Literature DB >> 29670964

Identifying the potential of pulsed LED irradiation in synthesis: copper-photocatalysed C-F functionalisation.

Thomas P Nicholls1, Johnathon C Robertson, Michael G Gardiner, Alex C Bissember.   

Abstract

It has been reported that pulsed irradiation can improve photosynthetic activity and phytochemical production in plants. Intrigued and inspired by these observations, we postulated that pulsed irradiation strategies may have broader implications in organic synthesis. We report here the results of a proof-of-concept study demonstrating that pulsed LED irradiation enhances the efficiency of a visible light-mediated photoredox-catalysed reaction. The design and construction of an inexpensive multiphase circuit (∼US$5) enabling power and pulse frequency modulation, which is connected to light-emitting diodes (LEDs), provides a source of pulsed visible light. This technology was then utilised to establish a novel copper-photocatalysed dual α-amino C-H/C-F functionalisation reaction. Pulsed blue LED irradiation was shown to be crucial for facilitating a much more efficient process and increasing the rate of product formation. Our results suggest that pulsed irradiation strategies have the potential to contribute to enhancing the synthetic utility and extending the scope of first row transition metal-based photoredox catalysts. We also anticipate that this approach will find wider applications in synthesis.

Entities:  

Year:  2018        PMID: 29670964     DOI: 10.1039/c8cc02244e

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  2 in total

1.  Prenyl Praxis: A Method for Direct Photocatalytic Defluoroprenylation.

Authors:  Sonal Priya; Jimmie D Weaver
Journal:  J Am Chem Soc       Date:  2018-11-15       Impact factor: 15.419

2.  Defluorodearomatization: A Photocatalytic Birch-Like Reduction That Enables C-C Bond Formation and Provides Access to Unnatural Cannabinoids.

Authors:  Jon I Day; Sascha Grotjahn; Sameera Senaweera; Burkhard Koenig; Jimmie D Weaver Iii
Journal:  J Org Chem       Date:  2021-06-02       Impact factor: 4.354

  2 in total

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