Ether Synthesis through Reductive Cross-Coupling of Ketones with Alcohols Using Me 2 SiHCl as both Reductant and Lewis Acid

Yong Ho Lee; Bill Morandi

doi:10.1055/s-0036-1590838

Ether Synthesis through Reductive Cross-Coupling of Ketones with Alcohols Using Me ₂ SiHCl as both Reductant and Lewis Acid

Yong Ho Lee, Bill Morandi

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

We report that a Lewis acidic silane, Me ₂ SiHCl, can mediate the direct cross-coupling of a wide range of carbonyl compounds with alcohols to form dialkyl ethers. The reaction is operationally simple, tolerates a range of polar functional groups, can be utilized to make sterically hindered ethers, and is extendable to sulfur and nitrogen nucleophiles.

Original language	English
Pages (from-to)	2425-2428
Number of pages	4
Journal	Synlett
Volume	28
Issue number	18
DOIs	https://doi.org/10.1055/s-0036-1590838
Publication status	Published - 2017 Nov 13
Externally published	Yes

Keywords

alcohols
ethers
ketones
Lewis acid
reductive coupling
silanes

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-0036-1590838

Cite this

@article{5e0bb2acea814caea11cec370f5434dd,

title = "Ether Synthesis through Reductive Cross-Coupling of Ketones with Alcohols Using Me 2 SiHCl as both Reductant and Lewis Acid",

abstract = "We report that a Lewis acidic silane, Me 2 SiHCl, can mediate the direct cross-coupling of a wide range of carbonyl compounds with alcohols to form dialkyl ethers. The reaction is operationally simple, tolerates a range of polar functional groups, can be utilized to make sterically hindered ethers, and is extendable to sulfur and nitrogen nucleophiles.",

keywords = "alcohols, ethers, ketones, Lewis acid, reductive coupling, silanes",

author = "Lee, {Yong Ho} and Bill Morandi",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart.New York.",

year = "2017",

month = nov,

day = "13",

doi = "10.1055/s-0036-1590838",

language = "English",

volume = "28",

pages = "2425--2428",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "18",

}

TY - JOUR

T1 - Ether Synthesis through Reductive Cross-Coupling of Ketones with Alcohols Using Me 2 SiHCl as both Reductant and Lewis Acid

AU - Lee, Yong Ho

AU - Morandi, Bill

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart.New York.

PY - 2017/11/13

Y1 - 2017/11/13

N2 - We report that a Lewis acidic silane, Me 2 SiHCl, can mediate the direct cross-coupling of a wide range of carbonyl compounds with alcohols to form dialkyl ethers. The reaction is operationally simple, tolerates a range of polar functional groups, can be utilized to make sterically hindered ethers, and is extendable to sulfur and nitrogen nucleophiles.

AB - We report that a Lewis acidic silane, Me 2 SiHCl, can mediate the direct cross-coupling of a wide range of carbonyl compounds with alcohols to form dialkyl ethers. The reaction is operationally simple, tolerates a range of polar functional groups, can be utilized to make sterically hindered ethers, and is extendable to sulfur and nitrogen nucleophiles.

KW - alcohols

KW - ethers

KW - ketones

KW - Lewis acid

KW - reductive coupling

KW - silanes

UR - http://www.scopus.com/inward/record.url?scp=85025612379&partnerID=8YFLogxK

U2 - 10.1055/s-0036-1590838

DO - 10.1055/s-0036-1590838

M3 - Article

AN - SCOPUS:85025612379

VL - 28

SP - 2425

EP - 2428

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 18

ER -