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

Jianbo Zhang; Sehoon Park; Sukbok Chang

doi:10.1002/anie.201708109

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 journal › Article › peer-review

30 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 language	English
Pages (from-to)	13757-13761
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	44
DOIs	https://doi.org/10.1002/anie.201708109
State	Published - 23 Oct 2017
Externally published	Yes

Keywords

Piers’ borane
bond cleavage
chemoselectivity
hydrosilylative reduction
sugars

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10.1002/anie.201708109

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title = "Selective C−O Bond Cleavage of Sugars with Hydrosilanes Catalyzed by Piers{\textquoteright} Borane Generated In Situ",

abstract = "Described herein is the selective reduction of sugars with hydrosilanes catalyzed by using Piers{\textquoteright} 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.",

keywords = "Piers{\textquoteright} borane, bond cleavage, chemoselectivity, hydrosilylative reduction, sugars",

author = "Jianbo Zhang and Sehoon Park and Sukbok Chang",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

month = oct,

day = "23",

doi = "10.1002/anie.201708109",

language = "英语",

volume = "56",

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journal = "Angewandte Chemie - International Edition",

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T1 - Selective C−O Bond Cleavage of Sugars with Hydrosilanes Catalyzed by Piers’ Borane Generated In Situ

AU - Zhang, Jianbo

AU - Park, Sehoon

AU - Chang, Sukbok

PY - 2017/10/23

Y1 - 2017/10/23

N2 - 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.

AB - 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.

KW - Piers’ borane

KW - bond cleavage

KW - chemoselectivity

KW - hydrosilylative reduction

KW - sugars

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U2 - 10.1002/anie.201708109

DO - 10.1002/anie.201708109

M3 - 文章

C2 - 28901040

AN - SCOPUS:85030479396

SN - 1433-7851

VL - 56

SP - 13757

EP - 13761

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 44

ER -

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

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