A scalable continuous photochemical process for the generation of aminopropylsulfones.


Journal

Organic & biomolecular chemistry
ISSN: 1477-0539
Titre abrégé: Org Biomol Chem
Pays: England
ID NLM: 101154995

Informations de publication

Date de publication:
07 12 2020
Historique:
pubmed: 25 9 2020
medline: 25 9 2020
entrez: 24 9 2020
Statut: ppublish

Résumé

An efficient continuous photochemical process is presented that delivers a series of novel γ-aminopropylsulfones via a tetrabutylammonium decatungstate (TBADT) catalysed HAT-process. Crucial to this success is the exploitation of a new high-power LED emitting at 365 nm that was found to be superior to an alternative medium-pressure Hg lamp. The resulting flow process enabled the scale-up of this transformation reaching throughputs of 20 mmol h-1 at substrate concentrations up to 500 mM. Additionally, the substrate scope of this transformation was evaluated demonstrating the straightforward incorporation of different amine substituents as well as alkyl appendages next to the sulfone moiety. It is anticipated that this methodology will allow for further exploitations of these underrepresented γ-aminopropylsulfone scaffolds in the future.

Identifiants

pubmed: 32969443
doi: 10.1039/d0ob01801e
doi:

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

9428-9432

Auteurs

Stefano Bonciolini (S)

School of Chemistry, University College Dublin, Science Centre South, Belfield, D04 N2E2, Ireland. marcus.baumann@ucd.ie.

Mara Di Filippo (M)

School of Chemistry, University College Dublin, Science Centre South, Belfield, D04 N2E2, Ireland. marcus.baumann@ucd.ie.

Marcus Baumann (M)

School of Chemistry, University College Dublin, Science Centre South, Belfield, D04 N2E2, Ireland. marcus.baumann@ucd.ie.

Classifications MeSH