Amine‐bridged bis(phenol) ligands for efficient Pd‐catalyzed aqueous C‐C coupling reactions. (27th August 2013)

• Record Type: Journal Article
• Authors: Zhou, Zhonggao; Liu, Minyan; Wu, Xiaoli; Yu, Hongwei; Xu, Guohai; Xie, Yongrong
• Is Part Of: Applied organometallic chemistry. Volume 27:Number 10(2013:Oct.)
• Page Start: 562
• Page End: 569
• Publication Date: 2013-08-27
• Subjects: Organometallic chemistry -- Periodicals; Organometallic compounds -- Periodicals; 547.05
• DOI: 10.1002/aoc.3033
• Languages: English
• ISSNs: 0268-2605

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>The influence of ring size (<bold>5</bold> or <bold>6</bold>), chain length (<bold>1</bold>, <bold>2</bold> or <bold>3</bold>) and bulkiness of <italic>N</italic>‐aryl substituents in amine‐bridged bis(phenol) ligands (<bold>1</bold>, <bold>2</bold>, <bold>3</bold>) on palladium‐catalyzed aqueous <named-content id="d359e1098" content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">C‐C coupling reactions</named-content> were revealed. The <named-content id="d359e1101" content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">homocoupling</named-content> of arylboronic acid can be completed in neat water with the aid of a catalytic amount of <italic>p</italic>‐toluenesulfonyl chloride (TsCl) in a very short time under anaerobic or aerobic conditions. Interestingly, the same catalytic system was efficient for <named-content id="d359e1109" content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">Suzuki–Miyaura reaction</named-content> in aqueous acetone under aerobic conditions in the absence of TsCl. The crystal structures of ligand 1 and three unsymmetrical fluorine‐substituted biaryl derivatives were also reported. Copyright © 2013 John Wiley &amp; Sons, Ltd.</p> </abstract>