A robust and tunable halogen bond organocatalyzed 2-deoxyglycosylation involving quantum tunneling

Xu C, Bhaskara Rao VU, Weigen J, Loh CCJ.  (2020) Nat Commun

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The Loh's research group developed a robust, tunable, mild and anomeric selective halogen bond (XB) catalyzed 2-deoxyglycosylation that tolerates a broad range of glycosyl substrates.

Mechanistic investigations unveiled an intricate switchable reaction network modulated by XB interactions and suggests that quantum tunneling is involved in the rate determining step. Benchmarking studies against conventional thiourea catalysis revealed broadly superior performances using a monodentate halo-benzimidazolium XB catalyst.