Synlett 2013; 24(7): 873-877
DOI: 10.1055/s-0032-1318482
letter
© Georg Thieme Verlag Stuttgart · New York

Silver Ion Mediated In Situ Synthesis of Mixed Diaryl Sulfides from Diaryl Disulfides

Prasanta Gogoi
a  Department of Chemistry, National Institute of Technology, Silchar 788010, Assam, India   Fax: +91(3842)224797   Email: [email protected]
,
Sandhya R. Gogoi
b  Department of Chemical Science, Tezpur University, Tezpur 784028, Assam, India
,
Mukul Kalita
a  Department of Chemistry, National Institute of Technology, Silchar 788010, Assam, India   Fax: +91(3842)224797   Email: [email protected]
,
Pranjit Barman*
a  Department of Chemistry, National Institute of Technology, Silchar 788010, Assam, India   Fax: +91(3842)224797   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 11 February 2013

Accepted after revision: 26 February 2013

Publication Date:
15 March 2013 (online)


Abstract

The AgNO3-mediated in situ scission of aromatic disulfides in the presence of electron-rich aromatic compounds results in the efficient synthesis of diaryl sulfides. Key features of this new methodology are high yields of aromatic and heteroaromatic sulfides, mild reaction conditions, simplicity, simple workup, and avoiding foul-smelling reactants like thiols.

 
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    • 17b Synthesis of Aryl Benzyl Thioethers 4: Silver mercaptide (0.26 g, 1 mmol) and benzyl chloride (0.15 g, 1.2 mmol) in EtOH (5 mL) were refluxed for 6 h. Then NaOH (0.2 g, 5 mmol) was added and reflux continued for an additional 2 h. Upon cooling, NaOH (2 M, 30 mL) was added to the reaction mixture followed by extraction with CH2Cl2. The organic phase was washed with NaOH (2 M, 2 × 25 mL), H2O (25 mL) and brine (25 mL), dried over anhyd Na2SO4, filtered and the solvent removed under reduced pressure to give the aryl benzyl thioether. Representative Analytical Data; 1-(2-Nitrophenylthio)napthalen-2-ol (3f): The title compound was prepared according to the typical procedure in 75% yield (0.223 g) as a yellow solid (mp 170–171 °C). IR (KBr): 3435, 2905, 2845, 1588, 1545, 1497, 1335, 1055, 940, 865, 746, 689 cm–1. 1H NMR (400 MHz, CDCl3): δ = 8.27 (d, J = 7.9 Hz, 1 H), 8.16 (d, J = 8.6 Hz, 1 H), 7.86–7.97 (m, 6 H), 7.23 (s, 1 H), 6.84 (d, J = 7.6 Hz, 2 H). 13C NMR (100 MHz, CDCl3): δ = 161.2, 156.3, 155.3, 153.1, 148.6, 143.5, 138.4, 136.7, 130.2, 129.1, 128.5, 127.2, 118.6, 117.4, 115.0. HRMS (ESI): m/z [M + H+] calcd for C16H11NO3S: 298.0460; found: 298.0463. Anal. Calcd for C16H11NO3S: C, 64.63; H, 3.73; N, 4.71. Found: C, 64.58; H, 3.91; N, 4.88.
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