Triphenylphosphine reacts with organic azide compounds to form iminophosphorane
Deoxygenation Reactions
Triphenylphosphine is widely used in the reduction of hydrogen peroxide or endoperoxides.
The reaction is substrate dependent and can result in alcohols, carbonyl compounds or epoxides. The main driving force for these reactions is the ability of triphenylphosphine to form strong P=O bonds with relatively weak O-O bonds (188-209 kJ/mol). For example, triphenylphosphine can be utilized to reductively decompose ozonides, selectively prepare ketones and aldehydes
Reaction with azides [Staudinger reduction].
Triphenylphosphine reacts with organic azides to form iminophosphorane.
Iminophosphorane is a more active nucleophilic reagent, easy to react with electrophilic reagents. For example, it reacts with aldehydes and ketones to form imines and triphenylphosphine oxides. This reaction is similar to the Wittig reaction and is called the aza-Wittig reaction, which is also driven by the formation of triphenylphosphine oxide
Reaction with organic sulfides [Eschenmoser desulfurization reaction
At room temperature triphenylphosphine can convert cyclic sulfur compounds to olefins
Dehalogenation reaction
α-Bromo ketone reacts with triphenylphosphine to form ketone
Reactions with organic epoxides
Refluxing in water and acetone solvents, triphenylphosphine can convert epoxides to cycloimines with the participation of sodium azide
Preparation of substituted pyrroles
The reaction of aniline, furandione with triphenylphosphine produces -phenyl-pyrrolidinedione
As a ligand for metal catalysts [Summary of metal-catalyzed reactions
It acts as a ligand with many transition metals to form a metal catalyst, which is an important catalyst [8], commonly used to catalyze the coupling reaction, an important method to construct carbon-carbon bonds, characterized by mild catalytic conditions. Phenylboronic acid reacts directly with aromatic halogenated hydrocarbons to form biphenyl analogs, and the yield of this reaction reaches 90% In addition to phenylboronic acid and halogenated compounds, magnesium reagents, zinc reagents, tin reagents, and silica compounds can be used as substrates for the coupling reaction.
Preparation of halogenated compounds [Appel reaction
The Appel reaction was utilized to convert alcohols to halogenated substances.
Iodination reaction of triphenylphosphine/imidazole/iodine system
Preparation of aliphatic bromo-substituents using triphenylphosphine bromide
Preparation of amides [Preparation of amides by triphenylphosphine-based condensates
Mitsunobu reaction
Reaction in which the SN2 reaction configuration is flipped to obtain a substitution product of opposite configuration using an azodicarboxylic acid ester (usually diethyl azodicarboxylate, DEAD) and a trisubstituted phosphine compound (usually triphenylphosphine), a nucleophilic reagent, and an alcohol.
