Palladium-Catalyzed Regiodivergent Decarboxylative Hydrothiocarbonylation of Vinylarenes Using Oxalic Acid Monothioesters

Kang Li; Ni Shen; Can Liu; Rui Shang

doi:10.1055/a-1807-8282

Synlett, Table of Contents

Synlett 2022; 33(08): 767-770
DOI: 10.1055/a-1807-8282

letter

Palladium-Catalyzed Regiodivergent Decarboxylative Hydrothiocarbonylation of Vinylarenes Using Oxalic Acid Monothioesters

Kang Li

^aDepartment of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China

,

Ni Shen

^aDepartment of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China

,

Can Liu

^aDepartment of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China

,

Rui Shang ∗

^aDepartment of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China

^bDepartment of Chemistry, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

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Abstract

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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 - regioselectivity

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References

References and Notes

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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.

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