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Grant support

Financial support was provided by the Spanish Government (PID2021-122299NB-I00, TED2021-130470B-I00, TED2021-129999B-C32), 'Comunidad de Madrid', European Structural Funds (S2018/NMT-4367), proyectos sinergicos I + D (Y2020/NMT6469) and Comunidad Autonoma de Madrid (SI1/PJI/2019-00237). J. A. F.-S. thanks the Spanish Government for a Ramon y Cajal contract.

Analysis of institutional authors

Aleman, JoseCorresponding AuthorFernandez-Salas, Jose ACorresponding Author

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July 28, 2024
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Acyl radicals generated from aldehydes with NHPI as electrocatalyst: aldehydes and alcohols as carbon-centered radical precursors

Publicated to:Organic Chemistry Frontiers. 11 (17): 4842-4848 - 2024-07-17 11(17), DOI: 10.1039/d4qo01067a

Authors: Enríquez RG; Dato-Santiago JS; del Río-Rodríguez R; Alemán J; Fernández-Salas JA

Affiliations

Univ Autonoma Madrid, Ctr Innovat Adv Chem ORFEO CINQA, Madrid 28049, Spain - Author
Univ Autonoma Madrid, Inst Adv Res Chem Sci IAdChem, Madrid, Spain - Author
Univ Autonoma Madrid, Organ Chem Dept, Modulo 2, Madrid 28049, Spain - Author

Abstract

In this work, we describe how N-hydroxyphthalimide (NHPI) promotes hydrogen atom transfer from aldehydes under electrocatalytic chemical conditions. This involves the generation of phthalimide-N-oxyl (PINO), which abstracts an acyl hydrogen to produce acyl radicals from aldehydes. These acyl radicals then react with oximes or another PINO radical to form redox-active esters (RAEs). Additionally, we detail a Giese-type reaction with electron-deficient alkenes via electrochemical reduction of the generated RAE derivatives. This process produces sp3-carbon centered radicals from aldehydes. We also extend this method to aliphatic alcohols, involving a multi-step electrochemical process to form carbon-centered radicals from readily available alcohols. We describe how N-hydroxyphthalimide (NHPI) promotes hydrogen atom transfer from aldehydes under electrochemical conditions. NHPI plays a multifunctional role, enabling the consideration of aldehydes or alcohols as sp3-carbon centered radicals.

Keywords

BondEsterificationFunctionalizationGreen chemistryN-hydroxyphthalimide

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal Organic Chemistry Frontiers 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 6/58, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Organic. Notably, the journal is positioned above the 90th percentile.

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 2025-07-18:

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: 2.
  • The number of mentions on the social network X (formerly Twitter): 4 (Altmetric).

It is essential to present evidence supporting full alignment with institutional principles and guidelines on Open Science and the Conservation and Dissemination of Intellectual Heritage. A clear example of this is:

  • The work has been submitted to a journal whose editorial policy allows open Open Access publication.
  • Assignment of a Handle/URN as an identifier within the deposit in the Institutional Repository: https://repositorio.uam.es/handle/10486/714869

Leadership analysis of institutional authors

There is a significant leadership presence as some of the institution’s authors appear as the first or last signer, detailed as follows: First Author (Enriquez, Rodrigo G) and Last Author (FERNANDEZ SALAS, JOSE ANTONIO).

the authors responsible for correspondence tasks have been ALEMAN LARA, JOSE JULIAN and FERNANDEZ SALAS, JOSE ANTONIO.