Methylene C(sp3)–H β,β′-Diarylation of Cyclohexanecarbaldehydes Promoted by a Transient Directing Group and Pyridone Ligand

Autor:	Andrew J. P. White, Sahra St John-Campbell, James A. Bull
Přispěvatelé:	The Royal Society, Engineering & Physical Science Research Council (EPSRC)
Rok vydání:	2020
Předmět:	Cyclohexane Chemistry Ligand Aryl Organic Chemistry Biochemistry Medicinal chemistry Enamine chemistry.chemical_compound Yield (chemistry) Amide Reactivity (chemistry) Physical and Theoretical Chemistry Methylene 03 Chemical Sciences
Zdroj:	Organic Letters. 22:1807-1812
ISSN:	1523-7052 1523-7060
Popis:	A hindered β-amino amide transient directing group effects di-trans-arylation of cyclohexanecarbaldehydes. The amide N-substituents are shown to affect yield and can enhance the rate of arylation compared with the α-amino acid. Addition of a pyridone ligand further enhanced reactivity. The reaction is successful for a range of aryl iodides, and various substituted cyclohexane carboxaldehydes, providing functionalized products from simple feedstocks. A mechanism is proposed evoking a transient enamine.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::34a5897cfc8d23ca020afb2698e9a719 https://doi.org/10.1021/acs.orglett.0c00124 Zobrazit plný text záznamu