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Synlett 2018; 29(12): 1593-1596
DOI: 10.1055/s-0037-1610159
DOI: 10.1055/s-0037-1610159
letter
Synthesis of a Zeolitic Imidazolate–Zinc Metal–Organic Framework and the Combination of its Catalytic Properties with 2,2,2-Trifluoroethanol for N-Formylation
Further Information
Publication History
Received: 11 January 2018
Accepted after revision: 25 April 2018
Publication Date:
30 May 2018 (online)
Abstract
A novel protocol is reported for the N-formylation of amines with formic acid by using the nanoporous zeolitic imidazolate framework ZIF-8 as a heterogeneous catalyst in 2,2,2-trifluoroethanol.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610159.
- Supporting Information
-
References and Notes
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- 30 N-Formylation: General Procedure The appropriate amine (1 mmol), HCO2H (3 mmol), and ZIF-8 (5 mg, 3 mol%) were added to TFE (3 mL), and the mixture was stirred at 40 °C for the appropriate time (Table 2). When the reaction was complete (TLC), the catalyst was recovered by centrifugation, and the TFE was recovered by distillation (bp 78 °C). The resulting mixture was then purified by column chromatography (silica gel) to provide the desired product. The structures of all products were confirmed by 1H and 13C NMR spectroscopy (see Supporting Information). N-Phenylformamide (3a) White solid; yield: 120 mg (>99%); mp 45 °C. 1H NMR (300 MHz, CDCl3): δ = 7.28 (m, 3 H, CH of Ar), 7.57 (d, 3 J HH = 8.4 Hz, 2 H), 8.33 (s, 1 H, H of CHO), 9.15 (br s, 1 H, NH). N,N-Diphenylacetamide (3f)White solid; yield: 196 mg (93%); mp 101 °C. 1H NMR (300 MHz, CDCl3): δ = 2.09 (s, 3 H, CH3), 6.96–7.37 (m, 10 H, CH of Ar).
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