[reaction: see text] A general new method for the one-pot preparation of secondary phosphines 11 and in situ generation of their borane complexes 12 is described. This method consists of the sequential addition, at room temperature, of equivalent amounts of R(1)MgBr and R(2)MgBr to 1 equiv of the phosphorus atom donor reagent 1. Final treatment with water gives secondary phosphines R(1)R(2)PH (or the corresponding phosphine-borane complexes if treated with BH(3).THF) and the end product 6, which can be recycled.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol060284dDOI Listing

Publication Analysis

Top Keywords

secondary phosphines
12
borane complexes
8
donor reagent
8
high atom-economical
4
atom-economical one-pot
4
one-pot synthesis
4
synthesis secondary
4
phosphines borane
4
complexes recycling
4
recycling phosphorus
4

Similar Publications

In this study, phosphoramide compounds were successfully synthesized a series of reaction transformations from P(O)H compounds. The process began with the formation of P-Se-Ar bonds, facilitated by the synergistic effect of phenylboronic acid, selenium, and appropriate ligands in the presence of copper. Following this, nucleophilic substitution reactions with amine compounds were conducted to create P-N bonds.

View Article and Find Full Text PDF

Base promoted regio- and stereoselective hydrophosphinylation of allenes.

Org Biomol Chem

December 2024

Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361001, Fujian, People's Republic of China.

A novel and transition-metal-free hydrophosphinylation of allenes with secondary phosphine oxides was developed. In the presence of the cheap and commercially available cesium carbonate, various hydrophosphinylation products were synthesized with exclusive regio- and stereoselectivity under mild conditions. This methodology provides simple and efficient access to ()-alkenylphosphine oxides in moderate to excellent yields with a relatively broad substrate scope.

View Article and Find Full Text PDF

The synthesis of a novel phosphine-based pincer chromium(II) complex CrCl(PONN) (Cr-1) is reported in this study. The complex exhibited promising catalytic performance in C-C and C-N bond formation using the borrowing hydrogen methodology. Cr-1 catalyzed the α-alkylation of ketones using primary alcohols as alkyl surrogates in the presence of catalytic amount of a base.

View Article and Find Full Text PDF

Palladium-Catalyzed Coupling of Aryl Chlorides with Secondary Phosphines to Construct Unsymmetrical Tertiary Phosphines.

Org Lett

December 2024

School of Chemistry and Chemical Engineering, Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, Guangxi University, Nanning 530004, Guangxi, P. R. China.

The functionalization of the C-Cl bond in unactivated aryl chlorides under mild conditions presents a significant challenge. We disclose a general protocol for constructing both partially and entirely unsymmetrical tertiary phosphines through the Pd/keYPhos-catalyzed coupling of aryl chlorides with secondary phosphines under mild conditions. The reaction exhibits excellent functional group tolerance and broad substrate scopes.

View Article and Find Full Text PDF

Quantifying Lewis acidity is essential for understanding and optimizing the performance of Lewis acids in diverse applications. Next to the widely accepted Gutmann-Beckett (GB) method, using triethyl phosphine oxide (TEPO) as a probe, the Childs method-employing trans-crotonaldehyde (TCA)-gained attention as an NMR-based technique for measuring effective Lewis acidity (eLA). Despite its steady use, the robustness of Childs method and its correlation with other measures remain underexplored.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!