Cu–iminopyridine complexes as catalysts for carbene and nitrene transfer reactions. (21st May 2014)

• Record Type: Journal Article
• Authors: Abedi, Yaghoub; Biffis, Andrea; Gava, Riccardo; Tubaro, Cristina; Chelucci, Giorgio; Stoccoro, Sergio
• Is Part Of: Applied organometallic chemistry. Volume 28:Number 7(2014:Jul.)
• Page Start: 512
• Page End: 516
• Publication Date: 2014-05-21
• Subjects: Organometallic chemistry -- Periodicals; Organometallic compounds -- Periodicals; 547.05
• DOI: 10.1002/aoc.3155
• Languages: English
• ISSNs: 0268-2605

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Copper complexes with chiral iminopyridine ligands were screened for their catalytic efficiency in carbene (<named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">cyclopropanation</named-content>) and nitrene transfer reactions (<named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">aziridination</named-content>, CH <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">amidation</named-content>). Both pre‐formed and <italic>in situ</italic> formed complexes were considered. The results highlighted the poor catalytic efficiency of these complexes in <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">cyclopropanation reactions</named-content> employing methyl phenyldiazoacetate as the carbene source, whereas better results were obtained in nitrene transfer reactions, particularly in the <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">amidation</named-content> of CH bonds, albeit the <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">enantioselectivity</named-content> of the reactions was negligible in nearly all cases. Finally, copper complexes were also found to promote an interesting oxidative <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">functionalization</named-content> of alkynes with PhI(OAc)<sub>2</sub> at room temperature. Copyright © 2014 John Wiley & Sons, Ltd.</p> </abstract>