Nickel-Catalyzed Reductive Cross-Coupling of Benzylic Sulfonium Salts with Aryl Iodides

Wei Wang; Ken Yao; Fan Wu

doi:10.1055/s-0041-1737762

Synlett, Inhaltsverzeichnis

Synlett 2022; 33(04): 361-366
DOI: 10.1055/s-0041-1737762

letter

Nickel-Catalyzed Reductive Cross-Coupling of Benzylic Sulfonium Salts with Aryl Iodides

Wei Wang

^aCenter for Supramolecular Chemistry and Catalysis and Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444

,

Ken Yao

^aCenter for Supramolecular Chemistry and Catalysis and Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444

,

Fan Wu∗

^bInstitute of Drug Discovery Technology and Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China

› Institutsangaben

Abstract

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Abstract

A nickel-catalyzed cross-electrophile coupling of benzylic sulfonium salts with aryl iodides has been developed, providing direct access to diarylalkanes from readily available and stable coupling partners. Preliminary mechanistic studies suggest that the C–S bond cleavage proceeds through a single-electron transfer process to generate a benzylic radical.

Key words

nickel catalysis - cross-coupling - arylation - diarylalkanes - sulfonium salts - aryl iodides

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Referenzen

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23 Methyl 4-(3,4,5-Trimethoxybenzyl)benzoate (11); Scaled-Up Synthesis A flame-dried Schlenk flask was charged with dimethyl(3,4,5-trimethoxybenzyl)sulfonium triflate (863 mg, 2.2 mmol, 110 mol%), methyl 4-iodobenzoate (2; 524 mg, 2.0 mmol, 100 mol%), Ni(acac)₂ (51 mg, 0.2 mmol, 10 mol%), 4,4′-di-tert-butyl-2,2′-bipyridine (81 mg, 0.3 mmol, 15 mol%), Zn powder (392 mg, 6.0 mmol, 200 mol%), and MgCl₂ (190 mg, 2.0 mmol, 100 mol%). The tube was capped with a rubber septum and evacuated and refilled with N₂ three times. DMA (1.0 mL) was then added to the flask from a syringe, and the mixture was stirred at r.t. for 12 h under N₂. The reaction was then quenched with H₂O and the mixture was diluted with EtOAc (100 mL). The organic layer was washed with H₂O (2 × 50 mL), dried (Na₂SO₄), filtered, and evaporated under reduced pressure. The residue was purified by column chromatography [silica gel, 3% EtOAc in PE] to give a colorless oil; yield: 546 mg (86%). ¹H NMR (600 MHz, CDCl₃): δ = 7.97 (d, J = 8.3 Hz, 2 H), 7.27 (d, J = 8.3 Hz, 2 H), 6.38 (s, 2 H), 3.97 (s, 2 H), 3.90 (s, 3 H), 3.83 (s, 3 H), 3.80 (s, 6 H). ¹³C NMR (151 MHz, CDCl₃): δ = 167.0, 153.3, 146.2, 136.5, 135.7, 129.8, 128.8, 128.2, 106.0, 60.8, 56.0, 52.0, 42.1. HRMS (ESI): m/z [M + Na]⁺ calcd for C₁₈H₂₀NaO₅: 339.1203; found: 339.1190.
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Zusatzmaterial

Supporting Information