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P.N. is grateful to the Irish Research Council for an Enterprise Partnership Postgraduate Scholarship (EPSPG/2021/173). J.G. acknowledges the Fundacion Ramon Areces for his postdoctoral fellowship (BEVP33P01S12222). We thank Science Foundation Ireland for supporting our research program through grants 20/FFP-P/8712, 19/IFA/7420, 18/ RI/5702 and 12/RC2275_P2. Duncan Guthrie (Vapourtec) is thanked for providing the reactor coils with embedded static mixer elements.

Analysis of institutional authors

García-Lacuna, JorgeAuthor

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September 26, 2024
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Continuous Flow Oxidation of Alcohols Using TEMPO/NaOCl for the Selective and Scalable Synthesis of Aldehydes

Publicated to:Organic Process Research & Development. 28 (5): 1587-1596 - 2024-05-01 28(5), DOI: 10.1021/acs.oprd.3c00237

Authors: Naik, Parth; Garcia-Lacuna, Jorge; O'Neill, Patrick; Baumann, Marcus

Affiliations

Pfizer Ireland, Ringaskiddy P43 X336, Ireland - Author
Univ Coll Dublin, Sch Chem, Sci Ctr South, Belfield D04 N2E5, Ireland - Author

Abstract

A simple and benign continuous flow oxidation protocol for the selective conversion of primary and secondary alcohols into their respective aldehyde and ketone products is reported. This approach makes use of catalytic amounts of TEMPO in combination with sodium bromide and sodium hypochlorite in a biphasic solvent system. A variety of substrates are tolerated including those containing heterocycles based on potentially sensitive nitrogen and sulfur moieties. The flow approach can be coupled with inline reactive extraction by formation of the carbonyl-bisulfite adduct which aids in separation of remaining substrate or other impurities. Process robustness is evaluated for the preparation of phenylpropanal at decagram scale, a trifluoromethylated oxazole building block as well as a late-stage intermediate for the anti-HIV drug maraviroc which demonstrates the potential value of this continuous oxidation method.

Keywords

AccessAciAerobic oxidationAldehydeBleachChemistryContinuous flowIn-line extractionKetonesScale-uTempoTempo-oxidation

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal Organic Process Research & Development due to its progression and the good impact it has achieved in recent years, according to the agency WoS (JCR), it has become a reference in its field. In the year of publication of the work, 2024 there are still no calculated indicators, but in 2023, it was in position 11/57, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Organic.

From a relative perspective, and based on the normalized impact indicator calculated from the Field Citation Ratio (FCR) of the Dimensions source, it yields a value of: 2.66, which indicates that, compared to works in the same discipline and in the same year of publication, it ranks as a work cited above average. (source consulted: Dimensions Aug 2025)

Specifically, and according to different indexing agencies, this work has accumulated citations as of 2025-08-02, the following number of citations:

  • WoS: 7
  • Europe PMC: 1

Impact and social visibility

From the perspective of influence or social adoption, and based on metrics associated with mentions and interactions provided by agencies specializing in calculating the so-called "Alternative or Social Metrics," we can highlight as of 2025-08-02:

  • The use, from an academic perspective evidenced by the Altmetric agency indicator referring to aggregations made by the personal bibliographic manager Mendeley, gives us a total of: 20.
  • The use of this contribution in bookmarks, code forks, additions to favorite lists for recurrent reading, as well as general views, indicates that someone is using the publication as a basis for their current work. This may be a notable indicator of future more formal and academic citations. This claim is supported by the result of the "Capture" indicator, which yields a total of: 20 (PlumX).

With a more dissemination-oriented intent and targeting more general audiences, we can observe other more global scores such as:

  • The Total Score from Altmetric: 5.8.
  • The number of mentions on the social network X (formerly Twitter): 9 (Altmetric).

Leadership analysis of institutional authors

This work has been carried out with international collaboration, specifically with researchers from: United Kingdom.