Synthesis of a Zeolitic Imidazolate–Zinc Metal–Organic Framework and the Combination of its Catalytic Properties with 2,2,2-Trifluoroethanol for N-Formylation

Hassan Alamgholiloo; Sadegh Rostamnia; Asadollah Hassankhani; Reza Banaei

doi:10.1055/s-0037-1610159

Synlett, Table of Contents

Synlett 2018; 29(12): 1593-1596
DOI: 10.1055/s-0037-1610159

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Synthesis of a Zeolitic Imidazolate–Zinc Metal–Organic Framework and the Combination of its Catalytic Properties with 2,2,2-Trifluoroethanol for N-Formylation

Hassan Alamgholiloo

^aOrganic and Nano Group (ONG), Department of Chemistry, Faculty of Science, University of Maragheh, PO Box 55181-83111, Maragheh, Iran Email: rostamnia.sadegh@nims.go.jp Email: srostamnia@gmail.com Email: rostamnia@maragheh.ac.ir

,

Sadegh Rostamnia *

^aOrganic and Nano Group (ONG), Department of Chemistry, Faculty of Science, University of Maragheh, PO Box 55181-83111, Maragheh, Iran Email: rostamnia.sadegh@nims.go.jp Email: srostamnia@gmail.com Email: rostamnia@maragheh.ac.ir

,

Asadollah Hassankhani*

^bDepartment of New Materials, Institute of Science and High Technology and Environmental Sciences, Graduate University of Advanced Technology, Kerman, Iran Email: hassankhani_a@yahoo.com

,

Reza Banaei

^aOrganic and Nano Group (ONG), Department of Chemistry, Faculty of Science, University of Maragheh, PO Box 55181-83111, Maragheh, Iran Email: rostamnia.sadegh@nims.go.jp Email: srostamnia@gmail.com Email: rostamnia@maragheh.ac.ir

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Abstract

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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.

Key words

metal–organic frameworks - trifluoroethanol - zeolites - formylation - amines

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References

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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Supplementary Material

Supporting Information