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Title: Palladium( ii )-assisted activation of thioglycosides
Described herein is the first example of glycosidation of thioglycosides in the presence of palladium( ii ) bromide. While the activation with PdBr 2 alone was proven feasible, higher yields and cleaner reactions were achieved when these glycosylations were performed in the presence of propargyl bromide as an additive. Preliminary mechanistic studies suggest that propargyl bromide assists the reaction by creating an ionizing complex, which accelerates the leaving group departure. A variety of thioglycoside donors in reactions with different glycosyl acceptors were investigated to determine the initial scope of this new reaction. Selective and chemoselective activation of thioglycosides over other leaving groups has also been explored.  more » « less
Award ID(s):
1800350
NSF-PAR ID:
10276724
Author(s) / Creator(s):
; ;
Date Published:
Journal Name:
Organic & Biomolecular Chemistry
Volume:
19
Issue:
9
ISSN:
1477-0520
Page Range / eLocation ID:
2044 to 2054
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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