Jump to main content
US EPA
United States Environmental Protection Agency
Search
Search
Main menu
Environmental Topics
Laws & Regulations
About EPA
Health & Environmental Research Online (HERO)
Contact Us
Print
Feedback
Export to File
Search:
This record has one attached file:
Add More Files
Attach File(s):
Display Name for File*:
Save
Citation
Tags
HERO ID
7678536
Reference Type
Journal Article
Title
Direct coupling reaction between alcohols and silyl compounds: enhancement of Lewis acidity of Me3SiBr using InCl3
Author(s)
Saito, T; Nishimoto, Y; Yasuda, M; Baba, A
Year
2006
Is Peer Reviewed?
Yes
Journal
Journal of Organic Chemistry
ISSN:
0022-3263
EISSN:
1520-6904
Volume
71
Issue
22
Page Numbers
8516-8522
Language
English
PMID
17064028
DOI
10.1021/jo061512k
Web of Science Id
WOS:000241435600026
Abstract
The combination of InCl3 and Me3SiBr provided an enhanced Lewis acid system that can be used to promote a wide range of direct coupling reactions between alcohols and silyl nucleophiles in non-halogenated solvents, such as hexane or MeCN. The enhanced Lewis acidity of this system was measured by the 13C NMR in terms of the coordination to an alcohol. Moreover, the interaction between Me3SiBr and the In(III) species was revealed by 29Si NMR spectral analysis. Highly chemoselective allylations toward a hydroxyl moiety over ketone and acetoxy ones have been demonstrated.
Home
Learn about HERO
Using HERO
Search HERO
Projects in HERO
Risk Assessment
Transparency & Integrity