106925-11-5

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 104-55-2 3-phenyl-propenal 
• 535-15-9 ethyl 1,1-dichloroacetate 
• 105-36-2 ethyl bromoacetate 
• 603-35-0 triphenylphosphine 
• 104-54-1 3-Phenylpropenol 
• 17577-28-5 (ethoxycarbonylmethyl)triphenylphosphonium chloride 
• 57194-69-1 cinnamaldehyde 
• 188945-44-0 ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 4610-69-9 (Z)-ethyl cinnamate 
• 31930-36-6 ethyl (Z)-3-iodopropenoate 
• 4363-35-3 Dihydroxy-styryl-boran 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 1379820-27-5 C₆H₅CHCHCH(BO₂C₂(CH₃)4)CH₂COOC₂H₅ 
• 38446-98-9 (2E,4Z)-5-phenylpenta-2,4-dienoic acid 

Relevant academic research and scientific papers

The first sequential reaction promoted by manganese: Complete stereoselective synthesis of (E)-α,β-unsaturated esters from 2,2-dichloroesters and aldehydes

(Chemical Equation Presented) α,β-Unsaturated esters were obtained with complete control of stereoselectivity utilizing a sequential reaction of dichloroesters with a variety of aldehydes, promoted by active manganese. This methodology is generally applicable, and the C-C double bond can be di- or trisubstituted. A mechanism based on a successive aldol-type reaction/β-elimination is proposed to explain these results.

Essential structural features of (2Z,4E)-5-phenylpenta-2,4-dienoic acid for inhibition of root gravitropism

Previously, we found (2Z,4E)-5-phenylpenta-2,4-dienoic acid (ku-76) to be a selective inhibitor of root gravitropic bending of lettuce radicles at 5 μM, with no concomitant growth inhibition. Here, we describe a structure-activity relationship study of ku

One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts

A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O 2 in air as oxidant. The solvent mixture of acetonitrile and formamide (1:1) is optimized to ensure the oxidation of alcohols, deprotonation of phosphonium salt, and Wittig reaction occur efficiently in one pot. A broad range of substrates has been explored for this process, including three electron-withdrawing group (CO 2 Et, COPh, CN) functionalized phosphonium salts. They reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields.

Tandem oxidation–Wittig reaction using nanocrystalline barium manganate (BaMnO4); an improved one-pot protocol

A one-pot, tandem oxidation–Wittig procedure has been developed in which the reacting components are generated in situ from alcohols, triphenyl phosphine, and ethyl bromoacetate using barium manganate as a mild oxidizing agent without the addition of an external base.

Polyethyleneimine-Supported Triphenylphosphine and Its Use as a Highly Loaded Bifunctional Polymeric Reagent in Chromatography-Free One-Pot Wittig Reactions

A polyethyleneimine-supported triphenylphosphine reagent has been synthesized and used as a highly loaded bifunctional homogeneous reagent in a range of one-pot Wittig reactions that afforded high yields of the desired products after simple purification procedures. The approach also served efficiently in tandem reaction sequences involving a one-pot Wittig reaction followed by conjugate reduction of the newly formed alkene product in situ. In these transformations, the phosphine oxide groups generated in the Wittig reaction served as the catalyst for activating trichlorosilane in the subsequent reduction reaction.

Diastereoselective liquid assisted grinding: 'Cracking' functional resins to advance chromatography-free synthesis

As regulations that restrict the use of organic solvents become more stringent, ball milling remains an attractive substitute for traditional organic synthesis. However, the mechanochemistry community does not have a purification pathway to complement the solvent-free, ball milling process. Functional resins have proven to be powerful synthetic tools that simplify purification, but traditional handling of these resins restricts their utility, as hazardous organic solvents are needed to swell the resin. Ball milling the functional resin exposes the functional groups as a function of surface area. This report details the use of ball milling and functional resins to perform an environmentally attractive version of the Wittig reaction.

Ligand effects on the stereochemical outcome of suzuki-miyaura couplings

The ligands associated with various Pd catalysts play a crucial role in determining the stereochemistry of cross-couplings between boronic acids and Z-alkenyl halides. A ligand on palladium has been found that leads to the desired products under mild conditions and in high yields that, in most cases, retain their Z-olefin geometry.

A two-step ball milling method synthesizes and purifies α,β-unsaturated esters

Over the last decade, solvent-free methods have been gaining interest as replacements for traditional organic chemistry techniques. While solvent-free methods are well known for many processes, a simple, solvent-free purification procedure that supplements them does not exist. We report the solvent-free synthesis of α,β-unsaturated esters using a solvent-free Horner-Wadsworth-Emmons (HWE) reaction using high-speed ball milling (HSBM). We were able to perform the HWE reaction on a variety of aldehydes, and isolate their respective a,b-unsaturated esters in high yields, purities, and diastereoselectivities. The Royal Society of Chemistry.

One-pot Wittig reaction for the synthesis of α,β-unsaturated esters using highly basic magnesium/lanthanum mixed oxide

Highly basic Mg/La mixed oxide (Mg/La MO) is an effective heterogeneous base, at room temperature for the one-pot Wittig reaction involving aldehyde, α-halo esters and triphenylphosphine to afford α,β-unsaturated esters in good yields with high E-stereoselectivity. Mg/La mixed oxide was recovered quantitatively by simple filtration and reused. The basic properties of Mg/La mixed oxide have been compared to those of nanocrystalline magnesium oxide using the microcalorimetric adsorption of CO2, and the reactivity for Wittig reactions. Mg/La mixed oxide is a stronger base than magnesium oxide (MgO) but shows a much smaller number of sites. Hammett correlations have been determined for both bases and show that the reaction is base mediated, with values of ρ = 1.7 for Mg/La mixed oxide, and 1.1 for nanocrystalline magnesium oxide, and a compensation effect can then be observed.

HMPT/zinc mediated one-pot convenient synthesis of β-substituted acrylates

A new one pot convenient synthesis of β-substituted acrylates involving the reaction of aldehydes with ethyl bromoacetate via concomitant Reformatsky and dehydration reactions prompted by HMPT and zinc has been described.