A Class of Effective of Decarboxylative Perfluoroalkylating Reagents: [(phen)2Cu](O2CRF)

Yangjie Huang; Manjaly John Ajitha; Kuo-Wei Huang; Zhongxing Zhang; Zhiqiang Weng

doi:10.1039/C6DT00277C

A Class of Effective of Decarboxylative Perfluoroalkylating Reagents: [(phen)2Cu](O2CRF)

Yangjie Huang, Manjaly John Ajitha, Kuo-Wei Huang, Zhongxing Zhang, Zhiqiang Weng

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

25 Scopus citations

Abstract

This article describes the invention of a class of effective reagents [(phen)2Cu](O2CRF) (1) for the decarboxylative perfluoroalkylation of aryl and heteroaryl halides. Treatment of the copper tert-butyloxide with phenanthroline ligands, with subsequent addition of perfluorocarboxylic acids afforded the air-stable copper(I) perfluorocarboxylato complexes 1. These complexes reacted with a variety of aryl and heteroaryl halides to form perfluoroalkyl(hetero)arenes in moderate to high yields. Computational studies suggested that the coordination of the second phen ligand may reduce the energy barrier for the decarboxylation of perfluorocarboxylate to facilitate the perfluoroalkylation.

Original language	English (US)
Pages (from-to)	8468-8474
Number of pages	7
Journal	Dalton Trans.
Volume	45
Issue number	20
DOIs	https://doi.org/10.1039/C6DT00277C
State	Published - 2016

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: Financial support from the National Natural Science
Foundation of China (NSFC) (grant number 21372044), the
Research Fund for the Doctoral Program of Higher Education
of China (grant number 20123514110003), and Fuzhou
University (grant number 022494) is gratefully acknowledged.

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10.1039/C6DT00277C

https://repository.kaust.edu.sa/bitstream/10754/605855/1/c6dt00277c.pdf

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@article{22686876e0e34e86a28f5503423c4d2c,

title = "A Class of Effective of Decarboxylative Perfluoroalkylating Reagents: [(phen)2Cu](O2CRF)",

abstract = "This article describes the invention of a class of effective reagents [(phen)2Cu](O2CRF) (1) for the decarboxylative perfluoroalkylation of aryl and heteroaryl halides. Treatment of the copper tert-butyloxide with phenanthroline ligands, with subsequent addition of perfluorocarboxylic acids afforded the air-stable copper(I) perfluorocarboxylato complexes 1. These complexes reacted with a variety of aryl and heteroaryl halides to form perfluoroalkyl(hetero)arenes in moderate to high yields. Computational studies suggested that the coordination of the second phen ligand may reduce the energy barrier for the decarboxylation of perfluorocarboxylate to facilitate the perfluoroalkylation.",

author = "Yangjie Huang and Ajitha, {Manjaly John} and Kuo-Wei Huang and Zhongxing Zhang and Zhiqiang Weng",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Financial support from the National Natural Science Foundation of China (NSFC) (grant number 21372044), the Research Fund for the Doctoral Program of Higher Education of China (grant number 20123514110003), and Fuzhou University (grant number 022494) is gratefully acknowledged.",

year = "2016",

doi = "10.1039/C6DT00277C",

language = "English (US)",

volume = "45",

pages = "8468--8474",

journal = "Dalton Trans.",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

number = "20",

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T1 - A Class of Effective of Decarboxylative Perfluoroalkylating Reagents: [(phen)2Cu](O2CRF)

AU - Huang, Yangjie

AU - Ajitha, Manjaly John

AU - Huang, Kuo-Wei

AU - Zhang, Zhongxing

AU - Weng, Zhiqiang

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Financial support from the National Natural Science Foundation of China (NSFC) (grant number 21372044), the Research Fund for the Doctoral Program of Higher Education of China (grant number 20123514110003), and Fuzhou University (grant number 022494) is gratefully acknowledged.

PY - 2016

Y1 - 2016

N2 - This article describes the invention of a class of effective reagents [(phen)2Cu](O2CRF) (1) for the decarboxylative perfluoroalkylation of aryl and heteroaryl halides. Treatment of the copper tert-butyloxide with phenanthroline ligands, with subsequent addition of perfluorocarboxylic acids afforded the air-stable copper(I) perfluorocarboxylato complexes 1. These complexes reacted with a variety of aryl and heteroaryl halides to form perfluoroalkyl(hetero)arenes in moderate to high yields. Computational studies suggested that the coordination of the second phen ligand may reduce the energy barrier for the decarboxylation of perfluorocarboxylate to facilitate the perfluoroalkylation.

AB - This article describes the invention of a class of effective reagents [(phen)2Cu](O2CRF) (1) for the decarboxylative perfluoroalkylation of aryl and heteroaryl halides. Treatment of the copper tert-butyloxide with phenanthroline ligands, with subsequent addition of perfluorocarboxylic acids afforded the air-stable copper(I) perfluorocarboxylato complexes 1. These complexes reacted with a variety of aryl and heteroaryl halides to form perfluoroalkyl(hetero)arenes in moderate to high yields. Computational studies suggested that the coordination of the second phen ligand may reduce the energy barrier for the decarboxylation of perfluorocarboxylate to facilitate the perfluoroalkylation.

UR - http://hdl.handle.net/10754/605855

UR - http://pubs.rsc.org/en/Content/ArticleLanding/2016/DT/C6DT00277C

UR - http://www.scopus.com/inward/record.url?scp=84969972308&partnerID=8YFLogxK

U2 - 10.1039/C6DT00277C

DO - 10.1039/C6DT00277C

M3 - Article

SN - 1477-9226

VL - 45

SP - 8468

EP - 8474

JO - Dalton Trans.

JF - Dalton Trans.

IS - 20

ER -

A Class of Effective of Decarboxylative Perfluoroalkylating Reagents: [(phen)2Cu](O2CRF)

Abstract

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CCDC 1427127: Experimental Crystal Structure Determination : bis(1,10-Phenanthroline)-copper heptafluorobutanoate benzene solvate

CCDC 1427126: Experimental Crystal Structure Determination : bis(1,10-Phenanthroline)-copper pentafluoropropanoate

Cite this

A Class of Effective of Decarboxylative Perfluoroalkylating Reagents: [(phen)2Cu](O2CRF)

Abstract

Bibliographical note

Access to Document

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Datasets

CCDC 1427127: Experimental Crystal Structure Determination : bis(1,10-Phenanthroline)-copper heptafluorobutanoate benzene solvate

CCDC 1427126: Experimental Crystal Structure Determination : bis(1,10-Phenanthroline)-copper pentafluoropropanoate

Cite this