Activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(sp(3))–H amidation, C(sp(2))–H iodination, and perfluoroalkylation reactions

A simple, efficient, and convenient activation of perfluoroalkyl iodides by tBuONa or KOH, without expensive photo- or transition metal catalysts, allows the promotion of versatile α-sp(3) C–H amidation reactions of alkyl ethers and benzylic hydrocarbons, C–H iodination of heteroaryl compounds, and...

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Autores principales: Wang, Yaxin, Cao, Zehui, He, Qin, Huang, Xin, Liu, Jiaxi, Neumann, Helfried, Chen, Gong, Beller, Matthias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9930934/
https://www.ncbi.nlm.nih.gov/pubmed/36819859
http://dx.doi.org/10.1039/d2sc06145g
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author Wang, Yaxin
Cao, Zehui
He, Qin
Huang, Xin
Liu, Jiaxi
Neumann, Helfried
Chen, Gong
Beller, Matthias
author_facet Wang, Yaxin
Cao, Zehui
He, Qin
Huang, Xin
Liu, Jiaxi
Neumann, Helfried
Chen, Gong
Beller, Matthias
author_sort Wang, Yaxin
collection PubMed
description A simple, efficient, and convenient activation of perfluoroalkyl iodides by tBuONa or KOH, without expensive photo- or transition metal catalysts, allows the promotion of versatile α-sp(3) C–H amidation reactions of alkyl ethers and benzylic hydrocarbons, C–H iodination of heteroaryl compounds, and perfluoroalkylations of electron-rich π bonds. Mechanistic studies show that these novel protocols are based on the halogen bond interaction between perfluoroalkyl iodides and tBuONa or KOH, which promote homolysis of perfluoroalkyl iodides under mild conditions.
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spelling pubmed-99309342023-02-16 Activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(sp(3))–H amidation, C(sp(2))–H iodination, and perfluoroalkylation reactions Wang, Yaxin Cao, Zehui He, Qin Huang, Xin Liu, Jiaxi Neumann, Helfried Chen, Gong Beller, Matthias Chem Sci Chemistry A simple, efficient, and convenient activation of perfluoroalkyl iodides by tBuONa or KOH, without expensive photo- or transition metal catalysts, allows the promotion of versatile α-sp(3) C–H amidation reactions of alkyl ethers and benzylic hydrocarbons, C–H iodination of heteroaryl compounds, and perfluoroalkylations of electron-rich π bonds. Mechanistic studies show that these novel protocols are based on the halogen bond interaction between perfluoroalkyl iodides and tBuONa or KOH, which promote homolysis of perfluoroalkyl iodides under mild conditions. The Royal Society of Chemistry 2023-01-24 /pmc/articles/PMC9930934/ /pubmed/36819859 http://dx.doi.org/10.1039/d2sc06145g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Wang, Yaxin
Cao, Zehui
He, Qin
Huang, Xin
Liu, Jiaxi
Neumann, Helfried
Chen, Gong
Beller, Matthias
Activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(sp(3))–H amidation, C(sp(2))–H iodination, and perfluoroalkylation reactions
title Activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(sp(3))–H amidation, C(sp(2))–H iodination, and perfluoroalkylation reactions
title_full Activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(sp(3))–H amidation, C(sp(2))–H iodination, and perfluoroalkylation reactions
title_fullStr Activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(sp(3))–H amidation, C(sp(2))–H iodination, and perfluoroalkylation reactions
title_full_unstemmed Activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(sp(3))–H amidation, C(sp(2))–H iodination, and perfluoroalkylation reactions
title_short Activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(sp(3))–H amidation, C(sp(2))–H iodination, and perfluoroalkylation reactions
title_sort activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to c(sp(3))–h amidation, c(sp(2))–h iodination, and perfluoroalkylation reactions
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9930934/
https://www.ncbi.nlm.nih.gov/pubmed/36819859
http://dx.doi.org/10.1039/d2sc06145g
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