A highly selective synthesis of 1‐substituted (E)‐buta‐1,3‐dienes with 4,4,5,5‐tetramethyl‐2‐vinyl‐1,3,2‐dioxaborolane as building block |
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| Authors: | Justyna Szudkowska‐Fr?tczak Aline Ryba Adrian Franczyk J?drzej Walkowiak Maciej Kubicki Piotr Pawlu? |
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| Institution: | 1. Faculty of Chemistry, Adam Mickiewicz University, Poznan, Poland;2. Center of Advanced Technologies, Adam Mickiewicz University, Poznan, Poland |
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| Abstract: | Highly selective synthesis of 1‐substituted (E)‐buta‐1,3‐dienes via palladium‐catalyzed Suzuki–Miyaura cross‐coupling of (E)‐alkenyl iodides with 4,4,5,5‐tetramethyl‐2‐vinyl‐1,3,2‐dioxaborolane ( 1 ) is reported. The vinylboronate pinacol ester ( 1 ) acts as a vinyl building block to show high chemoselectivity for the Suzuki–Miyaura pathway versus Heck coupling in the presence of biphasic conditions (Pd(PPh3)4, aqueous K2CO3, toluene and ethanol). Copyright © 2014 John Wiley & Sons, Ltd. |
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| Keywords: | cross‐coupling palladium(0) vinylboronate ester buta‐1 3‐dienes Suzuki– Miyaura coupling |
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