Metal -free PhI(OAc)2-oxidized decarboxylation of propiolic acids towards synthesis of α-acetoxy ketones and insights into general decarboxylation with DFT calculations.
Org Biomol Chem
; 21(7): 1457-1462, 2023 Feb 15.
Article
em En
| MEDLINE
| ID: mdl-36651659
ABSTRACT
A metal-free oxidative decarboxylation reaction of propiolic acids mediated by hypervalent iodine(III) reagents is described. This decarboxylative C-O bond-forming reaction used a combination of (diacetoxyiodo)benzene and aromatic, heteroaromatic or aliphatic propiolic acids to give the corresponding α-acetoxy ketones. Preliminary mechanistic studies based on both DFT calculations and high-resolution mass spectroscopy (HRMS) suggested that the reaction proceeded through decarboxylation to form a propargyl iodide intermediate. This reaction provides an attractive alternative to existing methods for the exclusive synthesis of α-acyloxy ketones.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Org Biomol Chem
Assunto da revista:
BIOQUIMICA
/
QUIMICA
Ano de publicação:
2023
Tipo de documento:
Article
País de afiliação:
China