Peer Reviewed

1

Document Type

Article

Publication Date

20-6-2014

Keywords

Catalysis, Cations/*chemistry, Molecular Structure, Organometallic Compounds/*chemical synthesis/*chemistry, Organosilicon Compounds/*chemical synthesis/chemistry, Quaternary Ammonium Compounds/*chemical synthesis/*chemistry, Quinolizines/*chemistry, Sulfur Compounds/*chemistry, Trimethylsilyl Compounds/*chemical synthesis/*chemistry

Funder/Sponsor

European Research Association ERA-Chemistry and the Irish Research Council (IRC).

Comments

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher.

To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/jo5007637

Abstract

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.

Disciplines

Chemistry | Medicinal-Pharmaceutical Chemistry | Medicine and Health Sciences

Citation

Das M, O'Shea DF. Bu4N(+) Alkoxide-Initiated/Autocatalytic Addition Reactions with Organotrimethylsilanes. Journal of Organic chemistry. 2014;79(12):5595-607.

PubMed ID

24841115

DOI Link

10.1021/jo5007637

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