On November 23, 2023, the team of Prof. Niu
Dawen from the State Key Laboratory of Biotherapy, West China Hospital and
School of Chemical Engineering of Sichuan University published a research
article entitled "Palladium catalysis enables cross-coupling-like SN2-
glycosylation of phenols" in Science.
Here is the abstract:
Despite their importance in life and
material sciences, the efficient construction of stereo-defined glycosides
remains a challenge.
Studies of carbohydrate functions would be
advanced if glycosylation methods were as reliable and modular as palladium
(Pd)-catalyzed cross-coupling. However, Pd-catalysis excels in forming
sp2-hybridized carbon centers whereas glycosylation mostly builds
sp3-hybridized C–O linkages. We report a glycosylation platform through
Pd-catalyzed SN2 displacement from phenols toward bench-stable,
aryl-iodide–containing glycosyl sulfides. The key Pd(II) oxidative addition
intermediate diverges from an arylating agent (Csp2 electrophile) to a
glycosylating agent (Csp3 electrophile). This method inherits many merits of
cross-coupling reactions, including operational simplicity and functional group
tolerance. It preserves the SN2 mechanism for various substrates and is
amenable to late-stage glycosylation of commercial drugs and natural products.
