Stereoselective Aromatic O-Glycosylation of Glycosyl Chloride with Arylboronic Acid under an Air Atmosphere.
J Org Chem
; 88(15): 10721-10734, 2023 Aug 04.
Article
in En
| MEDLINE
| ID: mdl-37488471
ABSTRACT
A novel exclusive ß-selective O-aryl glycosylation was developed using glycosyl chloride and arylboronic acid with a palladium catalyst under an air atmosphere. The reaction was insensitive to moisture and characterized using readily available and bench-stable glycosyl chloride and arylboronic acid as substrates. A diverse range of substrate scopes, including various arylboronic acids and glycosyl chloride donors, was well-tolerated in this method. Arylboronic acid was oxidized by O2 in air to produce phenol as the aromatic source. This new strategy provides an alternative route and may find broad applications in efficient synthesis of bioactive O-aryl glycosides in the future.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
J Org Chem
Year:
2023
Document type:
Article