How electrophilic are 3-nitroindoles? Mechanistic investigations and application to a reagentless (4+2) cycloaddition

Batoul Rkein; Maxime Manneveau; Ludovik Noël-Duchesneau; Karine Pasturaud; Muriel Durandetti; Julien Legros; Sami Lakhdar; Isabelle Chataigner

doi:10.1039/d1cc04074j

How electrophilic are 3-nitroindoles? Mechanistic investigations and application to a reagentless (4+2) cycloaddition

Batoul Rkein
, Maxime Manneveau
, Ludovik Noël-Duchesneau
, Karine Pasturaud
, Muriel Durandetti
, Julien Legros
, Sami Lakhdar
, Isabelle Chataigner

Normandie Université
Normandie Université
Université Paul Sabatier
Sorbonne Université

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

20 Citations (Scopus)

Abstract

The electrophilicity of 4 different 3-nitroindole derivatives has been evaluated by Mayr’s linear free energy relationship (log k(20 °C) =s_N(E+N)) and reveals unexpected values for aromatic compounds, in the nitrostyrene range. 3-Nitroindoles are sufficiently electrophilic to interact with a common diene namely the Danishefsky's diene at room temperature, in the absence of any activator, to furnish smoothly the dearomatized (4+2) cycloadducts in good yields.

Original language	English
Pages (from-to)	10071-10074
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	78
DOIs	https://doi.org/10.1039/d1cc04074j
Publication status	Published - 7 Oct 2021
Externally published	Yes

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10.1039/d1cc04074j

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abstract = "The electrophilicity of 4 different 3-nitroindole derivatives has been evaluated by Mayr{\textquoteright}s linear free energy relationship (log k(20 °C) =sN(E+N)) and reveals unexpected values for aromatic compounds, in the nitrostyrene range. 3-Nitroindoles are sufficiently electrophilic to interact with a common diene namely the Danishefsky's diene at room temperature, in the absence of any activator, to furnish smoothly the dearomatized (4+2) cycloadducts in good yields.",

author = "Batoul Rkein and Maxime Manneveau and Ludovik No{\"e}l-Duchesneau and Karine Pasturaud and Muriel Durandetti and Julien Legros and Sami Lakhdar and Isabelle Chataigner",

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AU - Rkein, Batoul

AU - Manneveau, Maxime

AU - Noël-Duchesneau, Ludovik

AU - Pasturaud, Karine

AU - Durandetti, Muriel

AU - Legros, Julien

AU - Lakhdar, Sami

AU - Chataigner, Isabelle

PY - 2021/10/7

Y1 - 2021/10/7

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AB - The electrophilicity of 4 different 3-nitroindole derivatives has been evaluated by Mayr’s linear free energy relationship (log k(20 °C) =sN(E+N)) and reveals unexpected values for aromatic compounds, in the nitrostyrene range. 3-Nitroindoles are sufficiently electrophilic to interact with a common diene namely the Danishefsky's diene at room temperature, in the absence of any activator, to furnish smoothly the dearomatized (4+2) cycloadducts in good yields.

UR - https://www.scopus.com/pages/publications/85116032317

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DO - 10.1039/d1cc04074j

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VL - 57

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EP - 10074

JO - Chemical Communications

JF - Chemical Communications

IS - 78

ER -

How electrophilic are 3-nitroindoles? Mechanistic investigations and application to a reagentless (4+2) cycloaddition

Abstract

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