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Synlett 2015; 26(07): 915-920
DOI: 10.1055/s-0034-1380125
DOI: 10.1055/s-0034-1380125
letter
Facile Approach for C(sp3)–H Bond Thioetherification of Isochroman
Further Information
Publication History
Received: 22 November 2014
Accepted after revision: 05 January 2015
Publication Date:
10 February 2015 (online)
![](https://www.thieme-connect.de/media/synlett/201507/lookinside/thumbnails/10.1055-s-0034-1380125-1.jpg)
Abstract
An unprecedented C–S formation protocol via the direct oxidative C(sp3)–H bond thioesterification of isochroman under metal-free conditions was developed. A series of isochroman derivatives could be afforded efficiently by the green, simple, and atom-economical method.
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- 16 General Procedure for the Oxidative C–S Formation A sealed tube was charged with isochroman (or benzylic ether; 1 mmol), DTBP (1.5 mmol), thiol (or thiophenol; 1.5 mmol). The reaction mixture was stirred at 120 °C for 6 h. The reaction mixture was then cooled to obtain a brown liquid. The organic solutions could be purified directly by column chromatography on silica gel to give the pure product (hexane–EtOAc, 20:1). 1-[(4-Chlorophenyl)thio]isochromane 3a Colorless oil; yield: 212 mg (77%). 1H NMR (500 MHz, CDCl3): δ = 7.56 (d, J = 8.3 Hz, 2 H), 7.40–7.30 (m, 3 H), 7.28–7.21 (m, 2 H), 7.20–7.11 (m, 1 H), 6.49 (s, 1 H), 4.55 (td, J = 11.5, 3.3 Hz, 1 H), 4.03 (dd, J = 11.3, 6.2 Hz, 1 H), 3.20–3.09 (m, 1 H), 2.72 (dd, J = 16.5, 2.4 Hz, 1 H). 13C NMR (126 MHz, CDCl3): δ = 133.56, 132.90, 132.48, 132.27, 131.64, 128.06, 127.89, 126.93, 126.13, 125.16, 85.06, 76.39, 76.14, 75.89, 57.36, 26.75. Anal. Calcd for C15H13ClOS: C, 65.09; H, 4.73. Found: C, 64.88; H, 4.64. ESI-MS: m/z = 276.
For selected reviews or books on transition-metal-catalyzed C–H functionalization, see:
For selected reviews on C(sp)–H or C(sp2)–H bond functionalization via CDC protocols, see:
For selected reviews on C(sp3)–H bond functionalization involving CDC protocols, see:
For selected references, see:
For selected references, see:
For selected examples, see:
For selected references, see:
For selected C–C bond formations at the C(1) position of isochroman examples, see:
For selected references, see: