Yangjie Wu

Copper(I)-Catalyzed Sulfonylation of 8-Aminoquinoline Amides with Sulfonyl Chlorides in Air.

A simple and mild protocol for copper(I)-mediated sulfonylation of 8-aminoquinoline amides with sulfonyl chlorides was developed, affording desired products in moderate to good yields. This reaction proceeds in air and features excellent substrate tolerance, especially for aliphatic sulfonyl chlorides.

Studies on the cyclometallation of ferrocenylimines

Abstract This review describes the cyclometallation reaction, including cyclomercuration, cyclopalladation and cycloplatination of Schiff base type of ferrocenylimines as well as the transmetallation reaction of cyclometallated ferrocenylimines and the stereochemistry associated with these reactions. The applications of cyclopalladated ferrocenylimines in several fields are also demonstrated in this review. The molecular and crystal structures of the products as well as the absolute configurations of optically active products were established by X-ray diffraction, NMR techniques, IR, UV–vis, etc. The general features of these reactions, especially the regioselectivity and the reaction mechanisms, are discussed. In addition, the structure–property relationships are discussed throughout this investigation. The transmetallation of optically pure cyclometallated ferrocenylimines with other metals such as mercury, tin and tellurium was found to proceed with complete retention of stereochemistry. This discovery led to a convenient method for the synthesis of optically pure cyclometallated organic compounds that are difficult to prepare by using conventional methods. Accordingly, a number of cyclometallated ferrocenylimines have been prepared in optically pure forms, which display surprisingly high angles of rotation.

Palladium-Catalyzed Three-Component Arylcyanation of Internal Alkynes with Aryl Bromides and K4[Fe(CN)6]

The one-pot, palladium-catalyzed, three-component coupling of aryl bromides, internal alkynes, and environmentally friendly K4[Fe(CN)6] provides an efficient and direct method for the preparation of beta-arylalkenylnitriles.

Cyclopalladated ferrocenylimines: highly active catalysts for Heck reactions

A novel kind of ferrocene moiety containing palladacycle catalysts 1 and 2 was synthesized and applied to Heck arylation. High yields, turnover numbers and regioselectivity were achieved in moderate conditions. When 2.73×10−8 mol catalyst 2 was used to catalyze arylation of 0.1 mol iodobenzene with butyl acrylate, optimal results were obtained with 3.6×106 turnover number and 99% yield.

Polymer (fiber)-supported palladium catalyst containing imidazolinyl rings and its application to the Heck reaction

A polymer (fiber)-supported palladium catalyst was synthesized simply from commercially available polyacrylonitrile(PAN) fiber. Its high activity and selectivity for Heck reactions were measured; its activity remained unchanged after being recycled 20 times.

Synthesis, Characterization, and Crystal Structures of Three cis/trans Pyridine–Cyclopalladated Ferrocenylimine Complexes, and Their Catalysis in Suzuki Reactions

Three new pyridine–cyclopalladated ferrocenylimine complexes 2a–c have been easily prepared and characterized by elemental analysis, ESI-MS, 1H NMR, and IR spectra. Their detailed structures are determined by single-crystal X-ray analysis. Palladacycle 2a is found to be a cis complex in the solid state, while 2b and 2c are trans complexes. These complexes were found to be efficient for the Suzuki reaction of aryl bromides with phenylboronic acid. Typically, using 0.2 mol% of 2c in the presence of 1.5 equivalents of K2CO3 as base in toluene at 100°C provided the coupled products in good to excellent yields.

A highly pure red luminescent europium(III) complex with a Schiff base zinc(II) complex as a neutral ligand

A highly pure red luminescent heterobimetallic complex [EuZnL(tta)2(μ-tfa)] (L = N,N′-bis(salicylidene)-2,3-propanediamine, tta = 2-thenoyltrifluoroacetonate, tfa = trifluoroacetate) was synthesized. The EL device with this complex exhibits an inspiring current efficiency of 3.7 cd A−1 at a brightness of 300 cd m−2 and gives a maximum Eu(III)-based pure red emitting luminance of 1982.5 cd m−2 at 13.8 V.

Tricyclohexylphosphine-cyclopalladated ferrocenylimine complexes: synthesis, crystal structures and application in Suzuki and Heck reactions

A series of novel tricyclohexylphosphine (PCy(3))-cyclopalladated ferrocenylimine complexes 2c-2g have been easily synthesized. These new palladacycles are thermally stable and are not sensitive to air and moisture. Their detailed structures have been determined by single-crystal X-ray analysis and six different types of intermolecular hydrogen bonds are found to be existed in the crystals of these complexes. The use of 2c-2g as catalysts for Suzuki and Heck reactions was examined. They were found to be very efficient for the Suzuki reaction of aryl chlorides with phenylboronic acid. Typically, using 0.1 mol% of catalyst in the presence of 1.5 equivalent of Cs(2)CO(3) as base in dioxane at 100 degrees C provided coupled products in excellent yields. These complexes also displayed good activity in the Heck reaction of a range of aryl bromides with acrylic acid ethyl ester although they were not particularly useful for the activation of aryl chlorides.

Synthesis of novel chiral tellurium complexes by redox reaction of planar chiral cyclomercurated ferrocenylimines with tellurium powder and X-ray crystal structure of [TeCl{C5H5FeC5H3C(CH3)N-C6H4-4-CH3}]

Abstract The redox reaction of planar chiral cyclomercurated ferrocenylimines (R)-(+)-[HgCl{C5H5FeC5H3C(CH3)NAr}] (Ar=substituted phenyl) with tellurium powder was carried out in refluxing toluene to give optically active cyclotellurated ferrocenylimines (R)-(+)-[TeCl{C5H5FeC5H3C(CH3)NAr}], which were characterized by elemental analysis, IR and 1H NMR spectra. The redox reaction proceeded with retention of the planar chirality in the ferrocene moiety, which was confirmed by CD spectra. The crystal structure of [TeCl{C5H5FeC5H3C(CH3)N-C6H4-4-CH3}] showed that the TeN distance of 2.28 A is shorter than the sum of the van der Waals radii of Te and N (3.70 A), indicating the presence of N→Te intramolecular coordination.

Studies on the synthesis and structural characterization of cyclomercurated ferrocenylimines containing heterocyclic ring

Abstract The cyclomercurated ferrocenylimines containing heterocyclic ring can be prepared by the cyclomercuration of acylferrocene, followed by the condensation of the resulting product with the appropriate heterocyclic amine. This procedure provides an efficient method for the synthesis of cyclomerucurated ferrocenylimines containing heterocyclic ring which is difficultly synthesized by the traditional method, i.e. imination and then cyclomercuration. A series of these compounds were synthesized by this new method and characterized. The X-ray crystal structure of [HgCl(η 5 -C 5 H 3 C(CH 3 )N-2-C 5 H 3 N-6-CH 3 ) Fe(η 5 -C 5 H 5 )] ( 3d ) has been determined and the reaction mechanism was proposed.