Lanthanide amides [(Me3Si)2N]3Ln(µ-Cl)Li(THF)3-catalyzed phospho-aldol-brook rearrangement reaction of dialkyl phosphites with isatins

2012 ◽  
Vol 23 (5) ◽  
pp. 449-456 ◽  
Author(s):  
Lu Wang ◽  
Zhigang Yao ◽  
Fan Xu ◽  
Qi Shen
Keyword(s):  
Brook Rearrangement ◽  
Rearrangement Reaction ◽  
Dialkyl Phosphites

scholarly journals DBU Catalyzed Phospho-Aldol-Brook Rearrangement for Rapid Preparation of α-Phosphates Amide in Solvent-Free Conditions

Catalysts ◽  
2020 ◽  
Vol 10 (12) ◽  
pp. 1445
Author(s):  
Shunhong Chen ◽  
Shengxin Guo ◽  
Feng He ◽  
Yingxia Zhang ◽  
Zengxue Wu ◽  
...  
Keyword(s):  
Room Temperature ◽  
Solvent Free ◽  
The Novel ◽  
Rapid Preparation ◽  
Good Tolerance ◽  
Amide Derivatives ◽  
Solvent Free Conditions ◽  
Brook Rearrangement ◽  
Rearrangement Reaction ◽  
Dialkyl Phosphites

The 1,8-diazabicyclo [5.4.0] undec-7-ene DBU-catalyzed Phospho-Aldol-Brook Rearrangement reaction of α-ketoamide and dialkyl phosphites was developed under solvent-free at room temperature. The novel α-Phosphate Amide derivatives could be obtained with good yield (86–96%), which also exhibited good tolerance of various dialkyl phosphites and α-ketoamide, including isatins. In addition, the reaction was conducted in both gram-scale and mol-scale, and the title compounds could also be obtained in excellent yield (more than 91%) within 5 min.

scholarly journals Organic Base Catalyzed Cascade Phospho-Aldol-Brook Rearrangement Reaction of Isatins with H-phosphonates

2014 ◽  
Vol 34 (6) ◽  
pp. 1177 ◽  
Author(s):  
Wei Fang ◽  
Guogui Liu ◽  
Xiaofei Huang ◽  
Jun Jia ◽  
Xingwang Wang
Keyword(s):  
Organic Base ◽  
Brook Rearrangement ◽  
Rearrangement Reaction

scholarly journals Research Progress in [1,2]-Phospha-Brook Rearrangement Reaction

Daxue Huaxue ◽  
2020 ◽  
Vol 0 (0) ◽  
pp. 1-0
Author(s):  
Xiyuan Zhang ◽  
Yuming Li ◽  
Zhiwei Miao
Keyword(s):  
Research Progress ◽  
Brook Rearrangement ◽  
Rearrangement Reaction

scholarly journals MS 4A-Promoted Aqueous Phospho-Aldol-Brook Rearrangement Reaction of Isatins

Heterocycles ◽  
2022 ◽  
Vol 104 (1) ◽  
pp. 159
Author(s):  
Takeshi Oriyama ◽  
Wei Han ◽  
Fan Liu
Keyword(s):  
Brook Rearrangement ◽  
Rearrangement Reaction

Mechanistic investigation on N → Cα → O relay via non-Brook rearrangement: reaction conditions promote synthesis of furo[3,2-c]pyridinones

2017 ◽  
Vol 15 (43) ◽  
pp. 9127-9138 ◽  
Author(s):  
Lihan Zhu ◽  
Haiyan Yuan ◽  
Jingping Zhang
Keyword(s):  
Dft Calculations ◽  
Reaction Conditions ◽  
Mechanistic Investigation ◽  
Brook Rearrangement ◽  
Rearrangement Reaction

DFT calculations disclosed the effect of reaction conditions on the effective anion relay sequence of a NaH promoted non-Brook rearrangement.

Synthesis, Structure and Reactivities of Pentacoordinated Phosphorus–Boron Bonded Compounds

2020 ◽  
Author(s):  
Nathan O'Brien ◽  
Naokazu Kano ◽  
Nizam Havare ◽  
Ryohei Uematsu ◽  
Romain Ramozzi ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Ring Expansion ◽  
Bicyclic Compound ◽  
Compound A ◽  
Ligand System ◽  
Large Bulk ◽  
Rearrangement Reaction ◽  
Hydride Abstraction ◽  
Pentacoordinated Phosphorus ◽  
Acids And Bases

<div>The isolation and reactivities of two pentacoordinated phosphorus–tetracoordinated boron bonded compounds were</div><div>explored. A strong Lewis acidic boron reagent and electron-withdrawing ligand system were required to form the</div><div>pentacoordinated phosphorus state of the P–B bond. The first compound, a phosphoranyl-trihydroborate, gave a THF</div><div>stabilised phosphoranyl-borane intermediate upon a single hydride abstraction in THF. This compound could undergo a</div><div>unique rearrangement reaction, that involved a two-fold ring expansion, to give an unusual fused bicyclic compound or it</div><div>could act as a mono-hydroboration reagent. The hydroboration reactivity of the intermediate was found to be more reactive</div><div>towards alkynes over alkenes with good to moderate regioselectivity towards the terminal carbon. The second compound,</div><div>a phosphoranyl-triarylborate, was found to have a vastly different reactivity to the trihydroborate as it was highly stable</div><div>towards acids and bases. This is thought to be due to the large bulk around the P–B bond as shown in the crystal structure</div>

Synthesis of Phosphonates, Phosphinates and Tertiary Phosphine Oxides by Pd- or Ni-Catalyzed Microwave-Assisted P–C Coupling Reactions without the Addition of Conventional Ligands

2021 ◽  
Vol 25 ◽  
Author(s):  
Réka Henyecz ◽  
György Keglevich
Keyword(s):  
Tautomeric Form ◽  
Catalyst Precursor ◽  
Coupling Reactions ◽  
Optimum Conditions ◽  
Pd Catalysts ◽  
Catalyst Complex ◽  
Two Factors ◽  
Dialkyl Phosphites ◽  
Catalyst Systems ◽  
P Ligands

Abstract: Microwave (MW)-assistance may be a powerful tool also in the Hirao P–C coupling reactions of vinyl/aryl halides with dialkyl phosphites in the presence of Pd-catalysts/P-ligands elaborated forty years ago. This review surveys the development of this reaction by showing the expansion of the reagents and catalysts, as well as the information accumulated. The stress was laid on the “green” aspects, the simplification of the catalyst systems, and the reliable mechanistic details in order to be able to establish the optimum conditions. The best protocol involves the use of some excess of the >P(O)H reagent to ensure the PdII→Pd0 reduction and, via its trivalent tautomeric form (>POH) also the P-ligand. The overall rate is the result of two factors, the activity of the catalyst complex formed, and the reactivity of the reactants in the P–C coupling reactions. Both components are influenced by the nature of the aryl substituents in Ar2P(O)H. NiII salts may also be used as the catalyst precursor, however, despite the PdII→Pd0→PdII route, in this case, a NiII→NiIV→NiII sequence was proved.

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