic acid functionalized tetraphenylethylene-based hypercrosslinked polymer (THP-SO3H) with a well-developed porous network and accessible sulfonic acid sites was synthesized and characterized by different analytical techniques. The catalytic prowess of the synthesized material THP-SO3H was investigated in a challenging dual C–C bond-breaking reaction for the synthesis of symmetrical triarylmethanes (TRAMs) in high yield. The scope of the developed metal-free method was also explored with a wide variety of substrates. The organocatalyst can be easily recovered by filtration and reused up to five consecutive cycles without substantial loss in its catalytic efficacy.

Supporting Information



Publikationsverlauf

Eingereicht: 12. Juli 2020

Angenommen nach Revision: 01. Oktober 2020

Accepted Manuscript online:
01. Oktober 2020

Artikel online veröffentlicht:
27. November 2020

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References and Notes

    • 1a Guillerm V, Weseliński ŁJ, Alkordi M, Mohideen MI. H, Belmabkhout Y, Cairns AJ, Eddaoudi M. Chem. Commun. 2014; 50: 1937
    • 1b Hao S, Liu Y, Shang C, Liang Z, Yu J. Polym. Chem. 2017; 8: 1833
    • 1c Dawson R, Cooper AI, Adams DJ. Polym. Int. 2013; 62: 345
  • 2 Zhang Y, Riduan SN. Chem. Soc. Rev. 2012; 41: 2083
  • 3 Ahmed DS, El-Hiti GA, Yousif E, Ali AA, Hameed AS. J. Polym. Res. 2018; 25: 75
  • 4 Huang J, Turner SR. Polym. Rev. 2018; 58: 1
  • 5 Davies IW, Matty L, Hughes DL, Reider PJ. J. Am. Chem. Soc. 2001; 123: 10139
  • 6 Bhunia S, Banerjee B, Bhaumik A. Chem. Commun. 2015; 51: 5020
  • 7 Kundu SK, Singuru R, Hayashi T, Hijikata Y, Irle S, Mondal J. ChemistrySelect 2017; 2: 4705
  • 8 Du M, Agrawal AM, Chakraborty S, Garibay SJ, Limvorapitux R, Choi B, Madrahimov ST, Nguyen ST. ACS Sustain. Chem. Eng. 2019; 7: 8126
    • 9a Yao X, Li CJ. J. Org. Chem. 2005; 70: 5752
    • 9b Li H, Li W, Liu W, He Z, Li Z. Angew. Chem. Int. Ed. 2011; 50: 2975
    • 9c Mahoney SJ, Lou T, Bondarenko G, Fillion E. Org. Lett. 2012; 14: 3474
    • 9d Armstrong EL, Grover HK, Kerr MA. J. Org. Chem. 2013; 78: 10534
    • 9e Yang Y, Ni F, Shu WM, Wu AX. Chem. Eur. J. 2014; 20: 11776
    • 9f Yao Q, Kong L, Wang M, Yuan Y, Sun R, Li Y. Org. Lett. 2018; 20: 1744
    • 9g Yao Q, Kong L, Zhang F, Tao X, Li Y. Adv. Synth. Catal. 2017; 359: 3079
    • 9h Cheng X, Zhou Y, Zhnag F, Zhu K, Liu Y, Li Y. Chem. Eur. J. 2016; 22: 12655
    • 9i Zhou Y, Tao X, Yao Q, Zhao Y, Li Y. Chem. Eur. J. 2016; 22: 17936
  • 10 Paul D, Khatua S, Chatterjee PN. New J. Chem. 2019; 43: 10056
    • 11a Esquivias J, Gomez Arrayas R, Carretero JC. Angew. Chem. Int. Ed. 2006; 45: 629
    • 11b Mondal S, Panda G. RSC Adv. 2014; 4: 28317
    • 11c Yue C, Na F, Fang X, Cao Y, Antilla JC. Angew. Chem. Int. Ed. 2018; 57: 11004
    • 11d Zhang Z, Wang H, Qiu N, Kong Y, Zeng W, Zhang Y, Zhao J. J. Org. Chem. 2018; 83: 8710
  • 12 Lee J. -SM, Briggs ME, Hasell T, Copper AI. Adv. Mater. 2016; 28: 9804
    • 13a Nambo M, Crudden CM. ACS Catal. 2015; 5: 4734
    • 13b Praveen PJ, Parameswaran PS, Majik MS. Synthesis 2015; 47: 1827
    • 13c Shiri M, Zolfigol MA, Kruger HG, Tanbakouchian Z. Chem. Rev. 2010; 110: 2250
  • 14 Zeng JH, Wang YF, Gou SQ, Zhang LP, Chen Y, Jiang JX, Shi F. ACS Appl. Mater. Interfaces 2017; 9: 34783
  • 15 The following unsymmetrical TRAM (via only Csp3–Csp3 bond cleavage) was not isolated in the reaction (Figure 3).
  • 16 Luo Y. -R, Kerr J. In CRC Handbook of Chemistry and Physics. 93rd ed. . Haynes WM. CRC Press; Boca Raton: 2012: 89
    • 17a Thirupathi P, Soo Kim S. J. Org. Chem. 2010; 75: 5240
    • 17b Castellani CB, Perotti A, Scrivanti M, Vidari G. Tetrahedron 2000; 56: 8161
  • 18 Typical Procedure for the Synthesis of 3aA 25 mL round-bottomed flask equipped with a magnetic bar and water condenser were charged with 1a (1.0 mmol), 2a (3.0 mmol), DCE (2.0 mL), and THP-SO3H (96 mg) in an air atmosphere. The flask was placed in a constant temperature oil bath at 80 °C, and the progress of the reaction was monitored by TLC. After 30 min, the mixture was filtered to separate the catalyst and washed twice with DCE (2 × 5 mL). Then the filtrate was removed under reduced pressure, and the crude product was purified by dry column vacuum chromatography (silica gel G, petroleum ether 60–80 °C/EtOAc) to give a yellow oily liquid; yield 94%.1H NMR (400 MHz, CDCl3): δ = 2.158 (s, 6 H), 5.256 (s, 1 H), 5.788 (d, J = 3.2 Hz, 4 H), 7.159–7.243 (m, 5 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 13.65, 45.12, 106.08, 108.19, 126.97, 128.40, 128.44, 140.00, 151.46, 152.85 ppm.