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Synlett 2024; 35(16): 1914-1918
DOI: 10.1055/a-2272-8045
DOI: 10.1055/a-2272-8045
letter
Photoinduced Direct Carbamoylation of Ethers with Isocyanates towards the Synthesis of α-Amide-Substituted Ether Derivatives
The authors gratefully acknowledge the special funding support from the National Natural Science Foundation of China (22271266), the USTC–Yanchang Petroleum New Energy Joint Research Project (2022ZKD-02), the Fundamental Research Funds for the Central Universities (YD2340002001) and Students' Innovation and Entrepreneurship Foundation of the USTC (USTC, CY2022S01).
Abstract
Photoinduced carbamoylation of ethers using isocyanates as amide sources was accomplished under mild and environmentally friendly reaction conditions. A series of isocyanates were tolerated in this protocol to construct α-amide-substituted ether derivatives with desired yields. The method featured broad substrate scope and good functional group tolerance, which could play an important role in the construction of biological molecules with ethers.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2272-8045.
- Supporting Information
Publication History
Received: 04 December 2023
Accepted after revision: 20 February 2024
Accepted Manuscript online:
20 February 2024
Article published online:
11 March 2024
© 2024. Thieme. All rights reserved
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- 53 General Procedure for the Carbamoylation of Ethers with Isocyanate 1a A Schlenk tube was equipped with a magnetic stir bar and charged with isocyanate 1a (0.2 mmol, 1.0 equiv), tetrahydrofuran (1 mL), FeCl3 (5 mol%), and DTBP (2 equiv). The resulting mixture was sealed and degassed via vacuum evacuation and back-filled with nitrogen for three times after freezing using liquid nitrogen, and then irradiated with a 20 W 390 nm LED at room temperature for 24 h. After the reaction ended, the reaction solution was concentrated in vacuo and purified by silica gel column chromatography to give the desired product 3a with yield of 81%. 1H NMR (400 MHz, CDCl3): δ = 8.34 (s, 1 H), 7.38 (d, J = 8.3 Hz, 2 H), 7.05 (d, J = 8.1 Hz, 2 H), 4.38 (dd, J = 8.2, 6.0 Hz, 1 H), 4.06–3.74 (m, 2 H), 2.34–2.25 (m, 1 H), 2.24 (s, 3 H), 2.10 (td, J = 13.2, 6.3 Hz, 1 H), 1.94–1.77 (m, 2 H). 13C NMR (101 MHz, CDCl3): δ = 170.14, 133.71, 132.96, 128.47, 118.64, 77.62, 68.62, 29.17, 24.57, 19.85.