Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
The direct transformation of alkylboron has emerged as a versatile and powerful methodology for creating carbon-carbon and carbon-heteroatom bonds. However, its potential application in the formation of carbon and phosphorus remains unexplored. In this study, we present an alkoxide base-promoted reaction system that enables deborylative phosphination of benzylic organoboronates and geminal bis(boronates) via selective C-B bond cleavage. This approach allows for the synthesis of valuable tertiary phosphines in good yields under mild conditions. The practicality and industrial potential of this approach are underscored by the operational simplicity, broad substrate scope, and easy scalability.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.4c00001 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Iron-Catalyzed Asymmetric Reductive Cross-Coupling of Ketimines with Alkyl Iodides.
J Am Chem Soc
August 2025
Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, P. R. China.
We report herein an Fe-catalyzed asymmetric reductive cross-coupling of carbonyl-containing ketimines with unactivated alkyl halides, enabling the efficient synthesis of enantioenriched α-tertiary amino esters and amides. This transformation is promoted by a commercially available iron(II) triflate catalyst in combination with a chiral bisoxazoline-phosphine (NPN) ligand and inexpensive manganese as the reductant. A broad range of primary and secondary alkyl iodides are compatible, affording the desired products in high yields with excellent enantioselectivities and exceptional functional group tolerance.
View Article and Find Full Text PDFBioinspired Peptide-Phosphonium Salt Catalysis Unlocks Asymmetric Desymmetrization of Phosphoryl Acids: Programmable Synthesis of P(V)-Stereogenic Molecules.
Angew Chem Int Ed Engl
August 2025
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064, P.R. China.
Enantioselective desymmetrization of prochiral phosphorus(V) compounds represents a pivotal strategy for constructing P(V)-stereogenic skeletons, yet existing methods face limitations in structural diversification and metal-free catalytic systems. Here we disclose that a bioinspired peptide-phosphonium salt (PPS) catalytic system successfully enables precise desymmetrization of phosphinic acids through synergistic ion-pairing and hydrogen-bonding interactions. This strategy affords multifunctional platform molecules bearing P(V)-stereocenters with excellent enantiocontrol and broad compatibility (43 examples, up to 92% yield, up to >99% ee) at very low catalyst loading (1 mol%).
View Article and Find Full Text PDFPhotocatalytic Asymmetric Oxidation of Phosphines with Water.
J Am Chem Soc
August 2025
Pingyuan Laboratory, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
P-chiral tertiary phosphine oxides (TPOs) hold significant synthetic value due to their capacity to serve as versatile precursors for a wide range of valuable P-chiral phosphorus-containing compounds. However, the direct asymmetric oxidation of readily available phosphines into these TPOs remains a substantial challenge, as no efficient and practical methods have been reported to date. In this study, we present the first catalytic asymmetric approach to access P-chiral TPOs through a photoredox-mediated radical process.
View Article and Find Full Text PDFAsymmetric (4 + 2) Cyclization of γ-Substituted Propargyl Carboxylates with -Quinone Methides Catalyzed by Chiral Tertiary Phosphine.
Org Lett
August 2025
Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China.
An enantioselective (4 + 2) cycloaddition reaction of γ-aryl-substituted alkynyl carboxylates with -quinone methides (-QMs) was developed for the first time in the catalysis of (,)-DIPAMP. A series of chiral 4H-chromenes derivatives were available in good yields (62%-89% yield) and excellent enantioselectivities (up to 96% enantiomeric excess). Those obtained products could be further transformed to other derivatives.
View Article and Find Full Text PDFThe mechanism by which Pd precursors are reduced to catalytically active low-valent Pd species has been a subject of interest for developing better catalysts. This process is well understood for catalytic systems employing a combination of palladium(ii) acetate [Pd(OAc)] and tertiary phosphines. However, the mechanism of reduction of palladium(ii) acetylacetonate [Pd(acac)] in the presence of phosphines has not been thoroughly investigated.
View Article and Find Full Text PDF