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Synlett 2018; 29(10): 1340-1345
DOI: 10.1055/s-0037-1609443
DOI: 10.1055/s-0037-1609443
letter
Visible-Light-Promoted Difunctionalization of Olefins Leading to α-Thiocyanato Ketones
Authors
This work was supported by the Opening Project of Key Laboratory at Universities of Education Department of Xinjiang Uygur Autonomous Region (No. 2017YSHXZD04).
Further Information
Publication History
Received: 07 January 2018
Accepted after revision: 08 March 2018
Publication Date:
23 April 2018 (online)
Abstract
A simple and convenient visible-light-induced difunctionalization of alkenes with ammonium thiocyanate and dioxygen has been developed at room temperature. A series of α-thiocyanato ketones could be easily and efficiently obtained in moderate to good yields through the formation of C–S and C=O bonds simply by using nontoxic and inexpensive Na2-Eosin Y as a photocatalyst.
Key words
visible-light catalysis - difunctionalization - alkenes - ammonium thiocyanate - α-thiocyanato ketonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609443.
- Supporting Information (PDF)
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- 16 Preparation of 1-Phenyl-2-thiocyanatoethanone (4a) To a solution of NH4SCN (2) (30.4 mg, 0.4 mmol) and Na2-EosinY (2.8 mg, 0.004 mmol, 2 mol%) in CH3CN (5 mL) was added alkene 1a (20.8 mg, 0.2 mmol). The reaction mixture was stirred under the irradiation of 3W blue LED under an oxygen atmosphere at r.t. for 5 h. After completion of the reaction, the solution was concentrated under vacuum. The residue was purified by using a mixture of ethyl acetate and petroleum ether (1:10) as eluent to give the desired product 4a. Yield: 30 mg (79%). 1H NMR (CDCl3, 500 MHz, ppm): δ = 7.95 (d, J = 8.0 Hz, 2 H), 7.68 (t, J = 7.3 Hz, 1 H), 7.54 (t, J = 7.7 Hz, 2 H), 4.75 (s, 2 H). 13C NMR (CDCl3, 125 MHz, ppm): δ = 190.8, 134.8, 134.0, 129.2, 128.5, 111.9, 43.0. HRMS: m/z [M + Na]+ calcd for C9H7NOSNa: 200.0146; found 200.0149.
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