Electrocatalytic dehydrogenative and defluorinative coupling between aldehyde-derived N,N-dialkylhydrazones and fluoromalonates: synthesis of 2-pyrazolines

Florent Noël; Laurent El Kaïm; Géraldine Masson; Aurélie Claraz

doi:10.1039/d4ob00588k

Electrocatalytic dehydrogenative and defluorinative coupling between aldehyde-derived N,N-dialkylhydrazones and fluoromalonates: synthesis of 2-pyrazolines

Florent Noël
, Laurent El Kaïm
, Géraldine Masson
, Aurélie Claraz

Research output: Contribution to journal › Article › peer-review

Abstract

An electrocatalytic synthesis of 2-pyrazolines via dehydrogenative and defluorinative cross-coupling reactions between (hetero)arylaldehyde-derived N,N-dialkylhydrazones and fluoromalonates is disclosed. Salient features of this work include (i) readily available starting materials, (ii) practical reaction conditions, and (ii) a formal oxidative (4 + 1)-cycloaddition via triple C-H bond functionalization. Cyclic voltammetry analyses support the electrocatalytic formation of an α-fluoromalonyl radical.

Original language	English
Pages (from-to)	4269-4273
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	22
Issue number	21
DOIs	https://doi.org/10.1039/d4ob00588k
Publication status	Published - 14 May 2024
Externally published	Yes

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title = "Electrocatalytic dehydrogenative and defluorinative coupling between aldehyde-derived N,N-dialkylhydrazones and fluoromalonates: synthesis of 2-pyrazolines",

abstract = "An electrocatalytic synthesis of 2-pyrazolines via dehydrogenative and defluorinative cross-coupling reactions between (hetero)arylaldehyde-derived N,N-dialkylhydrazones and fluoromalonates is disclosed. Salient features of this work include (i) readily available starting materials, (ii) practical reaction conditions, and (ii) a formal oxidative (4 + 1)-cycloaddition via triple C-H bond functionalization. Cyclic voltammetry analyses support the electrocatalytic formation of an α-fluoromalonyl radical.",

author = "Florent No{\"e}l and \{El Ka{\"i}m\}, Laurent and G{\'e}raldine Masson and Aur{\'e}lie Claraz",

note = "Publisher Copyright: {\textcopyright} 2024 The Royal Society of Chemistry",

year = "2024",

month = may,

day = "14",

doi = "10.1039/d4ob00588k",

language = "English",

volume = "22",

pages = "4269--4273",

journal = "Organic and Biomolecular Chemistry",

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Electrocatalytic dehydrogenative and defluorinative coupling between aldehyde-derived N,N-dialkylhydrazones and fluoromalonates: synthesis of 2-pyrazolines. / Noël, Florent; El Kaïm, Laurent; Masson, Géraldine et al.
In: Organic and Biomolecular Chemistry, Vol. 22, No. 21, 14.05.2024, p. 4269-4273.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Electrocatalytic dehydrogenative and defluorinative coupling between aldehyde-derived N,N-dialkylhydrazones and fluoromalonates

T2 - synthesis of 2-pyrazolines

AU - Noël, Florent

AU - El Kaïm, Laurent

AU - Masson, Géraldine

AU - Claraz, Aurélie

PY - 2024/5/14

Y1 - 2024/5/14

N2 - An electrocatalytic synthesis of 2-pyrazolines via dehydrogenative and defluorinative cross-coupling reactions between (hetero)arylaldehyde-derived N,N-dialkylhydrazones and fluoromalonates is disclosed. Salient features of this work include (i) readily available starting materials, (ii) practical reaction conditions, and (ii) a formal oxidative (4 + 1)-cycloaddition via triple C-H bond functionalization. Cyclic voltammetry analyses support the electrocatalytic formation of an α-fluoromalonyl radical.

AB - An electrocatalytic synthesis of 2-pyrazolines via dehydrogenative and defluorinative cross-coupling reactions between (hetero)arylaldehyde-derived N,N-dialkylhydrazones and fluoromalonates is disclosed. Salient features of this work include (i) readily available starting materials, (ii) practical reaction conditions, and (ii) a formal oxidative (4 + 1)-cycloaddition via triple C-H bond functionalization. Cyclic voltammetry analyses support the electrocatalytic formation of an α-fluoromalonyl radical.

U2 - 10.1039/d4ob00588k

DO - 10.1039/d4ob00588k

M3 - Article

C2 - 38742988

AN - SCOPUS:85193491280

SN - 1477-0520

VL - 22

SP - 4269

EP - 4273

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 21

ER -

Electrocatalytic dehydrogenative and defluorinative coupling between aldehyde-derived N,N-dialkylhydrazones and fluoromalonates: synthesis of 2-pyrazolines

Abstract

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