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A scalable continuous photochemical process for the generation of aminopropylsulfones.
Bonciolini, Stefano; Di Filippo, Mara; Baumann, Marcus.
Afiliación
  • Bonciolini S; School of Chemistry, University College Dublin, Science Centre South, Belfield, D04 N2E2, Ireland. marcus.baumann@ucd.ie.
  • Di Filippo M; School of Chemistry, University College Dublin, Science Centre South, Belfield, D04 N2E2, Ireland. marcus.baumann@ucd.ie.
  • Baumann M; School of Chemistry, University College Dublin, Science Centre South, Belfield, D04 N2E2, Ireland. marcus.baumann@ucd.ie.
Org Biomol Chem ; 18(46): 9428-9432, 2020 12 07.
Article en En | MEDLINE | ID: mdl-32969443
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.

Texto completo: 1 Banco de datos: MEDLINE Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2020 Tipo del documento: Article País de afiliación: Irlanda

Texto completo: 1 Banco de datos: MEDLINE Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2020 Tipo del documento: Article País de afiliación: Irlanda