Mechanochemical metal-free transfer Hydrogenation of carbonyls using polymethylhydrosiloxane as the hydrogen source
File(s)
Author(s)
Li, Alain Y
Segalla, Andreanne
Li, Chao-Jun
Moores, Audrey
Type
Journal Article
Abstract
We report herein a new methodology for the rapid and selective reduction of carbonyls in the solid phase. By exploiting mechanical energy and using a cheap and air-stable silane, polymethylhydrosiloxane (PMHS), we can reduce a variety of carbonyl compounds, with catalytic amounts of fluorides. A scope of 19 substrates was explored to probe the generality of the method. In addition, an important biomass-based platform chemical, 5-hydroxymethylfurfural (5-HMF), and an insoluble polymer, polyketone, could be reduced with this methodology. A mechanistic study is also presented, suggesting the active role of volatile silane species. This method is particularly appealing to overcome substrate solubility issues and reduce solvent reliance in organic synthesis.
Date Issued
2017-12-04
Date Acceptance
2017-11-01
Citation
ACS Sustainable Chemistry and Engineering, 2017, 5 (12), pp.11752-11760
ISSN
2168-0485
Publisher
American Chemical Society
Start Page
11752
End Page
11760
Journal / Book Title
ACS Sustainable Chemistry and Engineering
Volume
5
Issue
12
Copyright Statement
© 2017 American Chemical Society.
Identifier
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000417341900069&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=1ba7043ffcc86c417c072aa74d649202
Subjects
Science & Technology
Physical Sciences
Technology
Chemistry, Multidisciplinary
Green & Sustainable Science & Technology
Engineering, Chemical
Chemistry
Science & Technology - Other Topics
Engineering
Mechanochemistry
Carbonyl reduction
PMHS
HMF
Polyketone
Transfer hydrogenation
REDUCTION
KETONES
ESTERS
HYDROSILYLATION
ALDEHYDES
COPOLYMERIZATION
CATALYSTS
BIOMASS
CO2
Publication Status
Published
Date Publish Online
2017-11-16