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Synlett 2023; 34(17): 2029-2033
DOI: 10.1055/a-2102-7006
DOI: 10.1055/a-2102-7006
letter
Decarboxylative Oxidation of Carboxylic Acids Using Photocatalysis and Copper Catalysis
We thank Shanghai Jiao Tong University for financial support.
Abstract
A decarboxylative oxidation of carboxylic acids was developed through visible-light-induced photocatalysis with molecular oxygen as a green oxidant and copper as a co-catalyst. This reaction worked smoothly on various type of acids, and could potentially be used in modifications of natural products. The high efficiency of this transformation was demonstrated on over 40 substrates.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2102-7006.
- Supporting Information
Publication History
Received: 25 April 2023
Accepted after revision: 30 May 2023
Accepted Manuscript online:
30 May 2023
Article published online:
20 July 2023
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- 12 Photocatalytic Decarboxylation: General Procedure A 25 mL round-bottom flask equipped with a stirrer bar was charged with the appropriate substrate 1 (0.5 mmol, 1.0 equiv), [Ir(dF(CF3)ppy)2(dtbpy)]PF6 (16.9 mg, 3 mol%), CuO (7.9 mg, 20 mol%), bathophenanthroline (41 mg, 25mol%), and Cs2CO3(243 mg, 1.5 equiv). DCM (10 mL) was added, then the flask was quickly degassed three times and flushed with O2 from a balloon. The mixture was heated to 40 °C and irradiated with six 100 W blue LEDs (5 cm away) for 40 h. When the reaction was complete, the solvent was removed under a vacuum and the mixture was purified by flash chromatography (silica gel, PE–EtOAc). Benzyl 4-Oxopiperidine-1-carboxylate (2a) Prepared by the general procedure as a yellow liquid; yield: 99 mg (85%). IR (KBr): 2359, 1699, 1630, 1429, 1353 cm–1. 1H NMR (400 MHz, CDCl3): δ = 7.36–7.28 (m, 5 H), 5.15 (s, 2 H), 3.76 (t, J = 6.3 Hz, 4 H), 2.42 (t, J = 5.9 Hz, 4 H). 13C NMR (101 MHz, CDCl3): δ = 207.09, 155.05, 136.32, 128.54, 128.20, 127.99, 67.55, 43.07, 40.99. HRMS (ESI): m/z [M + Na]+ calcd for C13H15NNaO3: 256.0944; found: 256.0910. The spectra matched those reported in Ref. 10. 4-Fluorobenzaldehyde (2b) Prepared by the general procedure as a yellow liquid; yield: 45.5 mg (73%). IR (KBr): 1652, 1632, 1585, 1373, 1350 cm–1. 1H NMR (400 MHz, CDCl3): δ = 9.96 (s, 1 H), 7.96–7.85 (m, 2 H), 7.21 (t, J = 8.5 Hz, 2 H). MS (ESI): m/z = 147.1 [M + Na]+. The spectra matched those reported in Ref. 11.