Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 1, 2024
Language: Английский
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
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
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
4
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
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
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
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
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
Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(12), P. 3702 - 3702
Published: Jan. 1, 2024
Language: Английский
Citations
2
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