Selective C-O Bond Cleavage of Sugars with Hydrosilanes Catalyzed by Piers' Borane Generated In Situ

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Described herein is the selective reduction of sugars with hydrosilanes catalyzed by using Piers' borane [(C6F5)(2)BH] generated in situ. The hydrosilylative C-O bond cleavage of silyl-protected mono-and disaccharides in the presence of a (C6F5)(2)BH catalyst, generated in situ from (C6F5)(2)BOH, takes place with excellent chemo- and regioselectivities to provide a range of polyols. A study of the substituent effects of sugars on the catalytic activity and selectivity revealed that the steric environment around the anomeric carbon (C1) is crucial.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2017-10
Language
English
Article Type
Article
Keywords

BIS(PENTAFLUOROPHENYL)BORINIC ACID; B(C6F5)(3)-CATALYZED HYDROSILATION; HYDROSILYLATION CATALYSTS; ALKENE HYDROSILYLATION; TERTIARY SILANES; ALKYL ETHERS; H-H; REDUCTION; HYDROGENATION; DEOXYGENATION

Citation

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.56, no.44, pp.13757 - 13761

ISSN
1433-7851
DOI
10.1002/anie.201708109
URI
http://hdl.handle.net/10203/227209
Appears in Collection
CH-Journal Papers(저널논문)
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