81676-11-1

Upstream product

• 1530-32-1 ethyltriphenylphosphonium bromide 
• 122-00-9 para-methylacetophenone 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 74-85-1 ethene 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 4518-65-4 (1-methoxyprop-1-en-1-yl)benzene 
• 5398-04-9 2-(4-methoxyphenyl)-2-butanol 

Downstream Products

• 114841-69-9 3-p-tolylselenophene 
• 1595-16-0 1-sec-butyl-4-methylbenzene 
• 81676-07-5 4,5-Dimethyl-5-p-tolyl-dihydro-furan-2-one 
• 119840-43-6 1-(2-Bromo-1-methyl-1-prop-2-ynyloxy-propyl)-4-methyl-benzene 
• 122-00-9 para-methylacetophenone 
• 109568-37-8 1-(3-p-tolyl-selenophen-2-yl)-ethanone-(2,4-dinitro-phenylhydrazone) 
• 108990-79-0 1-(3-p-tolyl-selenophen-2-yl)-ethanone 
• 380379-44-2 5-oxalaurene/5-oxaepilaurene 
• 119840-42-5 5-oxaisolaurene 

Relevant academic research and scientific papers

Palladium-Catalyzed Markovnikov Hydroaminocarbonylation of 1,1-Disubstituted and 1,1,2-Trisubstituted Alkenes for Formation of Amides with Quaternary Carbon

Hydroaminocarbonylation of alkenes is one of the most promising yet challenging methods for the synthesis of amides. Herein, we reported the development of a novel and effective Pd-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted or 1,1,2-trisubstituted alkenes with aniline hydrochloride salts to afford amides bearing an α quaternary carbon. The reaction makes use of readily available starting materials, tolerates a wide range of functional groups, and provides a facile and straightforward approach to a diverse array of amides bearing an α quaternary carbon. Mechanistic investigations suggested that the reaction proceeded through a palladium hydride pathway. The hydropalladation and CO insertion are reversible, and the aminolysis is probably the rate-limiting step.

Intermolecular Carbonyl–olefin Metathesis with Vinyl Ethers Catalyzed by Homogeneous and Solid Acids in Flow

The carbonyl–olefin metathesis reaction has experienced significant advances in the last seven years with new catalysts and reaction protocols. However, most of these procedures involve soluble catalysts for intramolecular reactions in batch. Herein, we show that recoverable, inexpensive, easy to handle, non-toxic, and widely available simple solid acids, such as the aluminosilicate montmorillonite, can catalyze the intermolecular carbonyl–olefin metathesis of aromatic ketones and aldehydes with vinyl ethers in-flow, to give alkenes with complete trans stereoselectivity on multi-gram scale and high yields. Experimental and computational data support a mechanism based on a carbocation-induced Grob fragmentation. These results open the way for the industrial implementation of carbonyl–olefin metathesis over solid catalysts in continuous mode, which is still the origin and main application of the parent alkene–alkene cross-metathesis.

Highly enantioselective and anti -diastereoselective catalytic intermolecular glyoxylate-ene reactions: Effect of the geometrical isomers of alkenes

An efficient method for the synthesis of homoallylic alcohols with high enantioselectivities and anti-diastereoselectivities via an In(III)-catalyzed intermolecular glyoxylate-ene reaction has been developed. The geometrical isomers of alkenes were shown to have different reactivities. Only the isomers of the alkenes having a proton β-cis to the substituent reacted in this catalytic system.

Palladium-catalyzed asymmetric hydrovinylation under mild conditions using monodentate chiral spiro phosphoramidite and phosphite ligands

Palladium complexes of chiral spiro phosphoramidite and phosphite ligands are effective catalysts in the asymmetric hydrovinylation of vinylarenes with ethylene. The hydrovinylation products were obtained in modest selectivity with enantioselectivities up to 92% ee. The structures of the palladium catalysts have been analyzed by X-ray diffraction. The active catalyst contained one monodentate ligand. A kinetic resolution accompanied the isomerization of the hydrovinylation product in the reaction.

Synthesis of 5-Oxalaurene, 5-Oxaepilaurene and 5-Oxaisolaurene via Radical Cyclisation Reaction

A short synthesis to 5-oxa analogs of the sesquiterpenoids, laurene (3a), epilaurene (3b) and isolaurene (4) using the radical cyclisation reaction as the key step is described.