Nickel-Catalyzed Ligand-Free Hiyama Coupling of Aryl Bromides and Vinyltrimethoxysilane

Abstract

We herein disclose the first Ni-catalyzed Hiyama coupling of aryl halides with vinylsilanes. This protocol uses cheap, nontoxic, and stable vinyltrimethoxysilane as the vinyl donor, proceeds under mild and ligand-free conditions, furnishing a diverse variety of styrene derivatives in high yields with excellent functional group compatibility.

Keywords

nickel catalysis - vinylation - cross-coupling - Hiyama coupling - ligand-free conditions - vinylsilane - aryl halide

Publication History

Received: 30 November 2020

Accepted after revision: 31 January 2021

Accepted Manuscript online:
31 January 2021

Article published online:
16 February 2021

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• 27 General Procedure 1 In a nitrogen-filled glove box, aromatic halide (0.2 mmol, 1.0 equiv), 18-crown-6 (121.0 mg, 0.46 mmol, 2.3 equiv), KOMe (32.2 mg, 0.46 mmol, 2.3 equiv), NiCl₂(glyme) (4.4 mg, 0.02 mmol, 10 mol%), and DMF (1.0 mL) were charged to an 8 mL vial equipped with a magnetic stirrer bar. The vinyltrimethoxysilane (68.0 mg, 0.46 mmol, 2.3 equiv) was added. The vial was removed from the glove box, and the reaction mixture was stirred at rt (35 °C) for 12 h. The reaction mixture was then diluted with EtOAc and washed with water. The organic phase was dried over Na₂SO₄, filtered, and concentrated, and the residue was purified by column chromatography on silica gel to give the product. 2-Methoxy-6-vinylnaphthalene (3a) Using general procedure 1: white solid, 31.0 mg, yield: 84%. ¹H NMR (400 MHz, CDCl₃): δ = 7.78–7.66 (m, 3 H), 7.62 (dd, J = 8.7, 1.7 Hz, 1 H), 7.19–7.10 (m, 2 H), 6.87 (dd, J = 17.6, 10.9 Hz, 1 H), 5.84 (dd, J = 17.6, 0.9 Hz, 1 H), 5.30 (dd, J = 10.9, 0.9 Hz, 1 H), 3.93 (s, 3 H). General Procedure 2 In a nitrogen-filled glove box, aromatic halide (0.2 mmol, 1.0 equiv), TBAT (270 mg, 0.5 mmol, 2.5 equiv), NiCl₂(glyme) (4.4 mg, 0.02 mmol, 10 mol%), and DMA (1.0 mL) were charged to an 8 mL vial equipped with a magnetic stirrer bar. The vinyltrimethoxysilane (59.1 mg, 0.4 mmol, 2.0 equiv) was added. The vial was removed from the glove box, and the reaction mixture was stirred at rt (35 °C) for 12 h. The reaction mixture was then diluted with EtOAc and washed with water. The organic phase was dried over Na₂SO₄, filtered, and concentrated, and the residue was purified by column chromatography on silica gel to give the product. 2-Vinylnaphthalene (3b) Using general procedure 2: white solid, 25.5 mg, yield: 83%. ¹H NMR (400 MHz, CDCl₃): δ = 7.85–7.79 (m, 3 H), 7.76 (s, 1 H), 7.65 (dd, J = 8.6, 1.7 Hz, 1 H), 7.50–7.42 (m, 2 H), 6.90 (dd, J = 17.6, 10.9 Hz, 1 H), 5.89 (dd, J = 17.6, 0.8 Hz, 1 H), 5.35 (dd, J = 10.9, 0.8 Hz, 1 H).