5320-30-9

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 50488-52-3 diphenyl (cyanomethyl)phosphonate 
• 15898-47-2 (cyanomethyl)triphenylphosphonium bromide 
• 433231-64-2 C₂₀H₁₀F₁₂NO₂P 
• 104-54-1 3-Phenylpropenol 
• 16640-68-9 cyanomethylene triphenylphosphorane 
• 4336-70-3 (cyanomethyl)triphenylphosphonium chloride 
• 1823-14-9 5-phenyl-1-pentyne 

Downstream Products

• 7726-45-6 5-phenylvaleronitrile 

Relevant academic research and scientific papers

Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles via aerobic oxidative N-incorporation

A novel direct transformation of aliphatic terminal alkynes to alkenyl nitriles through the incorporation of a nitrogen atom into the simple hydrocarbons has been reported. The usage of inexpensive copper catalyst, O2 as the sole oxidant, broad substrate scope as well as feasibility for "late-stage modification" make this protocol very promising. Mechanistic studies including DFT calculation demonstrate a novel 1,2-hydride shift process for this novel nitrogenation reaction.

Wittig Olefination Using Phosphonium Tetraphenylborate in the Absence of Additional Base

The thermal decomposition of (substituted methyl)triphenylphosphonium tetraphenylborates, which can also be generated in situ from the corresponding phosphonium halide and NaBPh4, with an aldehyde affords olefins in 22-100% yields. This Wittig olefination does not need use additional base to form phosphorus ylide, and is highly tolerant of benzoic acid.

Borrowing hydrogen: Indirect "Wittig" olefination for the formation of C-C bonds from alcohols

The successful development of an indirect three-step domino sequence for the formation of C-C bonds from alcohol substrates is described. An iridium-catalysed dehydrogenation of alcohol 1 affords the intermediate aldehyde 2. The desired C-C bond can then be formed by a facile Wittig olefination, yielding the intermediate alkene 3. In the final step the alkene is hydrogenated to afford the indirect Wittig product, the alkane 4. The key to this process is the concept of borrowing hydrogen; hydrogen removed in the initial dehydrogenation step is simply borrowed by the iridium catalyst. Functioning as a hydrogen reservoir, the catalyst facilitates C-C bond formation before subsequently returning the borrowed hydrogen in the final step. Herein we present full details of our examination into both the substrate and reaction scope and the limitations of the catalytic cycle. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Highly Z-selective synthesis of disubstituted α, β-unsaturated cyanides and amides using 10-P-5 wittig type reagents

Phosphoranes (10-P-5) bearing cyanomethyl, acetamide, and N, N-dimethylacetamide groups were examined for Wittig type reactions. All three reacted to give the corresponding olefins. The reaction of the cyanomethyl reagent with aldehydes gave α, β-unsatura

The reaction of triphenylphosphonium or triphenylarsonium salts with aldehyde: Effect of the counteranion on their reactivity

Some acetonyltriphenylphosphonium, methoxycarbonylmethyltriphenylphosphonium salts and their triphenylarsonium analogues could undergo Wittig reaction with aldehyde in good yields. Their reactivity was counteranion-dependent and was arranged in the following order: p-TsO-, Br-3CO2/-2CO2/-2/-, HCO2/-, MeCO2/-. The proton-coupled 13C NMR splitting patterns of the α-methylene groups provided a valuable information to predict their reactivity with aldehyde. Only those onium salts without C-H coupling could undergo Wittig reaction. (C) 2000 Elsevier Science Ltd.

An efficient and practical synthesis of diphenyl cyanomethylenephosphonate: Applications to the stereoselective synthesis of cis-α,β-unsaturated nitriles

Diphenyl cyanomethylenephosphonate (PhO)2POCH2CN was prepared as a stable crystalline solid in high yield in a single step from acetonitrile, LDA, and (PhO)2P(O)CI. The potassium ylide generated from this compound afforded α,β-unsaturated nitriles upon reacting with aldehydes, with a stereoselectivity of 64-100% favoring the cis-isomer.