journal article

Journal Article

Text

Journal of the American Chemical Society. 2022, 144(15), p. 6714-6718

Non-Stabilized Vinyl Anion Equivalents from Styrenes by N-Heterocyclic Carbene Catalysis and Its Use in Catalytic Nucleophilic Aromatic Substitution

American Chemical Society

English

Text

2022-04-11

https://doi.org/10.1021/jacs.2c02579

Ito S., Fujimoto H., Tobisu M.. Non-Stabilized Vinyl Anion Equivalents from Styrenes by N-Heterocyclic Carbene Catalysis and Its Use in Catalytic Nucleophilic Aromatic Substitution. Journal of the American Chemical Society, 144, 15, 6714-6718, April 11, 2022. © 2022 American Chemical Society. https://doi.org/10.1021/jacs.2c02579.

A protocol for the catalytic nucleophilic activation of unactivated styrenes is reported, which enables the generation of a non-stabilized alkenyl anion equivalent as a transient intermediate. In the reaction, N-heterocyclic carbenes add across styrenes to generate ylide intermediates, which can then be used in intramolecular nucleophilic aromatic substitution reactions of aryl fluorides, chlorides, and methyl ethers. The method allows for straightforward access to complex polyaromatic compounds.

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jacs.2c02579.

88317

Non-Stabilized Vinyl Anion Equivalents from Styrenes by N-Heterocyclic Carbene Catalysis and Its Use in Catalytic Nucleophilic Aromatic Substitution

American Chemical Society

English

2022-04-11

Journal of the American Chemical Society

144

15

6714

6718

https://doi.org/10.1021/jacs.2c02579

35404600

https://hdl.handle.net/11094/88317