Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles | Zendy

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

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Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles

Author(s) -

Martí Garçon,

Clare Bakewell,

Andrew J. P. White,

Mark R. Crimmin

Publication year - 2019

Publication title -

chemical communications

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.837

H-Index - 333

eISSN - 1364-548X

pISSN - 1359-7345

DOI - 10.1039/c8cc09701a

Subject(s) - nucleophile , chemistry , pyridine , bimetallic strip , nucleophilic substitution , substitution reaction , nucleophilic aromatic substitution , polar , medicinal chemistry , computational chemistry , organic chemistry , catalysis , physics , astronomy

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.

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