Bu4N(+) Alkoxide-Initiated/Autocatalytic Addition Reactions with Organotrimethylsilanes.

Das, Manas; O'Shea, Donal F.

Bu4N(+) Alkoxide-InitiatedAutocatalytic Addition Reactions with.pdf (1.08 MB)

Bu4N(+) Alkoxide-Initiated/Autocatalytic Addition Reactions with Organotrimethylsilanes.

Version 2 2022-03-10, 14:44

Version 1 2019-11-23, 11:50

journal contribution

posted on 2019-11-23, 11:50 authored by Manas Das, Donal F. O'Shea

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.

Funding

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

History

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

Published Citation

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