852525-80-5

Upstream product

• 7154-75-8 4-methylpentyne 
• 100-52-7 benzaldehyde 

Downstream Products

• 65236-44-4 1-phenyl-5-methyl-2-hexyn-1-one 
• 23566-47-4 5-methyl-1-phenyl-hex-1-yn-3-one 
• 1644494-03-0 5-methyl-1-phenylhex-2-yn-1-yl 3,4-dihydro-2H-pyran-6-carboxylate 

Relevant academic research and scientific papers

Rhodium-catalyzed addition of arylzinc reagents to aryl alkynyl ketones: Synthesis of β,β-disubstituted indanones

(Chemical Equation Presented) A rhodium-catalyzed addition of arylzinc reagents to aryl alkynyl ketones for the synthesis of highly substituted indanones has been developed. The key to success has proved to be a proper choice of the reaction system, which involves the employment of dppf as a ligand and 1,2-dichloroethane as a solvent.

Redox-Neutral Arylations of Vinyl Cation Intermediates

Herein we present a new unified concept for C?C bond formation under redox-neutral conditions. Our strategy hinges upon interception of a vinyl cation with a sulfoxide resulting in simultaneous C–C and C?O bond formation and arylation. A range of structurally diverse vinyl cations are generated in situ in the presence of a sulfoxide, resulting in hydrative arylation, direct arylation of enol triflates and interrupted Meyer–Schuster rearrangement. Mechanistic investigations showcase the crucial role played by the fleeting vinyl cation intermediate and structural features that lead to its stabilization. Applications of the reaction products to synthesis are also presented. (Figure presented.).

Dehydrogenative Meyer-Schuster-like rearrangement: A gold-catalyzed reaction generating an alkyne

Easily accessible propargylic esters are converted to the inverted alkynyl ketones in an oxidative gold-catalyzed reaction. Gagosz's catalyst in combination with PhI(OAc)2 is the best system for this conversion and 18 examples with yields up to 80 % are reported. The results indicate that the triple bond in the product is formed by elimination from a vinylgold intermediate. In a formal sense the new conversion overall is a dehydrogenative Meyer-Schuster rearrangement. It takes alkynes: Propargyl esters can be converted into alkynyl ketones by a new oxidative gold-catalyzed reaction. The best catalyst system is Ph3PAuCl/AgNTf2 in combination with the oxidant PhI(OAc)2. The yields are as high as 80 % and the reaction can be conducted in the presence of air. Copyright

Highly diastereoselective synthesis of cyclopentenones via a one-pot gold catalysis, Nazarov cyclization and alkylation cascade

Starting from readily available propargylic carboxylates, three sequential transformations [gold-catalyzed tandem reaction, scandium(III) trifluoromethanesulfonate catalyzed Nazarov cyclization, alkylation reaction] in a one-pot process led to the formation of cyclopentenone derivatives in excellent diastereoselectivities and moderate to good overall yields. Georg Thieme Verlag Stuttgart. New York.