29638-71-9

Usage

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 2025, 1991 DOI: 10.1016/S0040-4039(00)78898-8

InChI:InChI=1/C14H16O2/c1-11(15)14(12(2)16)10-6-9-13-7-4-3-5-8-13/h3-9,14H,10H2,1-2H3/b9-6+

Upstream product

• 300-57-2 allylbenzene 
• 123-54-6 acetylacetone 
• 104-54-1 3-Phenylpropenol 
• 2687-12-9 cinnamyl chloride 
• 32121-04-3 N-cinnamyl-4-methylbenzenesulfonamide 
• 99179-38-1 3-phenyl-1-propenol 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 13858-67-8 3-cinnamylidene-pentane-2,4-dione 
• 516-09-6 4-hydroxy-3-methyl-5H-furan-2-one 
• 21040-45-9 Cinnamyl acetate 
• 30182-67-3 1,3-Cyclohexanedione 
• 106625-69-8 ethyl (E)-3-phenyl-2-propenyl carbonate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 4392-24-9 Cinnamyl bromide 

Downstream Products

• 1432739-10-0 1-(5-benzyl-1-(4-methoxyphenyl)-2-methyl-1H-pyrrol-3-yl)ethanone 

Relevant academic research and scientific papers

Monoallylation and benzylation of dicarbonyl compounds with alcohols catalysed by a cationic cobalt(iii) compound

Monoallylation and monoalkylation of diketones and β-keto esters with allylic and benzylic alcohols catalysed by [Cp*Co(CH3CN)3][SbF6]2(I) are reported. The method does not require any additive and affords regioselective products. The mechanistic investigations were done byin situ1H NMR spectroscopy as well as control experiments. It has been shown that reactions proceedviaη3-allyl complex formation or ally ether intermediate. The alkylation takes placeviaonly ether intermediate. The resulting allylated and alkylated products have been used for the synthesis of eleven new trisubstituted pyrazoles and one pyrazolone.

Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- And α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol

The B(C6F5)3-catalyzed chemoselective hydrosilylation of α,β- and α,β,γ,δ-unsaturated ketones into the corresponding non-symmetric ketones in mild reaction conditions is developed. Nearly 55 substrates including those bearing reducible functional groups such as alkynyl, alkenyl, cyano, and aromatic heterocycles are chemoselectively hydrosilylated in good to excellent yields. Isotope-labeling studies revealed that hexafluoro-2-propanol also served as a hydrogen source in the process.

Iridium/ N-Heterocyclic Carbene Complex-Catalyzed Intermolecular Allylic Alkylation Reaction

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Regio- and Enantioselective Rhodium-Catalyzed Allylic Alkylation of Racemic Allylic Alcohols with 1,3-Diketones

Highly regio- and enantioselective rhodium-catalyzed allylic alkylation of 1,3-diketones with racemic secondary allylic alcohols is reported. In the presence of a Rh-catalyst derived from the Carreira (P, olefin)-ligand and TFA as an additive, chiral branched α-allylated 1,3-diketones could be obtained in good to excellent yields, with excellent regio- and enantioselectivity (b/l > 19/1, 86-98% ee). The direct utilization of allyl alcohols as electrophiles represents an improvement from the viewpoint of an atom economy. Both aryl- and aliphatic-substituted allyl alcohols are suitable substrates with excellent reaction outcomes. This reaction features mild conditions, broad substrate scope, and readily available substrates.

Palladium-Catalyzed Oxidative Cycloisomerization of 2-Cinnamyl-1,3-Dicarbonyls: Synthesis of Functionalized 2-Benzyl Furans

A new palladium-catalyzed intramolecular oxidative cycloisomerization of readily available starting materials, 2-cinnamyl-1,3-dicarbonyls, has been demonstrated for the creation of structurally diverse 2-benzyl furans. The cycloisomerization occurs by a regioselective 5-exo-trig pathway. The reaction shows a broad substrate scope with good to excellent yields. Furthermore, a one-pot procedure has been executed by using readily available cinnamyl alcohols and 1,3-diketones. Cinnamyl verit: Palladium-catalyzed intramolecular oxidative cycloisomerization of readily available 2-cinnamyl-1,3-dicarbonyls affords structurally diverse 2-benzyl furans. The cycloisomerization occurs by a regioselective 5-exo-trig pathway, with a broad substrate scope in good to excellent yields. Furthermore, a one-pot procedure is executed by using readily available cinnamyl alcohols and 1,3-diketones

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A dual platinum- and pyrrolidine-catalyzed direct allylic alkylation of allylic alcohols with various active methylene compounds to produce products with high monoallylation selectivity was developed. The use of pyrrolidine and acetic acid was essential, not only for preventing undesirable side reactions, but also for obtaining high monoallylation selectivity. Two cats are better than one: The combined use of platinum and pyrrolidine catalysts enabled the direct alkylation of allylic alcohols with reactive methylene compounds. Pyrrolidine was essential for obtaining high selectivity of the monoallylation products, which were produced without the use of excess nucleophiles. cod=1,5- cyclooctadiene, EWG=electron-withdrawing group.

Multimetallic Ir-Sn3-catalyzed substitution reaction of π-activated alcohols with carbon and heteroatom nucleophiles

An atom economic and catalytic substitution reaction of π-activated alcohols by a multimetallic IreSn3 complex has been demonstrated. The multimetallic IreSn3 complex can be easily synthesized from the reaction between [Cp*IrCl2]2 and SnCl2. In presence of as little as 1 mol % of the catalyst three different types of π-activated alcohols, namely benzyl, allyl, and propargyl alcohols, have been successfully transformed into alkylated products using carbon (arenes, heteroarenes, allyltrimethylsilane, and 1,3-dicarbonyls), nitrogen (sulfonamides), oxygen (alcohols), and sulfur (thiols) nucleophiles in very high yields. An electrophilic mechanism is proposed from the Hammett correlation study.

Efficient synthesis of highly substituted pyrroles through a Pd(OCOCF 3)2-catalyzed cascade reaction of 2-alkenal-1,3-dicarbonyl compounds with primary amines

We describe an unprecedented Pd(OCOCF3)2-catalyzed cascade process for the synthesis of highly functionalized 1,2,3,5- tetrasubstituted pyrroles with high efficiency. Unlike documented methods relying on preformed enamines and active halogenated terminal alkenes, the process employs simple 2-alkenal-dicarbonyls and primary amines in 'one-pot'. The Royal Society of Chemistry 2013.

Different products in the reaction of the alcohols with cyclic and acyclic 1,3-dicarbonyl compounds: K5CoW12O40 as an electron transfer nano catalyst

K5CoW12O40 was used as a highly effective catalyst for the benzylation of 1,3-dicarbonyl compounds. β-Keto enol ethers were obtained when cyclic 1,3-dicarbonyl compounds used in this conditions instead of linear ones. The present methodology offers a practical, simple, mild, environmentally friendly, and time-saving method for etherification. Very low loading of catalyst, ease of workup, ease of handling, and reusability of catalyst are other advantages of this catalyst.