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Synlett 2017; 28(07): 841-846
DOI: 10.1055/s-0036-1588135
DOI: 10.1055/s-0036-1588135
letter
Transition-Metal-Free C–N Bond Activation: Synthesis of α,α-Bis(arylthio) Aldehydes
Further Information
Publication History
Received: 01 November 2016
Accepted after revision: 13 December 2016
Publication Date:
07 March 2017 (online)
Abstract
A novel and convenient tandem reaction of I2-catalzyed C–N bond activation of tertiary amines and subsequent aryl thiolation has been explored. A variety of disulfides and series of tertiary amines were efficiently converted into the corresponding α,α-bis(arylthio) aldehydes in moderate to good yields. The reaction proceeded well under transition-metal-free conditions via a C–N activation process.
Key words
disulfides - transition-metal-free - α,α-bis(arylthio) aldehydes - tertiary amine - radicalsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588135.
- Supporting Information
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- 17 Typical Procedure Under air atmosphere, a reaction tube was charged with disulfane (0.2 mmol), tertiary amine (0.4 mmol), I2 (0.4 mmol), Na2CO3 (0.4 mmol), and DMSO (2 mL). The vessel was sealed and heated at 100 °C (oil bath temperature) for 24 h and then cooled to r.t. The reaction mixture was washed with sat. Na2S2O3 (2 × 15 mL) and then brine (1 × 15 mL). After the aqueous layer was extracted with EtOAc, the combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography (hexane–EtOAc) to afford the desired products 3. 2,2-Bis(phenylthio)acetaldehyde (3) Yellow oil (41.6 mg, 80% yield). 1H NMR (500 MHz, CDCl3): δ = 9.28 (d, J = 4.5 Hz, 1 H), 7.48 (dd, J = 6.6, 2.9 Hz, 4 H), 7.34–7.32 (m, 6 H), 4.72 (d, J = 4.5 Hz, 1 H). 13C NMR (125 MHz, CDCl3): δ = 189.4, 133.6, 130.9, 129.3, 128.9, 62.0. IR (ATR): ν = 3015, 2976, 1717, 1539, 1469, 1362, 1230, 1025, 737, 689 cm–1. ESI-HRMS: m/z calcd for C14H12NaOS2 + [M + Na]+: 283.0222; found: 283.0216.