The palladium-catalyzed hydroesterification reaction was performed with polyols and olefins in a liquid/liquid biphasic system composed of unreacted polyol on the one hand and apolar reaction products/organic solvents on the other hand. The palladium-based catalyst was immobilized in the polyol phase thanks to the use of cationic triarylphosphines possessing pendent protonated amino groups in the acidic reaction medium or to the sulfonated phosphine TPPTS (trisodium triphenylphosphine-3,3',3''-trisulfonate). Owing to the insolubility of the products in the catalytic phase, this approach allowed the synthesis of monoesters of polyols with high selectivities as well as the easy separation of the catalyst through simple decantation.

Download full-text PDF

Source
http://dx.doi.org/10.1002/cssc.201403397DOI Listing

Publication Analysis

Top Keywords

palladium-catalyzed hydroesterification
8
polyol phase
8
biphasic palladium-catalyzed
4
hydroesterification polyol
4
phase selective
4
selective synthesis
4
synthesis derived
4
derived monoesters
4
monoesters palladium-catalyzed
4
hydroesterification reaction
4

Similar Publications

Regioselective hydroesterification of alkenes and alkenylphenols utilizing CO and hydrosilane.

Chem Sci

May 2023

State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian National Laboratory for Clean Energy Dalian 116023 China

As an important and attractive C1 building block, the diversified exploitation of CO in chemical transformations possesses significant research and application value. Herein, an effective palladium-catalyzed intermolecular hydroesterification of a wide range of alkenes with CO and PMHS is described, successfully generating diverse esters with up to 98% yield and up to 100% linear-selectivity. In addition, the palladium-catalyzed intramolecular hydroesterification of alkenylphenols with CO and PMHS is also developed to construct a variety of 3-substituted-benzofuran-2(3)-ones with up to 89% yield under mild conditions.

View Article and Find Full Text PDF

Palladium-catalyzed linear-selective hydroesterification of vinyl arenes with alcohols enabled by diphosphine ligands derived from bis[2-(diphenylphosphino)ethyl]amides has been developed. A variety of 3-arylpropanoate esters were obtained in high yields and regioselectivity. The robustness of this methodology was further demonstrated by the efficient gram-scale synthesis of the ethyl 3-phenylpropanoate as a precursor to hydrocinnamic acid.

View Article and Find Full Text PDF

Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates.

Org Lett

November 2021

Chang-Kung Chuang Institute, and Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P. R. China.

A palladium-catalyzed asymmetric hydroesterification of α-aryl acrylic acids with CO and alcohol was developed, preparing a variety of chiral α-substituted succinates in moderate yields with high values. The kinetic profile of the reaction progress revealed that the alkene substrate first underwent the hydroesterification followed by esterification with alcohol. The origin of the enantioselectivity was elucidated by density functional theory computation.

View Article and Find Full Text PDF

Enantioselective Hydroesterificative Cyclization of 1,6-Enynes to Chiral γ-Lactams Bearing a Quaternary Carbon Stereocenter.

Org Lett

May 2021

Chang-Kung Chuang Institute, and Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P.R. China.

A palladium-catalyzed asymmetric hydroesterification-cyclization of 1,6-enynes with CO and alcohol was developed to efficiently prepare a variety of enantioenriched γ-lactams bearing a chiral quaternary carbon center and a carboxylic ester group. The approach featured good to high chemo-, region-, and enantioselectivities, high atom economy, and mild reaction conditions as well as broad substrate scope. The correlation between the multiple selectivities of such process and the -substitutes of the amide linker in the 1,6-enyne substrate has been depicted by the crystallographic evidence and control experiments.

View Article and Find Full Text PDF

A class of novel diphosphine ligands bearing pyridine substituents was designed and synthesized for the first time. The resulting palladium complexes of L1 allow for chemo- and regioselective dialkoxycarbonylation of various aromatic and aliphatic alkynes affording a wide range of 1,4-dicarboxylic acid diesters in high yields and selectivities. Kinetic studies suggest the generation of 1,4-dicarboxylic acid diesters via cascade hydroesterification of the corresponding alkynes.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!