Semipinacol Rearrangement of Iododifluorohomoallyl Alcohols and Its Application in the Allylic C-H Esterification Reactions.
J Org Chem
; 89(5): 3111-3122, 2024 Mar 01.
Article
em En
| MEDLINE
| ID: mdl-38343173
ABSTRACT
We herein present a study on the Ag(I)-mediated semipinacol rearrangement of iododifluorohomoallyl alcohols, the resulting allylic difluoromethyl ketones underwent oxidative allylic C-H esterification under palladium catalysis in the absence of external ligand. This process yielded a range of difluoromethyl ketones derived from allyl esters in a single operation. The reaction features broad scope of o-nitrobenzoic acids and homoallylic iododifluoroalcohols affording the targeted molecules in synthetically useful yields. Control experiments illustrated that the silver salt acted as not only a Lewis acid to promote the cleavage of a C-I bond and furnish the semipinacol rearrangement but also a co-oxidant in the catalytic cycle for the allylic C-H esterification.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
China