On the N-Arylation of Acetamide Using 2-, 3- and 1’-Substituted Iodoferrocenes**

Lingaswamy Kadari; William Erb; Yury S. Halauko; Oleg A. Ivashkevich; Vadim E. Matulis; Dmitry Lyakhov; Thierry Roisnel; Palakodety Radha Krishna; Florence Mongin

doi:10.1002/ejic.202000904

On the N-Arylation of Acetamide Using 2-, 3- and 1’-Substituted Iodoferrocenes**

Lingaswamy Kadari, William Erb, Yury S. Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, Dmitry Lyakhov, Thierry Roisnel, Palakodety Radha Krishna, Florence Mongin

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Abstract

Various 2-, 3- and 1’-substituted iodoferrocenes were reacted with acetamide in the presence of copper(I) iodide (1 equiv), N,N’-dimethylethylenediamine (1 equiv), tripotassium phosphate (2 equiv) in dioxane at 90 °C for 14 h, and allowed a large range of original 1,2-, 1,3- and 1,1’-disubstituted ferrocenes to be obtained. The results were compared as a function of the substituent and its position on the ring. DFT calculations revealed higher activation barrier for the oxidative addition in the ferrocene series when compared with classical planar aromatics. Structure-property relationships were applied to rationalize the reactivity of the different iodoferrocenes.

Original language	English (US)
Journal	European Journal of Inorganic Chemistry
DOIs	https://doi.org/10.1002/ejic.202000904
State	Published - Dec 22 2020

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KAUST Repository Item: Exported on 2020-12-28

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10.1002/ejic.202000904

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title = "On the N-Arylation of Acetamide Using 2-, 3- and 1{\textquoteright}-Substituted Iodoferrocenes**",

abstract = "Various 2-, 3- and 1{\textquoteright}-substituted iodoferrocenes were reacted with acetamide in the presence of copper(I) iodide (1 equiv), N,N{\textquoteright}-dimethylethylenediamine (1 equiv), tripotassium phosphate (2 equiv) in dioxane at 90 °C for 14 h, and allowed a large range of original 1,2-, 1,3- and 1,1{\textquoteright}-disubstituted ferrocenes to be obtained. The results were compared as a function of the substituent and its position on the ring. DFT calculations revealed higher activation barrier for the oxidative addition in the ferrocene series when compared with classical planar aromatics. Structure-property relationships were applied to rationalize the reactivity of the different iodoferrocenes.",

author = "Lingaswamy Kadari and William Erb and Halauko, {Yury S.} and Ivashkevich, {Oleg A.} and Matulis, {Vadim E.} and Dmitry Lyakhov and Thierry Roisnel and {Radha Krishna}, Palakodety and Florence Mongin",

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year = "2020",

month = dec,

day = "22",

doi = "10.1002/ejic.202000904",

language = "English (US)",

journal = "European Journal of Inorganic Chemistry",

issn = "1099-0682",

publisher = "Wiley-VCH Verlag",

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T1 - On the N-Arylation of Acetamide Using 2-, 3- and 1’-Substituted Iodoferrocenes**

AU - Kadari, Lingaswamy

AU - Erb, William

AU - Halauko, Yury S.

AU - Ivashkevich, Oleg A.

AU - Matulis, Vadim E.

AU - Lyakhov, Dmitry

AU - Roisnel, Thierry

AU - Radha Krishna, Palakodety

AU - Mongin, Florence

N1 - KAUST Repository Item: Exported on 2020-12-28

PY - 2020/12/22

Y1 - 2020/12/22

N2 - Various 2-, 3- and 1’-substituted iodoferrocenes were reacted with acetamide in the presence of copper(I) iodide (1 equiv), N,N’-dimethylethylenediamine (1 equiv), tripotassium phosphate (2 equiv) in dioxane at 90 °C for 14 h, and allowed a large range of original 1,2-, 1,3- and 1,1’-disubstituted ferrocenes to be obtained. The results were compared as a function of the substituent and its position on the ring. DFT calculations revealed higher activation barrier for the oxidative addition in the ferrocene series when compared with classical planar aromatics. Structure-property relationships were applied to rationalize the reactivity of the different iodoferrocenes.

AB - Various 2-, 3- and 1’-substituted iodoferrocenes were reacted with acetamide in the presence of copper(I) iodide (1 equiv), N,N’-dimethylethylenediamine (1 equiv), tripotassium phosphate (2 equiv) in dioxane at 90 °C for 14 h, and allowed a large range of original 1,2-, 1,3- and 1,1’-disubstituted ferrocenes to be obtained. The results were compared as a function of the substituent and its position on the ring. DFT calculations revealed higher activation barrier for the oxidative addition in the ferrocene series when compared with classical planar aromatics. Structure-property relationships were applied to rationalize the reactivity of the different iodoferrocenes.

UR - http://hdl.handle.net/10754/666657

UR - https://onlinelibrary.wiley.com/doi/10.1002/ejic.202000904

UR - http://www.scopus.com/inward/record.url?scp=85097885674&partnerID=8YFLogxK

U2 - 10.1002/ejic.202000904

DO - 10.1002/ejic.202000904

M3 - Article

SN - 1099-0682

JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

ER -

On the N-Arylation of Acetamide Using 2-, 3- and 1’-Substituted Iodoferrocenes**

Abstract

Bibliographical note

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CCDC 2026534: Experimental Crystal Structure Determination : N-(1'-methylferrocenyl)acetamide

CCDC 2026537: Experimental Crystal Structure Determination : N-(3-(methoxycarbonyl)ferrocenyl)acetamide hemihydrate

CCDC 2026535: Experimental Crystal Structure Determination : N-(1'-formylferrocenyl)acetamide

Cite this

On the N-Arylation of Acetamide Using 2-, 3- and 1’-Substituted Iodoferrocenes**

Abstract

Bibliographical note

Access to Document

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Datasets

CCDC 2026534: Experimental Crystal Structure Determination : N-(1'-methylferrocenyl)acetamide

CCDC 2026537: Experimental Crystal Structure Determination : N-(3-(methoxycarbonyl)ferrocenyl)acetamide hemihydrate

CCDC 2026535: Experimental Crystal Structure Determination : N-(1'-formylferrocenyl)acetamide

Cite this