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Synlett 2021; 32(03): 304-308
DOI: 10.1055/a-1277-3995
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
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.
Key words
hypercrosslinked polymer - heterogeneous catalyst - reusable - C–C bond breaking - triarylmethaneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1277-3995.
- Supporting Information
Publication History
Received: 12 July 2020
Accepted after revision: 01 October 2020
Accepted Manuscript online:
01 October 2020
Article published online:
27 November 2020
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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.