113592-34-0

Upstream product

• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 6628-68-8 ethyl 2-(ethoxycarbonyl)-4-phenylbutanoate 
• 3709-38-4 2,2-dimethyl-5-phenethyl-[1,3]dioxane-4,6-dione 
• 128038-39-1 2-methylene-4-phenylbutanoic acid 
• 30982-08-2 methyl 2-(1-acetoxymethyl)acrylate 
• 100-39-0 benzyl bromide 
• 620-05-3 iodomethylbenzene 
• 4224-69-5 methyl 2-(bromomethyl)propenoate 
• 1589-82-8 phenylmagnesium bromide 
• 16520-62-0 4-Phenyl-1-butyne 
• 201230-82-2 carbon monoxide 
• 38131-57-6 2-benzenesulfonylmethacrylic acid methyl ester 
• 66310-10-9 N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate 

Downstream Products

• 113592-35-1 2-[(1-Benzyloxycarbonylamino-ethyl)-methoxy-phosphinoylmethyl]-4-phenyl-butyric acid methyl ester 
• 113592-33-9 2-[(1-Amino-ethyl)-hydroxy-phosphinoylmethyl]-4-phenyl-butyric acid 
• 102617-51-6 methyl 2-(cyclohexylmethyl)acrylate 
• 102617-50-5 3-Cyclohexyl-2-(cyclohexylmethyl)propionsaeure-methylester 
• 124481-69-2 2-Cyclohexylmethyl-4-phenyl-butyric acid methyl ester 

Relevant academic research and scientific papers

Room-temperature Pd-catalyzed methoxycarbonylation of terminal alkynes with high branched selectivity enabled by bisphosphine-picolinamide ligand

We report the room-temperature Pd-catalyzed methoxy-carbonylation with high branched selectivity using a new class of bisphosphine-picolinamide ligands. Systematic optimization of ligand structures and reaction conditions revealed the significance of both

Catalyst-Free Deaminative Functionalizations of Primary Amines by Photoinduced Single-Electron Transfer

The use of pyridinium-activated primary amines as photoactive functional groups for deaminative generation of alkyl radicals under catalyst-free conditions is described. By taking advantage of the visible light absorptivity of electron donor–acceptor complexes between Katritzky pyridinium salts and either Hantzsch ester or Et3N, photoinduced single-electron transfer could be initiated in the absence of a photocatalyst. This general reactivity platform has been applied to deaminative alkylation (Giese), allylation, vinylation, alkynylation, thioetherification, and hydrodeamination reactions. The mild conditions are amenable to a diverse range of primary and secondary alkyl pyridiniums and demonstrate broad functional group tolerance.

Metal-free desilylative C-C bond formation by visible-light photoredox catalysis

A newly developed methodology for the use of organosilanes as radical precursors under metal-free and visible-light conditions is presented. The strong oxidant character of the 9-mesityl-10-methylacridinium salt in its excited state enables the transforma

Palladium-Catalyzed Electrochemical Allylic Alkylation between Alkyl and Allylic Halides in Aqueous Solution

A new route for the direct cross-coupling of alkyl and allylic halides using electrochemical technique has been developed in aqueous media under air. Catalyzed by Pd(OAc)2, the Zn-mediated allylic alkylations proceed smoothly between a full range of alkyl halides (primary, secondary, and tertiary) and substituted allylic halides. Protection-deprotection of acidic hydrogen in the substrates is avoided.

Cobalt-Catalyzed Cross-Coupling of Grignards with Allylic and Vinylic Bromides: Use of Sarcosine as a Natural Ligand

Sarcosine was discovered to be an excellent ligand for cobalt-catalyzed carbon-carbon cross-coupling of Grignard reagents with allylic and vinylic bromides. The Co(II)/sarcosine catalytic system is shown to perform efficiently when phenyl and benzyl Grignards are coupled with alkenyl bromides. Notably, previously unachievable Co-catalyzed coupling of allylic bromides with Grignards to linearly coupled α-products was also realized with Co(II)/sarcosine catalyst. This method was used for efficient preparation of the key intermediate in an alternative synthesis of the antihyperglycemic drug sitagliptin.

D-Glucosamine in iron-catalysed cross-coupling reactions of Grignards with allylic and vinylic bromides: Application to the synthesis of a key sitagliptin precursor

A sustainable D-glucosamine ligand is successfully introduced into iron-catalysed C-C cross-coupling reactions for the first time. The Fe(acac)2/D-glucosamine·HCl/Et3N catalytic system was effective at 5 mol% loading in coupling reactions of Grignard reagents with organic bromides. Moderate to high efficiency was achieved with preserved stereochemistry when allyl (Csp3) or alkenyl (Csp2) bromides were coupled with phenylmagnesium (Csp2) or benzylmagnesium (Csp3) bromides. The catalytic system developed was also successfully applied for the novel and economic preparation of a Michael-acceptor-like starting material used in an alternative synthesis of the drug sitagliptin, a known blockbuster for the treatment of type II diabetes mellitus.

Radical additions to allyl bromides. A synthetically useful, 'Tin-Free' method for carbon-carbon bond formation

The scope and limitations of a novel free radical chain process involving the addition of benzyl radicals to substituted allyl bromides were examined and extended to explore the effect of α-substitution on the allyl bromide (R′), and the use of pyrrolidine amides and oxazolidinone as activating substituents (Z) as the first steps toward the development of a stereoselective, radical-based C-C bond-forming reaction which is environmentally benign.

Titanocene(III) chloride mediated radical-induced addition to Baylis-Hillman adducts: Synthesis of (E)- and (Z)-trisubstituted alkenes and α-methylene/arylidene δ-lactones

(Chemical Equation Presented) Baylis-Hillman adduct underwent smooth radical-induced condensation with activated bromo compounds and epoxides using titanocene(III) chloride (Cp2TiCl) as the radical generator. The reactions of activated bromo co

Radical-mediated hydroxyalkylation of α,β-unsaturated esters

The radical-mediated hydroxyalkylation of α,β-unsaturated esters with alkyl iodides, trialkylborane, water and KF in THF gave the corresponding α-hydroxy esters. The synthetic advantage of the method was demonstrated by a short-step total synthesis of (±)

Facile synthesis of α-substituted acrylate esters

Treatment of 5-monosubstituted Meldrum's acids with dimethylmethyleneimmonium iodide (Eschenmoser's iodide salt) in methanol gives α-substituted acrylate methyl esters in good yields. Easy access to 5-monosubstituted Meldrum's acids allowed us to synthesize a wide variety of α-substituted acrylate methyl esters. The reaction conditions are mild and tolerate many functional groups commonly used in organic synthesis; thus, this new method has potential as an alternative to conventional preparative methods for α-substituted acrylate esters.