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• W4385326482 endingPage "886" @default.
• W4385326482 startingPage "872" @default.
• W4385326482 abstract "This Award Account reports our recent studies concerning the catalytic transformations that involve a non-classical mode of molecular activation by tertiary phosphines and N-heterocyclic carbenes (NHCs). Regarding organophosphine catalysis, we successfully designed reactions based on a P(III)/P(V) redox couple. A catalytic protocol for generating pentacoordinate P(V) species was devised by the reaction of tertiary phosphines, acyl fluorides and alkynoates. The ability of the thus generated fluorophosphoranes to participate in ligand coupling and ligand metathesis with organosilicon nucleophiles enables synthetic transformations that are otherwise unattainable, including the intermolecular carbofluorination of alkynes and the hydroalkenylation of enol ethers. Regarding nucleophilic NHC catalysis, the use of imidazolium-based NHCs can generate deoxy-Breslow intermediates that are sufficiently nucleophilic to promote the aromatic substitution of aryl halides, aryl ethers and anilides. The protocol can also be used for the nucleophilic activation of styrene derivatives, allowing for the generation of a series of ylide intermediates that can serve as non-stabilized vinyl anion equivalents. These results demonstrate that synthetic transformations involving non-stabilized carbanions can be conducted under catalytic conditions without the use of strong organometallic nucleophiles. P(III)/P(V) redox catalysis is established by the generation of pentacoordinate fluorophosphorane intermediates from a tertiary phosphine, acyl fluorides and alkynoates, which can be used for catalytic carbofluorination and three component coupling reactions. N-Heterocyclic carbene catalysis is successfully applied to the activation of acrylamides and styrenes, generating highly nucleophilic ylide intermediates that can be used for catalytic nucleophilic aromatic substitution reactions." @default.
• W4385326482 created "2023-07-28" @default.
• W4385326482 creator A5001454525 @default.
• W4385326482 creator A5012396884 @default.
• W4385326482 creator A5040468597 @default.
• W4385326482 date "2023-09-15" @default.
• W4385326482 modified "2023-09-23" @default.
• W4385326482 title "Non-Classical Molecular Activation by Phosphines and N-Heterocyclic Carbenes and Its Application to Catalytic Reactions" @default.
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