Inhibition of (dppf)nickel-catalysed Suzuki–Miyaura cross-coupling reactions by α-halo-N-heterocycles†

Autor:	Alasdair K. Cooper, Megan Greaves, Alan R. Kennedy, William Donohoe, Thomas O. Ronson, David J. Nelson, Paul M. Burton
Jazyk:	angličtina
Rok vydání:	2021
Předmět:	Transmetalation Nickel Chemistry chemistry Reagent Polymer chemistry chemistry.chemical_element QD General Chemistry Medicinal chemistry Oxidative addition Coupling reaction Catalysis
Zdroj:	Chemical Science
ISSN:	2041-6539 2041-6520
Popis:	A nickel/dppf catalyst system was found to successfully achieve the Suzuki–Miyaura cross-coupling reactions of 3- and 4-chloropyridine and of 6-chloroquinoline but not of 2-chloropyridine or of other α-halo-N-heterocycles. Further investigations revealed that chloropyridines undergo rapid oxidative addition to [Ni(COD)(dppf)] but that α-halo-N-heterocycles lead to the formation of stable dimeric nickel species that are catalytically inactive in Suzuki–Miyaura cross-coupling reactions. However, the corresponding Kumada–Tamao–Corriu reactions all proceed readily, which is attributed to more rapid transmetalation of Grignard reagents. Nickel complexes with a dppf ligand can form inactive dinickel(ii) complexes during Suzuki–Miyaura cross-coupling reactions. However, these complexes can react with Grignard reagents in Kumada–Tamao–Corriu cross-coupling reactions.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2de88e5dd944fd3bd521e29fa1349a3e http://europepmc.org/articles/PMC8565371 Zobrazit plný text záznamu