Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles

Martí Garçon; Clare Bakewell; Andrew J.P. White; Mark R. Crimmin

doi:10.1039/c8cc09701a

Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles

Martí Garçon, Clare Bakewell, Andrew J.P. White, Mark R. Crimmin^*

^*Corresponding author for this work

Chemistry

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

16 Citations (Scopus)

Abstract

The reaction of a metal complex containing a polar Fe-Mg bond with 2-(pentafluorophenyl)pyridine leads to selective C-F bond activation. A stepwise S_NAr mechanism involving attack of the bimetallic nucleophile on the electron-deficient aromatic ring has been identified by DFT calculations. Despite the long and rich history of metal anions in organic synthesis, this is the first time the S_NAr mechanism has been elucidated in detail for metal-based nucleophiles.

Original language	English
Pages (from-to)	1805-1808
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	12
DOIs	https://doi.org/10.1039/c8cc09701a
Publication status	Published - 2019

Access to Document

10.1039/c8cc09701a

Cite this

@article{e1477e6e4cc6439c82ad96a34b82c4a3,

title = "Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles",

abstract = "The reaction of a metal complex containing a polar Fe-Mg bond with 2-(pentafluorophenyl)pyridine leads to selective C-F bond activation. A stepwise SNAr mechanism involving attack of the bimetallic nucleophile on the electron-deficient aromatic ring has been identified by DFT calculations. Despite the long and rich history of metal anions in organic synthesis, this is the first time the SNAr mechanism has been elucidated in detail for metal-based nucleophiles.",

author = "Mart{\'i} Gar{\c c}on and Clare Bakewell and White, {Andrew J.P.} and Crimmin, {Mark R.}",

note = "Publisher Copyright: {\textcopyright} 2019 The Royal Society of Chemistry.",

year = "2019",

doi = "10.1039/c8cc09701a",

language = "English",

volume = "55",

pages = "1805--1808",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "12",

}

TY - JOUR

T1 - Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles

AU - Garçon, Martí

AU - Bakewell, Clare

AU - White, Andrew J.P.

AU - Crimmin, Mark R.

PY - 2019

Y1 - 2019

N2 - The reaction of a metal complex containing a polar Fe-Mg bond with 2-(pentafluorophenyl)pyridine leads to selective C-F bond activation. A stepwise SNAr mechanism involving attack of the bimetallic nucleophile on the electron-deficient aromatic ring has been identified by DFT calculations. Despite the long and rich history of metal anions in organic synthesis, this is the first time the SNAr mechanism has been elucidated in detail for metal-based nucleophiles.

AB - The reaction of a metal complex containing a polar Fe-Mg bond with 2-(pentafluorophenyl)pyridine leads to selective C-F bond activation. A stepwise SNAr mechanism involving attack of the bimetallic nucleophile on the electron-deficient aromatic ring has been identified by DFT calculations. Despite the long and rich history of metal anions in organic synthesis, this is the first time the SNAr mechanism has been elucidated in detail for metal-based nucleophiles.

UR - http://www.scopus.com/inward/record.url?scp=85061145687&partnerID=8YFLogxK

U2 - 10.1039/c8cc09701a

DO - 10.1039/c8cc09701a

M3 - Article

C2 - 30667423

AN - SCOPUS:85061145687

SN - 1359-7345

VL - 55

SP - 1805

EP - 1808

JO - Chemical Communications

JF - Chemical Communications

IS - 12

ER -

Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles

Abstract

Access to Document

Other files and links

Fingerprint

Cite this