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SNAr catalysis enhanced by an aromatic donor-acceptor interaction; facile access to chlorinated polyfluoroarenes.

ABSTRACT: Selective catalytic SNAr reaction of polyfluoroaryl C-F bonds with chloride is shown. Stoichiometric TMSCl makes the reaction exergonic and allows catalysis, which involves ground state elevation of chloride, aromatic donor-acceptor interactions, and stabilization of the Meisenheimer complex. Traditional cross-coupling of the products is now possible and demonstrates the utility.

SUBMITTER: Senaweera S

PROVIDER: S-EPMC5549941 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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SNAr catalysis enhanced by an aromatic donor-acceptor interaction; facile access to chlorinated polyfluoroarenes.

Senaweera Sameera S Weaver Jimmie D JD

Chemical communications (Cambridge, England) 20170701 54

Selective catalytic SNAr reaction of polyfluoroaryl C-F bonds with chloride is shown. Stoichiometric TMSCl makes the reaction exergonic and allows catalysis, which involves ground state elevation of chloride, aromatic donor-acceptor interactions, and stabilization of the Meisenheimer complex. Traditional cross-coupling of the products is now possible and demonstrates the utility. ...[more]

PMID: 28634609

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