Cited by ppm level Pd catalytic Suzuki-Miyaura coupling reaction in water and its application in the synthesis of Bixafen

Sustainable and Cost-Effective Suzuki–Miyaura Couplings toward the Key Biaryl Subunits of Arylex and Rinskor Active DOI

Balaram S. Takale,

Ruchita R. Thakore,

Nicholas M. Irvine

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(12), P. 4823 - 4827

Published: June 10, 2020

Challenging Suzuki–Miyaura cross couplings associated with novel crop protection active ingredients from Corteva Agriscience, Arylex and Rinskor, can be performed in water using parts per million (ppm) levels of a Pd catalyst. Each coupling required distinct set reaction conditions to achieve maximum selectivities chemical yields. By way comparison, this chemistry is not only under environmentally responsible aqueous micellar conditions, but also involves lowering loadings (3–5 times) endangered palladium than used previously attain more sustainable process.

Language: Английский

Citations

Important Role of NH-Carbazole in Aryl Amination Reactions Catalyzed by 2-Aminobiphenyl Palladacycles DOI

Raquel J. Rama, Celia Maya, Francisco Molina

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(6), P. 3934 - 3948

Published: March 7, 2023

2-Aminobiphenyl palladacycles are among the most successful precatalysts for Pd-catalyzed cross-coupling reactions, including aryl amination. However, role of NH-carbazole, a byproduct precatalyst activation, remains poorly understood. Herein, mechanism amination reactions catalyzed by cationic 2-aminobiphenyl palladacycle supported terphenyl phosphine ligand, PCyp2ArXyl2 (Cyp = cyclopentyl; ArXyl2 2,6-bis(2,6-dimethylphenyl)phenyl), P1, has been thoroughly investigated. Combining computational and experimental studies, we found that Pd(II) oxidative addition intermediate reacts with NH-carbazole in presence base (NaOtBu) to yield stable carbazolyl complex. This species functions as catalyst resting state, providing amount monoligated LPd(0) required catalysis minimizing Pd decomposition. In case reaction aniline, an equilibrium between complex on-cycle anilido analogue is established, which allows fast at room temperature. contrast, heating alkylamines, whose deprotonation involves coordination center. A microkinetic model was built combining data validate mechanistic proposals. conclusion, our study shows despite rate reduction observed some formation complex, this reduces decomposition could be considered alternative reactions.

Language: Английский

Citations

Palladium Complex Grafted on PEG-Based Amphiphilic Polymers as ppm Level Micellar Catalysts for Suzuki–Miyaura Coupling in Water DOI

Song Xiao,

Minghang Wang,

Yiming Liu

et al.

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

Published: April 14, 2025

A series of bisphosphine-grafted amphiphilic polymers based on polyethylene glycol-poly(vinylethylene glycol) (PEG-PVEG) copolymers have been synthesized by using allylic etherification polymerization as a pivotal step. Self-assembling the palladium complexes obtained into spherical micelles has investigated UV-vis, DLS and TEM analysis. The outstanding catalytic performance present micellar catalyst evidenced in aqueous Suzuki-Miyaura coupling reaction, achieving remarkable efficiency even at low loading 100 ppm within 2 h.

Language: Английский

Citations

“TPG-lite”: A new, simplified “designer” surfactant for general use in synthesis under micellar catalysis conditions in recyclable water DOI

Ruchita R. Thakore,

Balaram S. Takale, Yuting Hu

et al.

Tetrahedron, Journal Year: 2021, Volume and Issue: 87, P. 132090 - 132090

Published: March 27, 2021

Language: Английский

Citations

ppm level Pd catalytic Suzuki-Miyaura coupling reaction in water and its application in the synthesis of Bixafen DOI

Zhiyong Tan, Tingting Chen, Jiayi Shen

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134464 - 134464

Published: Jan. 1, 2025

Language: Английский

Citations