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Synlett 2022; 33(08): 767-770
DOI: 10.1055/a-1807-8282
DOI: 10.1055/a-1807-8282
letter
Palladium-Catalyzed Regiodivergent Decarboxylative Hydrothiocarbonylation of Vinylarenes Using Oxalic Acid Monothioesters
This work was financially supported by the National Natural Science Foundation of China (NSFC) and the University of Science and Technology of China (USTC, Grant Number GG 2065010002).
Abstract
Oxalic acid monothioester (OAM), an easily accessible and bench-stable reagent, is reported herein as a synthetic equivalent of thioester for palladium-catalyzed decarboxylative hydrothiocarbonylation of vinylarenes to achieve both branched and linear regioselectivity. The reactions provided user-friendly synthetic methods for preparation of α- or β-arylated propionic acid thioesters from vinylarenes without directly handling toxic carbon monoxide and odorous thiols.
Key words
oxalic acid monothioester - palladium - decarboxylative hydrothiocarbonylation - regioselectivitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1807-8282.
- Supporting Information
Publication History
Received: 22 February 2022
Accepted after revision: 24 March 2022
Accepted Manuscript online:
24 March 2022
Article published online:
22 April 2022
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- 16 General Procedure for Synthesis of 52-Vinyl naphthalene (1.0 equiv, 0.2 mmol), oxalic acid monothioester (1.5 equiv, 0.3 mmol), [Pd(allyl)Cl]2 (2 mol%, 1.5 mg), and (2-py)PPh2 (8 mol%, 4.3 mg) were placed in a 10 mL transparent Schlenk tube equipped with a stirring bar. The tube was evacuated and filled with argon (three times). To these solids, DCE (2.0 mL) was added via a gastight syringe under argon atmosphere. The mixture was stirred at 80 °C for 18 h. The mixture was quenched with brine and extracted with ethyl acetate (3 × 10 mL). The organic layers were combined and concentrated under vacuo. The product was purified by flash column chromatography on silica gel column (eluent: petroleum ether/ethyl acetate = 50:1) to afford 5 (55.2 mg, 90%); mp 95–97 °C. 1H NMR (400 MHz, CDCl3): δ = 7.88–7.81 (m, 4 H), 7.53–7.46 (m, 3 H), 7.24 (d, J = 8.1 Hz, 2 H), 7.19 (d, J = 8.3 Hz, 2 H), 4.18 (q, J = 7.0 Hz, 1 H), 2.36 (s, 3 H), 1.68 (d, J = 7.1 Hz, 3 H). 13C NMR (101 MHz, CDCl3): δ = 199.4, 139.5, 137.1, 134.4, 133.5, 132.8, 129.9, 128.5, 127.9, 127.7, 127.0, 126.2, 126.0, 125.9, 124.3, 54.1, 21.3, 18.7.