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A scalable continuous photochemical process for the generation of aminopropylsulfones

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Abstract

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.

Graphical abstract: A scalable continuous photochemical process for the generation of aminopropylsulfones

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Article information


Submitted
31 Aug 2020
Accepted
18 Sep 2020
First published
18 Sep 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

A scalable continuous photochemical process for the generation of aminopropylsulfones

S. Bonciolini, M. Di Filippo and M. Baumann, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB01801E

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