Molecular dynamics and experimental investigation of rhodium recovery mechanisms from triphenylphosphine hydroxy-rhodium catalysts DOI
Xian Zhou, Lei Guo, Xiumin Chen

et al.

Separation and Purification Technology, Journal Year: 2024, Volume and Issue: 355, P. 129546 - 129546

Published: Sept. 6, 2024

Language: Английский

Reductive Coupling of P(O)–H Compounds and Aldehydes for the General Synthesis of Phosphines and Phosphine Oxides DOI
Jie Wang, Jing Xiao,

Zilong Tang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 5109 - 5117

Published: March 14, 2024

A novel strategy for the selective construction of a C(sp3)–P(III) or −P(V) bond from >P(O)–H compounds and aldehydes is disclosed. By using H3PO3/I2 system, various secondary phosphine oxides could react with both aromatic aliphatic to afford valuable phosphines (isolated as sulfides) in good yields. This method features wide substrate scope simple reaction conditions avoids use toxic halides metals.

Language: Английский

Citations

6

Phosphonium-Catalyzed Monoreduction of Bisphosphine Dioxides: Origin of Selectivity and Synthetic Applications DOI
Jing Xue, Yushan Zhang,

Zhen Huan

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(13), P. 9335 - 9346

Published: March 19, 2024

Controlling product selectivity in successive reactions of the same type is challenging owing to comparable thermodynamic and kinetic properties involved. Here, synergistic interaction two phosphoryl groups bisphosphine dioxides (BPDOs) with a bromo-phosphonium cation was studied experimentally provide practical tool for substrate–catalyst recognition. As eventual result, we have developed phosphonium-catalyzed monoreduction chiral BPDOs access an array synthetically useful monoxides (BPMOs) axial, spiro, planar chirality, which are otherwise synthesize before. The reaction features excellent impressive reactivity. It proceeds under mild conditions, avoiding use superstoichiometric amounts additives metal catalysts simplify synthetic procedure. accessibility scalability allowed rapid construction ligand library optimization asymmetric Heck-type cyclization, laying foundation broad range applications BPMOs catalysis.

Language: Английский

Citations

5

Regioselective One-Pot Synthesis of Vicinal Bisphosphine Derivatives from Nitroalkenes by Hydrophosphinylation/Elimination/Hydrophosphinylation DOI

E. Hirota,

Shin‐ichi Hirashima,

Ryuki Morita

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1797 - 1802

Published: Feb. 23, 2024

Herein, a facile method is developed for the synthesis of vicinal bisphosphine derivatives based on cascade hydrophosphinylation, elimination, and hydrophosphinylation secondary phosphine oxides with nitroalkenes. This reaction provides step-economy access to series high excellent yields (up 99%). was further extended prepare, in one-pot, regioselective that incorporated two different phosphorus functional groups.

Language: Английский

Citations

3

Combined Computational and Experimental Study Reveals Complex Mechanistic Landscape of Brønsted Acid-Catalyzed Silane-Dependent P═O Reduction DOI
Jingyang Zhang, Wang‐Yeuk Kong, Wentao Guo

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(20), P. 13983 - 13999

Published: May 13, 2024

The reaction mechanism of Brønsted acid-catalyzed silane-dependent P═O reduction has been elucidated through combined computational and experimental methods. Due to its remarkable chemo- stereoselective nature, the acid/silane system widely employed in organophosphine-catalyzed transformations involving P(V)/P(III) redox cycle. However, full mechanistic profile this type yet be clearly established date. Supported by both DFT studies, our research reveals that likely proceeds mechanisms other than accepted "dual activation mode silyl ester" or "acid-mediated direct activation" mechanism. We propose although may vary with substitution patterns silane species, acid generally activates rather group transition structures. proposed differs significantly from associated traditional C═O reduction. uniqueness originates dominant Si/O═P orbital interactions structures P/H–Si interactions. comprehensive landscape provided us will serve as a guidance for rational design development more efficient systems well novel reactions

Language: Английский

Citations

3

Palladium-catalyzed coupling of aryl sulfonium salts with [TBA][P(SiCl3)2] for the construction of tertiary phosphines DOI

Yao Chai,

Yaling Tian,

Jinhong Jia

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

We present a strategy for the synthesis of triarylphosphines via palladium-catalyzed C–P cross-coupling reactions aryl sulfonium salts with [TBA][P(SiCl 3 ) 2 ].

Language: Английский

Citations

0

Selective C(sp2)–P Cross-Coupling of Alkenylsulfonium Salts with P(O)H Compounds: Divergent Synthesis of Alkenylphosphorus Compounds DOI
Jing Xiao,

Dequan Xie,

L.‐F. WANG

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 13, 2025

Herein, we report a both regioselective and stereoselective method for the formation of C(sp2)–P bonds using alkenylsulfonium salts >P(O)–H compounds. By employing palladium catalyst or K2CO3, variety (E)-alkenylphosphorus compounds terminal alkenylphosphorus were successfully synthesized with high selectivity. Notably, trisubstituted (Z)-alkenylphosphorus first time under metal-free conditions. This protocol has wide substrate scope good functional group compatibility, providing direct highly selective approach preparation various

Language: Английский

Citations

0

Metal‐Free Formation of Xanthenes and Xanthones from 2‐aryloxybenzaldehydes via Intramolecular Cyclization DOI
Yichun Xie,

Dequan Xie,

Zhiwen Yuan

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(14)

Published: April 1, 2025

Abstract We herein report a metal‐free strategy for the selective synthesis of xanthenes and xanthones from 2‐aryloxybenzaldehydes. By employing phosphorous acid/iodine system, we achieved efficient preparation diverse via intramolecular reductive cyclization. In contrast, series were constructed same substrates through TBAI‐catalyzed direct This methodology offers notable advantages, including straightforward workup, absence metal involvement, low‐cost. A plausible reaction mechanism was also proposed.

Language: Английский

Citations

0

Tertiary Amine-Mediated Reductions of Phosphine Oxides to Phosphines DOI

Keshu Yin,

Mingjie Wei, Zhenguo Wang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5236 - 5241

Published: July 10, 2023

The reduction of phosphine oxides without the use highly reactive reductants represents a safer and more sustainable solution for recycling organophosphorus compounds. Herein, we disclose an N,N,N',N'-tetramethylethylenediamine (TMEDA)-mediated via unusual intermolecular hydride transfer. Mechanistic studies suggest that TMEDA serves as donor, while P(V) halophosphonium salt acts acceptor. This methodology provides scalable efficient protocol to reduce under mild conditions.

Language: Английский

Citations

7

Advances in Organic Reactions Using Phosphorus Acid as Reducing Agent DOI
Jing Xiao, Yichun Xie, Li‐Biao Han

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(12), P. 3702 - 3702

Published: Jan. 1, 2024

Language: Английский

Citations

2

Restoration of triphenylphosphine using the “sulfur method”: two valuable chemicals from waste products DOI
Jianqiu Zhang,

Xin Wang,

Teng Wang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(22), P. 9063 - 9068

Published: Jan. 1, 2023

Ph 3 P is found to be inert sodium in toluene even on heating.

Language: Английский

Citations

2