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Bu4N(+) Alkoxide-Initiated/Autocatalytic Addition Reactions with Organotrimethylsilanes.
Das, Manas; O'Shea, Donal F
<p>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.</p> <p>To access the final edited and published work see <a href="http://pubs.acs.org/doi/abs/10.1021/jo5007637">http://pubs.acs.org/doi/abs/10.1021/jo5007637</a></p> <p>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.</p>
Keyword(s): 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; Chemistry; Medicinal-Pharmaceutical Chemistry; Medicine and Health Sciences
Publication Date:
2014
Type: Journal article
Peer-Reviewed: Yes
Institution: Royal College of Surgeons in Ireland
Citation(s): Das M, O'Shea DF. Bu4N(+) Alkoxide-Initiated/Autocatalytic Addition Reactions with Organotrimethylsilanes. Journal of Organic chemistry. 2014;79(12):5595-607.
Publisher(s): American Chemical Society
File Format(s): application/pdf
Related Link(s): http://epubs.rcsi.ie/pmc/3/
First Indexed: 2015-07-31 15:36:38 Last Updated: 2018-02-13 07:20:12