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Taming Bronsted Acid Reactivity: Nucleophilic Substitutions of Propargylic Alcohols with N-Nucleophiles Mediated by Phosphorus-Based Bronsted Acid Catalysts.

ABSTRACT: The activity of diethyl phosphite and diphenyl phosphate in propargylation reactions with N-nucleophiles of varying basicity is presented. A careful choice of the reaction conditions minimized undesired rearrangements and arylation processes, typical side reactions with Brønsted acid catalysis. These systems are compatible with technical solvents and presence of air, and they are also applicable to C-, O-, and S-nucleophiles.

SUBMITTER: Radtanajiravong L

PROVIDER: S-EPMC6682045 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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Taming Brønsted Acid Reactivity: Nucleophilic Substitutions of Propargylic Alcohols with N-Nucleophiles Mediated by Phosphorus-Based Brønsted Acid Catalysts.

Radtanajiravong Lalita L Díez-González Silvia S

ACS omega 20190718 7

The activity of diethyl phosphite and diphenyl phosphate in propargylation reactions with N-nucleophiles of varying basicity is presented. A careful choice of the reaction conditions minimized undesired rearrangements and arylation processes, typical side reactions with Brønsted acid catalysis. These systems are compatible with technical solvents and presence of air, and they are also applicable to C-, O-, and S-nucleophiles. ...[more]

PMID: 31460347

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