4.6 Article

A scalable continuous photochemical process for the generation of aminopropylsulfones

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 46, Pages -

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob01801e

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Funding

  1. School of Chemistry at UCD
  2. University College Dublin [SF1606, SF1609]
  3. Erasmus council
  4. Science Foundation Ireland [2018 18/RI/5702]
  5. Science Foundation Ireland (European Regional Development Fund) [12/RC2275_P2]

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An efficient continuous photochemical process is presented that delivers a series of novel gamma -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 gamma -aminopropylsulfone scaffolds in the future.

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