Synthesis of 3-vinylpyrrole

New Boronic-Acid- and Boronate-Substituted Aromatic Compounds as Precursors of Fluoride-Responsive Conjugated Polymer Films

“…[16,17] 7 was prepared in 55% overall yield from pyrrole. [19,20] All these reagents exhibited physical characteristics similar to those reported in the literature. Ϫ For the synthesis of ''pinacol borane''-substituted compounds, the typical procedure was as follows: 5 mmol of the alkene was added dropwise to a well-stirred white suspension of Ipc 2 BH (1.70 g, 6.0 mmol) in anhydrous THF (8 mL) maintained at Ϫ40°C.…”

“…The same protocol was used for the vinyl derivative of the protected pyrrole 7, which was synthesized in four steps from pyrrole. [19,20] Deprotection of the functionalized pyrrole was carried out electrochemically at Ϫ2.45 V (vs. 10 Ϫ1  Ag ϩ /Ag) using pyrene as a redox mediator. Compared to the classical chemical deprotection method (i.e.…”

Regioselective Reduction of 2,4‐Diacylpyrroles and the Synthesis of a 2,4‐Divinylpyrrole

“…[11] The reduction of 2-and 3-acylpyrroles is generally carried out using sodium borohydride and 2-propanol or lithium aluminum hydride and ether, but the yields of the resulting carbinols are always low due to over reduction to give the corresponding alkylpyrroles. [3][4][5]7] We have found that using methanol as solvent for the reduction of diacylpyrrole 1, and the fractional addition of sodium borohydride at room temperature, produced a single product over a period of several hours. After work-up and chromatography on silica gel, 2-(1-hydroxyisobutyl)-4-isobutyryl)-1H-pyrrole (3) was obtained in 98 % yield (Scheme 2).…”

Five‐Membered Heterocycles: Pyrrole and Related Systems

“…Reduction of 3-acyl-1-(p-toluenesulfonyl)pyrroles with 0.5 equivalents of NaBH 4 in refluxing dioxane containing 1 equivalent of i-PrOH gives the corresponding intermediate 1-(pyrrol-3-yl)methanol derivatives, which undergo dehydration in hot DMSO, rendering 3-vinylpyrroles [570]. C-Vinylpyrroles are useful in various applications, for example cycloaddition reactions (Section 4.5.7), and comprehensive reviews highlighting the preparation [571] and synthetic uses of these compounds have appeared quite recently [572].…”