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. (29th January 2014)

• Record Type: Journal Article
• Authors: Szudkowska‐Frątczak, Justyna; Ryba, Aline; Franczyk, Adrian; Walkowiak, Jędrzej; Kubicki, Maciej; Pawluć, Piotr
• Is Part Of: Applied organometallic chemistry. Volume 28:Number 3(2014:Mar.)
• Page Start: 137
• Page End: 139
• Publication Date: 2014-01-29
• Subjects: Organometallic chemistry -- Periodicals; Organometallic compounds -- Periodicals; 547.05
• DOI: 10.1002/aoc.3095
• Languages: English
• ISSNs: 0268-2605

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Highly selective synthesis of 1‐substituted (<italic>E</italic>)‐buta‐1, 3‐dienes via palladium‐catalyzed <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">Suzuki–Miyaura cross‐coupling</named-content> of (<italic>E</italic>)‐alkenyl iodides with 4, 4, 5, 5‐tetramethyl‐2‐vinyl‐1, 3, 2‐dioxaborolane (<bold>1</bold>) is reported. The vinylboronate pinacol ester (<bold>1</bold>) acts as a vinyl building block to show high chemoselectivity for the <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">Suzuki–Miyaura</named-content> pathway versus <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">Heck coupling</named-content> in the presence of biphasic conditions (Pd(PPh₃)₄, aqueous K₂CO₃, toluene and ethanol). Copyright © 2014 John Wiley &amp; Sons, Ltd.</p> </abstract>