26423-89-2

Upstream product

• 108-86-1 bromobenzene 
• 623-43-8 methyl crotonate 
• 1067-74-9 Methyl diethylphosphonoacetate 
• 98-86-2 acetophenone 
• 917-54-4 methyllithium 
• 4891-38-7 phenylpropynoic acid methyl ester 
• 917-64-6 methyl magnesium iodide 
• 103-26-4 Methyl cinnamate 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 
• 591-50-4 iodobenzene 
• 623-43-8 crotonic acid methyl ester 
• 116-54-1 dichloroacetic acid methyl ester 
• 98-80-6 phenylboronic acid 

Downstream Products

• 84009-52-9 2,3-Dimethyl-5-oxo-2,3-diphenyl-cyclopentanecarboxylic acid methyl ester 
• 1441-20-9 (R)-(-)-3-phenylbutyric acid methyl ester 
• 54976-39-5 (Z)-(4-bromobut-2-en-2-yl)benzene 
• 54976-37-3 (Z)-3-phenyl-2-buten-1-ol 

Relevant academic research and scientific papers

Gallium-assisted transfer hydrogenation of alkenes

We report a rare case of alkene transfer hydrogenation using a main-group compound instead of a transition-metal complex as catalyst. We disclosed that 1, 4-cyclo-hexadiene can be used as H2 surrogate towards olefin reduction in the presence of [IPrGaCl2][SbF6]. Hydrogenative cycli-zations have also been carried out because this cationic gallium complex is also a potent hydroarylation catalyst.

Pd-arylurea complexes for the Heck arylation of crotonic and cinnamic substrates

A catalyst consisting of the 1:2 complex of Pd(OAc)2 (1 mol %) with N-(4-carbethoxy)-phenylurea promotes the Heck arylation of a range of crotonic and cinnamic substrates, including aldehydes, ketones, esters, and nitriles, with electron-rich - but not electron-deficient - aryl iodides.

Highly porous chitosan microspheres supported palladium catalyst for coupling reactions in organic and aqueous solutions

Porous chitosan microspheres (PCMS) were prepared from crosslinking chitosan/polyethylene glycol (PEG) interpenetrating microspheres through selective dissolution of the water-soluble PEG component for the immobilization of palladium catalyst. The resultant Pd/PCMS supported palladium has been demonstrated as a highly active and easily recyclable heterogeneous catalyst for the Ullmann-type reductive homocoupling of aromatic halides and the Heck cross-coupling of aromatic halides with acrylates. Most interestingly, the prepared Pd/PCMS heterogeneous palladium catalyst can also be employed in the environmentally-benign aqueous solution due to the highly hydrophilic hydroxyl and amino functional groups of chitosan. The large size of the microsphere structure can greatly facilitate separation and recycling of the expensive and toxic palladium catalysts from the reaction mixture and the recovered Pd/PCMS catalyst can preserve the catalytic activity and selectivity for the Heck reaction without any observable degradation over ten recycling times. The high activity and stability of the Pd/PCMS catalyst have been attributed to a combination of the high specific surface area of the porous structure as well as the strong chelation of palladium species with the abundant chitosan surface hydroxyl, amino and carbonyl functional groups.

Mild, efficient, and robust method for stereocomplementary iron-catalyzed cross-coupling using (E)- and (Z)-enol tosylates

Iron-catalyzed cross-coupling of Grignard reagents (RMgX) with (E)- and (Z)-enol tosylates proceeded smoothly to give a variety of the corresponding (E)- and (Z)-trisubstituted ,-unsaturated methyl esters (total 30 examples; 55-98% yield). The simple, mild, stereoretentive method utilized iron(III) chloride (FeCl3), iron(III) acetylacetonate [Fe(acac)3], and iron(III) tris(dibenzylmethane) [Fe(dbm). The (E)- and (Z)-enol tosylates were readily prepared by the reported stereocomplementary tosylation method from methyl -keto esters or -formyl esters. Methyl -formyl esters were obtained via a practical and robust TiCl4-Et3N-mediated -formylation of methyl esters with methyl formate.

An efficient procedure based on a MW-assisted Horner-Wadsworth-Emmons reaction for the synthesis of (Z)-3,3-trisubstituted-α,β-unsaturated esters

A microwave-assisted HWE olefination process of readily accessible aryl-alkyl ketones has been developed to provide a rapid access to (Z)-3,3-trisubstituted-α,β-unsaturated methyl esters, key building blocks for the synthesis of biologically active compou

General, robust, and stereocomplementary preparation of β-ketoester enol tosylates as cross-coupling partners utilizing TsCl-N-methylimidazole agents

(Chemical Equation Presented) We have developed a general, robust, and cost-effective method for the (E)- or (Z)-stereocomplementary enol tosylation of β-ketoesters using TsCl-N-methylimidazole (NMI)-Et3N or LiOH. TsCl coupled with NMI formed a

Palladium-catalyzed enantioselective conjugate addition of arylboronic acids

(Chemical Equation Presented) The first asymmetric palladium-catalyzed conjugate addition of arylboronic acids to α,β-unsaturated aldehydes, ketones, and esters is described. For cyclic substrates, excellent chemo-, regio-, and enantioselectivities are achieved when a Pd(O2CCF 3)2/DuPHOS catalyst is applied.

Highly active Pd(II) cyclometallated imine catalysts for the Heck reaction

The new cyclopalladated, phosphine-free imine complexes 1-3 are exceptional catalysts for the Heck arylation, leading to more than a million turnovers in some cases; the catalysts are very thermally and air stable and are recovered unchanged after the catalysis.

Zinc metal-promoted stereoselective olefination of aldehydes and ketones with gem-dichloro compounds in the presence of chlorotrimethylsilane

A combination of zinc metal and a catalytic amount of chlorotrimethylsilane has been found to promote the transformation of various aldehydes and ketones with gem-dichloro compounds, such as benzylidene dichloride (1a) and methyl dichloroacetate (1b), to the corresponding cross- coupling products, such as substituted styrene 3 and methyl acrylates 4 derivatives, under mild reaction conditions in THF. The E-isomer of the corresponding alkenes was obtained stereoselectively in good-to-excellent yields. The reaction serves as a very convenient one-pot procedure.

New reaction mode of the Horner-Wadsworth-Emmons reaction using Sn(OSO2CF3)2 and N-ethylpiperidine

Excellent Z or E selectivity is observed in the Horner-Wadsworth-Emmons reactions of methyl bis(trifluoroethyl)phosphonoacetate 2 with aryl alkyl ketones 3a-d or aldehydes 3f,g using Sn(OSO2CF3)2 in the presence of N-ethylpiperidine, which should have a different reaction mode to those using sodium hydride.