Elsevier eBooks, Journal Year: 2023, Volume and Issue: unknown
Published: Jan. 1, 2023
Language: Английский
Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(3), P. 420 - 425
Published: Dec. 20, 2023
Abstract A strategy was developed for synthesizing furan‐fused dibenzotropones via intramolecular Wittig reactions of alkylidene dibenzo‐ β ‐tropolones and acylating reactants in catalytic or stoichiometric conditions. With these protocols, a series furo[2,3‐ f ]dibenzotropones were obtained 49–99% yields within 1–10 hours. Mechanistic studies the base‐free phenomena revealed that organophosphane acts both as mediator regenerable Brønsted base under heating.
Language: Английский
Citations
6
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(4), P. 733 - 739
Published: Jan. 15, 2024
Abstract The synthesis of a difunctional P‐heterocycle combining phosphonate and ester moieties in six‐membered ring is described. Using trifluoromethane sulfonic acid HOTf as organocatalyst, ring‐opening with neopentyl alcohol readily occurs complete selectivity for O‐acyl bond cleavage. In turn, polymerization proceeds controlled manner when an excess used. Copolymerization ϵ‐caprolactone also reported semi‐batch conditions are shown to enable regular incorporation the along polymer chains.
Language: Английский
Citations
1
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15851 - 15863
Published: Oct. 19, 2024
A set of structurally analogous, albeit electronically distinct, phosphamides (1aa-10aa) is prepared, and the effect electronic amendment due to p-substitution has been tested for conversion alcohols halides via Appel reaction. The −OMe-substituted diphosphamide (8aa) remains most active, providing ∼96% with a TON 11 in moderate reaction conditions large substrate scope. Halide formation follows pseudo-first-order rate constant (kobs) 7.13 × 10–5 s–1. Temp-dependent kinetics Eyring analyses reveal activation parameters ΔH‡ 28.95 (±1.6) kcal mol–1, ΔS‡ −70.02 (±0.4) cal K–1 ΔG‡298 49.81 (±1.2) mol–1. deuterium labeling study highlights O–H dissociation alcohol as rate-determining step, while Hammett analysis p-substituted benzyl indicates positive charge accumulation at phosphorus center during HOMO–LUMO energy NPA show that p–OMe substitutions 8aa make "P═O" bond more ionic corresponding aminophosphine nucleophilic, which are favorable In situ detection salt, [R3PX]CX3 alkoxy phosphonium cation [R3POR]X, validates pathway mediated by phosphamides.
Language: Английский
Citations
1
Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: unknown
Published: Nov. 1, 2023
Herein, we reported an efficient and straightforward method to realize desaturated β-C(sp3)-H sulfonylation phosphonylation of cyclic amines driven by electrochemistry using catalytic amounts CP2Fe as the redox mediator. This protocol which had good functional group compatibility, provided desired enaminyl sulfone phosphine oxide products with high chemo- regio-selectivity under mild conditions. Several mechanistic studies have suggested that underwent multiple single-electron oxidation deprotonation processes, followed a capture step involving either sulfonyl radical or phosphonyl radical, ultimately leading products.
Language: Английский
Citations
3
Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(15), P. 3732 - 3740
Published: Jan. 1, 2023
Diphosphine ligands are highly popular but costly toolkit in organic chemistry.
Language: Английский
Citations
2
Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown
Published: Aug. 11, 2024
Abstract Trivalent phosphine catalysis is mostly utilized to activate the carbon‐carbon multiple bonds form carbanion intermediate species and highly sensitive certain variables. Random manual multi‐variables are critical for understanding batch disabled regeneration of trivalent chemistry. We need artificial intelligence‐based system which can change variable based on previously conducted failed experiment. Herein, we report an auto‐optimized electro‐micro‐flow reactor platform in‐situ reduction stable P(V) oxide P(III) further method Corey‐Fuchs reaction.
Language: Английский
Citations
0
Symmetry, Journal Year: 2024, Volume and Issue: 16(8), P. 976 - 976
Published: Aug. 1, 2024
This paper presents the efficient reduction of phosphinoylacetic acid esters and 3-phosphorylated coumarin to their corresponding phosphino-boranes using BH₃-THF complexes. Optimized conditions for resulted in high yields phosphinoborates. The straightforwardness efficiency process were demonstrated diarylphosphinoylacetic ethyl esters, as well P-stereogenic L-menthyl where simultaneous strong P=O bond ester group was exclusively observed first time. study also highlighted significant influence steric effects with bulky substituents, such menthol or 1-naphthyl substituent at phosphorus, on efficiency. However, coumarins produced an unexpected reaction product: a 2,3-dihydrobenzofuran derivative. present findings provide valuable information direct phosphine oxides related compounds, demonstrating versatility borane complexes synthetic chemistry, new perspectives studying problems symmetry asymmetry chemistry transformations.
Language: Английский
Citations
0
Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 1, 2024
Language: Английский
Citations
0
Elsevier eBooks, Journal Year: 2023, Volume and Issue: unknown
Published: Jan. 1, 2023
Language: Английский
Citations
0