Access to 5-fluoroalkylated trisubstituted oxazoles

Amides Catalysis Copper Cyclization Oxazoles

Journal

Chemical communications (Cambridge, England)
ISSN: 1364-548X
Titre abrégé: Chem Commun (Camb)
Pays: England
ID NLM: 9610838

Informations de publication

Date de publication:
14 Apr 2022
Historique:
pubmed: 30 3 2022
medline: 16 4 2022
entrez: 29 3 2022
Statut: epublish

Résumé

A novel copper-catalyzed cyclization of α-fluoroalkyl-α-diazoketones with (thio)amides has been developed. This mechanistically distinct protocol provides a robust and straightforward approach to construct 5-fluoroalkylated trisubstituted oxazoles and thiazoles with high efficiency and excellent functional group compatibility. Experimental studies suggest a mechanism involving imidate ligand migratory insertion of a copper carbenoid as the key step.

Identifiants

DOI: 10.1039/d2cc01057g PMID: 35348157
pubmed: 35348157
doi: 10.1039/d2cc01057g
doi:

Substances chimiques

Amides 0
Oxazoles 0
Copper 789U1901C5

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

4853-4856

Auteurs

Di Jiang (D)

State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China. nklibin@nankai.edu.cn.

Jingpei Jia (J)

State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China. nklibin@nankai.edu.cn.

Baiquan Wang (B)

State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China. nklibin@nankai.edu.cn.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
ORCID: 0000-0003-4605-1607

Bin Li (B)

State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China. nklibin@nankai.edu.cn.
ORCID: 0000-0003-3909-3796

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Classifications MeSH

questionsmedicales.fr › Composés chimiques organiques › Amides › Access to 5-fluoroalkylated trisubstituted oxazoles
questionsmedicales.fr › Phénomènes chimiques › Catalyse › Access to 5-fluoroalkylated trisubstituted oxazoles
questionsmedicales.fr › Produits chimiques inorganiques › Métaux › Métaux lourds › Cuivre › Access to 5-fluoroalkylated trisubstituted oxazoles
questionsmedicales.fr › Métabolisme › Cyclisation › Access to 5-fluoroalkylated trisubstituted oxazoles
questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Azoles › Oxazoles › Access to 5-fluoroalkylated trisubstituted oxazoles