Cai-Sheng Song

Silica-supported bidentate arsine palladium(0) complex: a highly active and stereoselective catalyst for arylation of conjugated alkenes

A silica-supported bidentate arsine palladium(0) complex has been prepared from 4-oxa-6,7-dichloroheptyltriethoxysilane via immobilization on fumed silica, followed by reacting with potassium diphenylarsenide and palladium chloride, and then the reduction with hydrazine hydrate. The complex has been characterized by X-ray photoelectron spectroscopy and it is a highly active and stereoselective catalyst for arylation of styrene and acrylic acid with aryl halides affording a variety of trans-stilbenes and substituted trans-cinnamic acids in high yields.

Synthesis of silica-supported poly-γ-diphenylarsinopropylsiloxane palladium complex and its catalytic behavior for Heck carbonylation of aryl halides

A silica-supported poly-γ-diphenylarsinopropylsiloxane palladium complex has been prepared from γ-chloropropyltriethoxysilane via immobilization on fumed silica, followed by reacting with potassium diphenylarsenide in THF and then the reaction with palladium chloride. It is an efficient catalyst for Heck carbonylation of aryl halides under atmospheric pressure of carbon monoxide. This polymeric palladium catalyst can be recovered and reused.

FORMYLATION OF ARYL HALIDES CATALYZED BY A SILICA-SUPPORTED PHOSPHINE PALLADIUM COMPLEX

ABSTRACT The formylation of aryl bromides or iodides with sodium formate at atmospheric pressure of carbon monoxide readily proceeded in the presence of a silica-supported phosphine palladium complex in DMF to give the corresponding aldehydes in moderate to good yields.

PALLADIUM-CATALYZED ARYLATION OF ALLYLIC ALCOHOLS WITH ARYL IODIDES IN WATER

Palladium-catalyzed arylation of allylic alcohols with aryl iodides are shown to occur in the presence of sodium bicarbonate and tetra-n-butylammonium chloride in pure water using palladium acetate as catalyst. β-aromatic carbonyl compounds are obtained in good yields.

Selenium-Linking Strategy for Traceless Solid-Phase Synthesis of Acrylamides

Abstract A novel polystyrene-supported β-selenopropionic acid has been developed and applied to simple and efficient synthesis of acrylamides.

Palladium-catalysed arylation of butyl acrylate and acrylamide with aryl Iodides in water

The Heck arylation of butyl acrylate and acrylamide with aryl iodides in the presence of catalytic amounts of palladium acetate and tetra-n-butylammonium bromide in pure water using potassium carbonate as base gave the corresponding substituted (E)-butyl cinnamates and (E)-cinnamamides in good yields, respectively.

A convenient selenium-linking strategy for traceless solid-phase synthesis of diethyl 1-alkenephosphonates

Abstract Treatment of a novel polymer‐supported α‐diethoxyphosphoryl methyl selenide with LDA followed by alkylation and oxidative deselenation efficiently afforded diethyl trans‐1‐alkenephosphonates in good yields and purities.

A Simple and Efficient Method for the Preparation of Heterocyclic N-Oxide

Abstract Pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,6-dimethylpyridine, quinoline, isoquinoline and 2-chloropyridine are readily oxidized to their N-oxides with a solution of trichloroisocyanuric acid, acetic acid, sodium acetate and water in acetonitrile and methylene dichloride in 78%–90% yields.

Stereoselective synthesis of 1,3-enynylsilanes via hydromagnesiation reaction of alkynylsilanes

Hydromagnesiation of alkynylsilanes gives (Z)-α-silylvinyl Grignard reagents, which are cross-coupled with alkynyl iodides in the presence of tetrakis(triphenylphosphine)palladium(0) catalyst to afford stereoselectively 1,3-enynylsilanes in good yields.

Heck arylation of conjugated alkenes catalysed by a silica-supported poly-γ-methylselenopropylsiloxane palladium(0) complex, the first polymeric organoselenium palladium complex

A silica-supported poly-γ-methylselenopropylsiloxane palladium(0) complex was prepared from poly-γ-chloro-propylsiloxane by treatment with sodium methyl-selenolate, followed by reaction with palladium chloride and then reduction with hydrazine hydrate. The first polymeric organoselenium palladium complex is a highly active and stereoselective catalyst for the arylation of conjugated alkenes.