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Analysis of institutional authors

Gadekar, ScAuthor

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January 9, 2023
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Rerouting the Organocatalytic Benzoin Reaction toward Aldehyde Deuteration

Publicated to: Acs Catalysis. 11 (23): 14561-14569 - 2021-12-03 11(23), DOI: 10.1021/acscatal.1c04583

Authors:

Gadekar, Santosh C; Dhayalan, Vasudevan; Nandi, Ashim; Zak, Inbal L; Mizrachi, Meital Shema; Kozuch, Sebastian; Milo, Anat
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Affiliations

Ben Gurion Univ Negev, Dept Chem, IL-84105 Beer Sheva, Israel - Author
Inst Chem Res Catalonia ICIQ, Tarragona, Spain - Author
Natl Inst Technol Puducherry NITPY, Dept Chem, Pondicherry, India - Author
Weizmann Inst Sci, Dept Mol Chem & Mat Sci, IL-7610001 Rehovot, Israel - Author
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Abstract

Reactive intermediates are key to halting and promoting chemical transformations; however, due to their elusive nature, they are not straightforwardly harnessed for reaction design. Herein, we describe studies aimed at stabilizing reactive intermediates in the N-heterocyclic carbene (NHC) catalytic cycle, which enabled the full shutdown of the known benzoin coupling pathway, while rerouting its intermediates toward deuteration. The reversible nature of NHC catalysis and the selective stabilization of reaction intermediates facilitated clean hydrogen-deuterium exchange reactions of aromatic aldehydes by D2O, even for challenging electron-withdrawing substrates. In several cases, the addition of catalytic amounts of phenyl boronic acid was used to further stabilize highly reactive intermediates and mitigate the formation of benzoin coupling byproducts. The mechanistic understanding at the foundation of this work resulted in unprecedented mild conditions with base and catalyst loadings as low as 0.1 mol %, and a scalable deuteration reaction applicable to a broad substrate scope with outstanding functional group tolerance. More importantly, adopting this approach enabled the construction of a guideline for identifying the appropriate catalyst and conditions for different substrates. Experimental studies combined with machine learning and computational methods shed light on the nontrivial mechanistic underpinnings of this reaction.
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Keywords

Boronic acidChemistryData scienceDeuterationDeuteriumH/d exchangeMechanismN-heterocyclic carbeneN-heterocyclic carbenesOrganocatalysisSecondary sphereThiamine action

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal Acs Catalysis 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, 2021, it was in position 19/165, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Physical.

Independientemente del impacto esperado determinado por el canal de difusión, es importante destacar el impacto real observado de la propia aportación.

Según las diferentes agencias de indexación, el número de citas acumuladas por esta publicación hasta la fecha 2026-01-01:

  • WoS: 22
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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 2026-01-01:

  • 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: 32.
  • 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: 32 (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: 7.
  • The number of mentions on the social network Facebook: 1 (Altmetric).
  • The number of mentions on the social network X (formerly Twitter): 11 (Altmetric).
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Leadership analysis of institutional authors

This work has been carried out with international collaboration, specifically with researchers from: India; Israel.

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 (Gadekar, Santosh C.) .

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Awards linked to the item

This research was supported by the Israel Science Foundation (Grants No. 1193/17 and 2252/21). The authors thank Doron Pappo for fruitful discussions. V.D. gratefully acknowledges the PBC for a postdoctoral fellowship. S.C.G. gratefully acknowledges the Kreitman Graduate School for a postdoctoral fellowship.
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