Synthesis Of Tertiary Phosphines Research Articles

Synthesis of Triarylphosphines via Cu-Catalyzed Coupling of Aryl Halides and Acylphosphines

AbstractA Cu-catalyzed C(sp2)–P bond forming reaction using an acylphosphine as the phosphorus source is reported; with CuCl2 as the catalyst, 34 examples of aryl iodides and bromides were converted into triarylphosphines in good to excellent yield. A preliminary study of the mechanism was carried out and found that a radical intermediate is not involved. This reaction is an extension of the application of acylphosphines in Cu-catalyzed reactions and shows their potential as a phosphination reagent in the synthesis of tertiary phosphines.

Electrochemical oxidative N-H/P-H cross-coupling with H2 evolution towards the synthesis of tertiary phosphines.

Tertiary phosphines(iii) find widespread use in many aspects of synthetic organic chemistry. Herein, we developed a facile and novel electrochemical oxidative N–H/P–H cross-coupling method, leading to a series of expected tertiary phosphines(iii) under mild conditions with excellent yields. It is worth noting that this electrochemical protocol features very good reaction selectivity, where only a 1 : 1 ratio of amine and phosphine was required in the reaction. Moreover, this electrochemical protocol proved to be practical and scalable. Mechanistic insights suggested that the P radical was involved in this reaction.

CsOH-Promoted P-Alkylation: A Convenient and Highly Efficient Synthesis of Tertiary Phosphines.

A mild and efficient method for the synthesis of tertiary phosphines and ditertiary phosphines has been developed. In the presence of cesium hydroxide, molecular sieves and DMF at room temperature, various secondary phosphines and alkyl bromides were examined, and the results have demonstrated that this methodology offers a general synthetic procedure to produce tertiary phosphines in moderate to high yields. Optically active tertiary phosphine synthesis is also described.

ChemInform Abstract: Synthesis of Tertiary Phosphines with 2‐Alkenyl Groups.

ChemInform Abstract: Synthesis of Tertiary Phosphines with 2‐Alkenyl Groups.

New Asymmetric Synthesis of Tertiary Phosphines via Phosphinous Complexes

Abstract Asymmetric syntheses of phosphinous complexes and tertiary phosphines were described by Regioselective P—O bond cleavage of diastereomerically pure oxazaphospholidine W(CO)5 or BH3 complexes.

ChemInform Abstract: Synthesis of Tertiary Phosphines, e.g. (III), (VIII), (XII), and Phosphine Oxides, e.g. (VI), (X), (XIII), (XIV), by Nucleophilic Addition Reaction Applying Phase‐Transfer Catalysts or a Superbasic Medium.

ChemInform Abstract: Synthesis of Tertiary Phosphines, e.g. (III), (VIII), (XII), and Phosphine Oxides, e.g. (VI), (X), (XIII), (XIV), by Nucleophilic Addition Reaction Applying Phase‐Transfer Catalysts or a Superbasic Medium.

Organophosphorus compounds—V a new synthesis of tertiary phosphines and arsines, phosphonic and thiophosphonic as well as phosphinic and thiophosphinic halides

The alkylation of dialkylhalophosphines and arsines with organic lead compounds produces in excellent yields tertiary phosphines and arsines. Since the alkylation can be done stepwise, this represents a simple method for the preparation of tertiary phosphines and arsines containing three different organic groups. Furthermore, phosphoryl and thiophosphoryl halides can also be alkylated and arylated with organic lead and tin compounds to give phosphonic, phosphinic, thiophosphonic, and thiophosphinic halides, respectively. Aminophosphines, phosphite and phosphate esters do not react with organic lead compounds even upon extensive heating at high temperatures.