Catalytic Reduction of Cyclic Ethers with Hydrosilanes

Sehoon Park

doi:10.1002/asia.201900330

Catalytic Reduction of Cyclic Ethers with Hydrosilanes

Sehoon Park^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Review article › peer-review

15 Scopus citations

Abstract

Catalytic reductive transformations of ethers as a synthetic building block are an important class of chemical reactions because a range of essential chemical feedstocks and fuels in contemporary life can be prepared through the key step of ethereal C−O bond cleavage of cellulosic biomass. Although conventional stoichiometric and catalytic methods for sp²- and sp³-C−O bond cleavage of linear ethers and alcohols with hydrosilanes are well established, silylative ring opening of cyclic ethers has been less highlighted in this context. This review outlines catalytic systems for the silylative reduction of a range of cyclic ethers, including epoxides and sugars, leading to the corresponding alcohols and/or hydrocarbons. The chemical reactivity and selectivity of these ring-opening catalytic processes are discussed with respect to the type of substrates; the representative catalytic working modes are also described.

Original language	English
Pages (from-to)	2048-2066
Number of pages	19
Journal	Chemistry - An Asian Journal
Volume	14
Issue number	12
DOIs	https://doi.org/10.1002/asia.201900330
State	Published - 14 Jun 2019

Keywords

C−O bond cleavage
biomass
cyclic ethers
homogeneous catalysis
reduction

Access to Document

10.1002/asia.201900330

Cite this

@article{017b190286a74b77950178e68643a7a4,

title = "Catalytic Reduction of Cyclic Ethers with Hydrosilanes",

abstract = "Catalytic reductive transformations of ethers as a synthetic building block are an important class of chemical reactions because a range of essential chemical feedstocks and fuels in contemporary life can be prepared through the key step of ethereal C−O bond cleavage of cellulosic biomass. Although conventional stoichiometric and catalytic methods for sp2- and sp3-C−O bond cleavage of linear ethers and alcohols with hydrosilanes are well established, silylative ring opening of cyclic ethers has been less highlighted in this context. This review outlines catalytic systems for the silylative reduction of a range of cyclic ethers, including epoxides and sugars, leading to the corresponding alcohols and/or hydrocarbons. The chemical reactivity and selectivity of these ring-opening catalytic processes are discussed with respect to the type of substrates; the representative catalytic working modes are also described.",

keywords = "C−O bond cleavage, biomass, cyclic ethers, homogeneous catalysis, reduction",

author = "Sehoon Park",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

month = jun,

day = "14",

doi = "10.1002/asia.201900330",

language = "英语",

volume = "14",

pages = "2048--2066",

journal = "Chemistry - An Asian Journal",

issn = "1861-4728",

publisher = "John Wiley and Sons Ltd",

number = "12",

}

TY - JOUR

T1 - Catalytic Reduction of Cyclic Ethers with Hydrosilanes

AU - Park, Sehoon

PY - 2019/6/14

Y1 - 2019/6/14

N2 - Catalytic reductive transformations of ethers as a synthetic building block are an important class of chemical reactions because a range of essential chemical feedstocks and fuels in contemporary life can be prepared through the key step of ethereal C−O bond cleavage of cellulosic biomass. Although conventional stoichiometric and catalytic methods for sp2- and sp3-C−O bond cleavage of linear ethers and alcohols with hydrosilanes are well established, silylative ring opening of cyclic ethers has been less highlighted in this context. This review outlines catalytic systems for the silylative reduction of a range of cyclic ethers, including epoxides and sugars, leading to the corresponding alcohols and/or hydrocarbons. The chemical reactivity and selectivity of these ring-opening catalytic processes are discussed with respect to the type of substrates; the representative catalytic working modes are also described.

AB - Catalytic reductive transformations of ethers as a synthetic building block are an important class of chemical reactions because a range of essential chemical feedstocks and fuels in contemporary life can be prepared through the key step of ethereal C−O bond cleavage of cellulosic biomass. Although conventional stoichiometric and catalytic methods for sp2- and sp3-C−O bond cleavage of linear ethers and alcohols with hydrosilanes are well established, silylative ring opening of cyclic ethers has been less highlighted in this context. This review outlines catalytic systems for the silylative reduction of a range of cyclic ethers, including epoxides and sugars, leading to the corresponding alcohols and/or hydrocarbons. The chemical reactivity and selectivity of these ring-opening catalytic processes are discussed with respect to the type of substrates; the representative catalytic working modes are also described.

KW - C−O bond cleavage

KW - biomass

KW - cyclic ethers

KW - homogeneous catalysis

KW - reduction

UR - http://www.scopus.com/inward/record.url?scp=85066272899&partnerID=8YFLogxK

U2 - 10.1002/asia.201900330

DO - 10.1002/asia.201900330

M3 - 文献综述

C2 - 30938932

AN - SCOPUS:85066272899

SN - 1861-4728

VL - 14

SP - 2048

EP - 2066

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

IS - 12

ER -

Catalytic Reduction of Cyclic Ethers with Hydrosilanes

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this