α-Functionalisation of Cyclic Sulfides Enabled by Lithiation Trapping

Abstract

A general and straightforward procedure for the lithiation / trapping of cyclic sulfides such as tetrahydrothiophene, tetrahydrothiopyran and a thiomorpholine is described. Trapping with a wide range of electrophiles is demonstrated, leading to more than 50 diverse α-substituted saturated sulfur heterocycles. The methodology provides access to a range of α-substituted cyclic sulfides that are not easily synthesised by the currently available methods.

Metadata

Item Type:

Article

Authors/Creators:

Seling, Nico (ns1091@york.ac.uk)
Atobe, Masakazu
Kasten, Kevin (kk941@york.ac.uk)
Firth, James D (jdf511@york.ac.uk)
Karadakov, Peter B https://orcid.org/0000-0002-2673-6804
Goldberg, Frederick W
O'Brien, Peter https://orcid.org/0000-0002-9966-1962

Copyright, Publisher and Additional Information:

© 2023 The Authors.

Keywords:

Organolithium, cyclic sulfides, α-functionalization

Dates:

Accepted: 17 November 2023
Published (online): 7 December 2023

Institution:

The University of York

Academic Units:

The University of York > Faculty of Sciences (York) > Chemistry (York)

Funding Information:

Funder	Grant number
THE ROYAL SOCIETY	INF\R1\191028
EPSRC	EP/P011217/1
EPSRC	EP/V048139/1

Depositing User:

Date Deposited:

27 Nov 2023 15:50

Last Modified:

11 Apr 2024 10:10

Published Version:

https://doi.org/10.1002/anie.202314423

Status:

Published online

Refereed:

Yes

Identification Number:

https://doi.org/10.1002/anie.202314423

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Filename: Angew_Chem_Int_Ed_-_2023_-_Seling_-_Functionalisation_of_Cyclic_Sulfides_Enabled_by_Lithiation_Trapping.pdf

Description: Functionalisation of Cyclic Sulfides Enabled by Lithiation Trapping

Licence: CC-BY 2.5

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