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Synlett 2024; 35(03): 325-329
DOI: 10.1055/a-2153-6687
DOI: 10.1055/a-2153-6687
cluster
Organic Chemistry Under Visible Light: Photolytic and Photocatalytic Organic Transformations
Visible-Light-Promoted Synthesis of Vinyloxaziridines from Conjugated Carbonyls
This material is based upon work supported by the National Science Foundation CAREER and MRI awards: CHE-1752085 and CHE-1827938.
Abstract
We report the first visible-light-promoted synthesis of vinyloxaziridines from simple conjugated nitrones. We have found that vinyl nitrones formed by the condensation reaction between conjugated carbonyls and hydroxylamines undergo visible-light-promoted energy-transfer isomerization to the respective vinyloxaziridines in very high yields and selectivities. The reaction scope expands to a large array of substitution patterns, and evidence indicates that the proposed energy-transfer pathway is the predominant mechanism for this transformation.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2153-6687.
- Supporting Information
Publication History
Received: 31 May 2023
Accepted after revision: 14 August 2023
Accepted Manuscript online:
14 August 2023
Article published online:
28 September 2023
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- 21 General protocol for synthesis of vinyloxaziridines from vinylnitrones: A 50 mL round-bottomed flask equipped with a magnetic stirrer was charged with benzene (20 mL) and the appropriate vinyl nitrone (1 mmol, 1 equiv). The mixture was exposed to a white LED, and the reaction was monitored by TLC. The resulting mixture was purified by chromatography (silica gel). 2-Benzyl-3-[(E)-2-phenylvinyl]oxaziridine (2d): Prepared from nitrone 1d (0.1 mmol) by the general protocol and purified by automated flash chromatography [silica gel (10 g cartridge), heptanes–EtOAc (20:1 to 1:1, 14 mL/min, 12 min)] as a clear oil; yield: 23 mg (98%); TLC: Rf 0.58 (heptanes–EtOAc, 3:1). IR (thin film) 3104, 3041, 2992, 1654, 1520, 1498, 1464, 1281, 1201 cm–1. 1H NMR (400 MHz, CDCl3): δ = 7.47–7.32 (m, 10 H), 7.01 (d, J = 16.0 Hz, 1 H), 5.98 (dd, J = 16.0, 7.1 Hz, 1 H), 4.40 (d, J = 7.1 Hz, 1 H), 4.06 (d, J = 8.0 Hz, 1 H), 3.90 (d, J = 8.0 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ = 138.5, 135.3, 135.2, 128.9, 128.8, 128.7, 128.6, 127.9, 126.9, 124.2, 80.9, 65.5. ESI-MS: m/z (%): (pos.) 238.1 ([M + H]+, 100); (neg) 236.1 ([M – H]–, 100). HRMS (ESI): m/z [M + H]+ calcd for C16H16NO: 238.30945; found: 238.30968. Absolute difference: 0.96 ppm.