125315-69-7

Upstream product

• 618-34-8 1-chlorostyrene 
• 100-52-7 benzaldehyde 
• 591-50-4 iodobenzene 
• 463-49-0 1,2-propanediene 
• 3360-52-9 3-chloro-2-phenylprop-1-ene 
• 7534-40-9 2-phenylallyl acetate 
• 536-74-3 phenylacetylene 
• 3420-52-8 1,4-Diphenylprop-3-en-1-one 
• 98-81-7 1-bromovinylbenzene 
• 98-86-2 acetophenone 
• 98-83-9 isopropenylbenzene 
• 51246-20-9 1-phenyl-1-iodoethylene 
• 869307-95-9 2-[dimethyl-(2-phenyl-allyl)-silanyl]-pyridine 
• 831215-57-7 β-phenylallyltrichlorosilane 

Downstream Products

• 62326-47-0 1,3-diphenyl-3-buten-1-one 
• 1106719-21-4 (S)-5-methyl-3,5-diphenyl-4,5-dihydroisoxazole 
• 1221447-17-1 (E)-1,3-diphenylbut-3-en-1-one oxime 
• 54435-79-9 (E)-1,3-diphenyl-3-methyl-2-propen-1-one 
• 20698-95-7 (3S)-1,3-diphenylbutan-1-one 
• 1533-20-6 (3R)-1,3-diphenylbutan-1-one 

Relevant academic research and scientific papers

Palladium-indium mediated Barbier-type allylation of aldehydes with allenes

A new allylation reaction of carbonyl compounds using allenes is described; homoallylic alcohols were obtained in moderate to good yields from aryl iodides, allenes and carbonyl compounds and an excellent diastereoselection was exhibited when 2-hydroxycyclohexanone was employed.

Platinum(0)-catalyzed diboration of allenes with bis(pinacolato)diboron

Addition of bis(pinacolato)diboron [(Me4C2O2)B-B(O2C2Me4)] to various allenes was carded out in excellent yields in the presence of Pt(PPh3)4 at 80 °C or Pt(dba)2/(c-Hex)3P at 50 °C. The addition to internal double bond was predominant for monosubstituted allenes, whereas the terminal diboration products were regioselectively obtained when a sterically bulky phosphine ligand of (c-Hex)3P and 1,1-disubstituted allenes were used.

Three-component bimetallic (Pd/In) mediated cascade allylation of C=X functionality Part 1. Scope and Class 1 examples with aldehydes and ketones

A new general three-component Pd/In bimetallic cascade reaction with four synthetic variants involving aryl iodides, allenes and C=X compounds affording homoallylic alcohols/amines as products is described and exemplified for Class 1 processes (intermolecular Pd-intermolecular In steps). Remarkable increases in yield and reaction rates were observed in the presence of amine additives. Excellent diastereoselection is exhibited when 2-hydroxycyclohexanone is employed, and semi-empirical and ab initio calculations are used to rationalise the observed syn: anti diastereoselectivity.

Additive effects in palladium-indium mediated Barbier type allylations

The effect of adding 1 equiv. of an amine or 0.2 equiv. of CuI to a Pd/In bimetallic cascade reaction is described. In the class 1 cascade reaction of aldehydes, aryl iodides and allene, generating homoallylic alcohols, the reaction time is reduced from 16 to 2 h and is accompanied by an impressive increase in yield.

Visible Light-Promoted Recyclable Carbon Nitride-Catalyzed Dioxygenation of β,γ-Unsaturated Oximes

A visible-light-induced dioxygenation of β,γ-unsaturated oximes for the synthesis of diverse useful isoxazolines bearing a hydroxyl moiety was developed by employing graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst under an air atmosphere. Noted that, the eminent advantages of this metal-free protocol include step economy, easy operation, a recyclable photocatalyst, external reductant-/oxidant-free and mild reaction conditions. Additionally, mechanistic studies indicated hydroxyl radical was generated under the photocatalysis of g-C3N4.

Copper-Catalyzed Aerobic Cyclization of β,γ-Unsaturated Hydrazones with Concomitant CC Bond Cleavage

A Cu-catalyzed aerobic oxidative cyclization of β,γ-unsaturated hydrazones for the preparation of pyrazole derivatives has been developed. The hydrazonyl radical promoted the cyclization, along with a concomitant CC bond cleavage of β,γ-unsaturated hydrazones. This process has been verified via several control experiments, including a radical-trapping study, an 18O-labeling method, and the identification of the possible byproducts. The advantages of this reaction include operational simplicity, a broad reaction scope, and a mild selective reaction process.

A Copper Catalyst with a Cinchona-Alkaloid-Based Sulfonamide Ligand for Asymmetric Radical Oxytrifluoromethylation of Alkenyl Oximes

A copper-catalyzed asymmetric radical oxytrifluoromethylation of alkenyl oxime and Togni's reagent has been successfully developed, thereby providing straightforward access to CF3-containing isoxazolines bearing α-tertiary stereocenters with excellent yield and enantioselectivity. The key to success is the rational design of cinchona-alkaloid-based sulfonamides as neutral/anionic hybrid ligands to effectively control the stereochemistry in copper-catalyzed reactions involving free alkyl radical species. The utility of this method is illustrated by efficient transformation of the products into useful chiral CF3-containing 1,3-aminoalcohols.

Rhodium-Catalyzed Enantioconvergent Isomerization of Homoallylic and Bishomoallylic Secondary Alcohols

We present herein an unprecedented enantioselective isomerization of homoallylic and bishomoallylic secondary alcohols, catalyzed by a commercially available rhodium-complex and a base. This catalytic redox-neutral process provides an effective access to chiral ketones in high efficiency and enantioselectivity, without the use of any stoichiometric reagent or generation of any waste. For the reaction of homoallylic alcohols, this system achieved not only a stereoconvergent access to chiral ketones bearing a β-stereocenter (up to 95%, 86% ee) but also a concomitant oxidative kinetic resolution of the alcohol substrates (S > 20). In the case of bishomoallylic alcohols, an intriguing ligand-induced divergent reactivity was observed. A terminal-to-internal alkene isomerization promoted by Rh/L7 followed by redox isomerization using Rh/BINAP system produced chiral ketones bearing a γ-stereocenter with high yield and enantioselectivity. Mechanistic studies provided strong support for the redox-isomerization pathway with chain walking of the key alkyl-Rh intermediate.

Copper-catalyzed radical oxytrifluoromethylation of alkenyl oximes at ambient temperature

A mild and efficient copper-catalyzed radical oxytrifluoromethylation reaction of alkenyl oximes was successfully developed. The method provides a straightforward access to a wide range of CF3-containing isoxazolines in good to excellent yields.

Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates

Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates has been developed for efficient synthesis of various allyltrimethylsilanes. The cross-coupling reaction was conducted at room temperature with low catalyst loading of either Pd(PPh3)4 or Pd(PPh3)2Cl2, and exhibited high efficiency and a broad substrate scope. In combination with the cross-coupling by the Lewis-acid catalyzed Hosomi-Sakurai reaction, a novel three-component one-pot cascade reaction was then accomplished to deliver homoallylic alcohols and ethers with high regioselectivity and diastereoselectivity. The three-component reaction defined the yttrium complex as a novel one-carbon synthon, which could either trigger bifunctionalization of alkenes or link two electrophiles and would find applications in organic synthesis.