Bu4N+ Alkoxide-Initiated/Autocatalytic Addition Reactions with Organotrimethylsilanes

The use of Me3SiO–/Bu4N+ as a general activator of organotrimethylsilanes for addition reactions has been established. The broad scope of the method offers trimethylsilanes (including acetate, allyl, propargyl, benzyl, dithiane, heteroaryl, and aryl derivatives) as bench-stable organometallics that...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2014-06, Vol.79 (12), p.5595-5607
Main Authors: Das, Manas, O’Shea, Donal F
Format: Article
Language:English
Subjects:
Catalysis
Cations - chemistry
Molecular Structure
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Organosilicon Compounds - chemical synthesis
Organosilicon Compounds - chemistry
Quaternary Ammonium Compounds - chemical synthesis
Quaternary Ammonium Compounds - chemistry
Quinolizines - chemistry
Sulfur Compounds - chemistry
Trimethylsilyl Compounds - chemical synthesis
Trimethylsilyl Compounds - chemistry
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The use of Me3SiO–/Bu4N+ as a general activator of organotrimethylsilanes for addition reactions has been established. The broad scope of the method offers trimethylsilanes (including acetate, allyl, propargyl, benzyl, dithiane, heteroaryl, and aryl derivatives) as bench-stable organometallics that can be readily utilized as carbanion equivalents for synthesis. Reactions are achieved at rt without the requirement of specialized precautions that are commonplace for other organometallics.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5007637