Nickel(ii)-catalyzed reductive silylation of alkenyl methyl ethers for the synthesis of alkyl silanes

Abstract

A Ni(ii)-catalyzed tandem reaction including vinyl C–O bond silylation and olefin hydrogenation has been developed providing structurally diversified alkyl silanes.

Photo-Triggered, Copper(II) Chloride-Catalyzed Radical Hydroalkylation and Hydrosilylation of Vinylboronic Esters To Access Alkylboronic Esters

“…Compound 30 has been previously reported. 31 1 H NMR (600 MHz, CDCl 3 ) δ 7.34−7.29 (m, 1H), 6.31−6.27 (m, 1H), 6.00 (d, J = 3.1 Hz, 1H), 2.68−2.63 (m, 2H), 0.97 (t, J = 8.0 Hz, 9H), 0.95−0.91 (m, 2H), 0.56 (q, J = 8.0 Hz, 6H). 13 C{ 1 H} NMR (151 MHz, CDCl 3 ) δ: 158.8, 140.6, 110.2, 103.9, 22.5, 9.7, 7.5, 3.3.…”

“…Triethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)silane (31). To a 25 mL oven-dried Schlenk tube containing a magnetic stir bar were added product 12 (135 mg, 0.5 mmol, 1 equiv), chloroiodomethane (106 mg, 0.6 mmol, 1.2 equiv), and THF (5.0 mL) were added.…”

“…The crude residue was purified by flash column chromatography (SiO 2 ; PE) to afford 30 as a colorless oil (0.5 mmol scale: 87.3 mg, 83%). Compound 30 has been previously reported …”