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

Jianbo Zhang, Sehoon Park*, Sukbok Chang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Described herein is the selective reduction of sugars with hydrosilanes catalyzed by using Piers’ borane [(C6F5)2BH] generated in situ. The hydrosilylative C−O bond cleavage of silyl-protected mono- and disaccharides in the presence of a (C6F5)2BH catalyst, generated in situ from (C6F5)2BOH, 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.

Original languageEnglish
Pages (from-to)13757-13761
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number44
DOIs
StatePublished - 23 Oct 2017
Externally publishedYes

Keywords

  • bond cleavage
  • chemoselectivity
  • hydrosilylative reduction
  • Piers’ borane
  • sugars

Fingerprint Dive into the research topics of 'Selective C−O Bond Cleavage of Sugars with Hydrosilanes Catalyzed by Piers’ Borane Generated In Situ'. Together they form a unique fingerprint.

Cite this