22089-86-7

Upstream product

• 22089-85-6 1-Acetoxy-1-phenylheptanon-⁽²⁾ 
• 14374-45-9 1-heptynylbenzene 
• 1602573-13-6 (Z)-methyl (1-oxo-1-phenylhept-2-en-2-yl)carbonate 
• 1602573-82-9 methyl (1-phenylhept-1-yn-3-yl)carbonate 
• 536-74-3 phenylacetylene 
• 110-62-3 pentanal 
• 72206-40-7 1-phenylhept-1-yn-3-ol 
• 1074-12-0 phenylglyoxal hydrate 
• 628-05-7 1-nitropentane 
• 55846-68-9 1-phenyl-1,3-octanedione 
• 62059-61-4 1-phenyl-1-octyn-3-one 
• 27259-10-5 1-phenyloct-2-yn-1-one 
• 1671-75-6 Heptanophenone 
• 1638-63-7 2-acetoxy-2-phenylacetyl chloride 

Downstream Products

• 1602573-52-3 2-butyl-5-hydroxy-3-methyl-5-phenylcyclopent-2-enone 

Relevant academic research and scientific papers

Catalyst-Free and Transition-Metal-Free Approach to 1,2-Diketones via Aerobic Alkyne Oxidation

A catalyst-free and transition-metal-free method for the synthesis of 1,2-diketones from aerobic alkyne oxidation was reported. The oxidation of various internal alkynes, especially more challenging aryl-alkyl acetylenes, proceeded smoothly with inexpensive, easily handled, and commercially available potassium persulfate and an ambient air balloon, achieving the corresponding 1,2-diketones with up to 85% yields. Meanwhile, mechanistic studies indicated a radical process, and the two oxygen atoms in the 1,2-diketons were most likely from persulfate salts and molecular oxygen, respectively, rather than water.

Copper/Iodine-Cocatalyzed C-C Cleavage of 1,3-Dicarbonyl Compounds Toward 1,2-Dicarbonyl Compounds

A new, general oxidative route to transformations of 1,3-dicarbonyl compounds to 1,2-dicarbonyl compounds by merging copper and I2 catalysis is described. This method is applicable to broad 1,3-dicarbonyl compounds, including 1,3-diketones, 1,3-keto esters and 1,3-keto amides. Mechanistical studies show that the reaction is achieved via the C–C bond cleavage and CO release cascades.

Dimethyl Sulfoxide as an Oxygen Atom Source Enabled Tandem Conversion of 2-Alkynyl Carbonyls to 1,2-Dicarbonyls

A tandem transformation of 2-alkynyl carbonyl compounds by means of a CuBr2/I2/DMSO/water system is developed, enabling the fromation of various functionalized 1,2-dicarbonyl compounds, including 1,2-diketones, α-keto amides and α-keto ester. This Cu-promoted iodine-mediated tandem procedure employs DMSO as the oxygen atom source of the formed carbonyl group through iodonium ion formation, nucleophilic DMSO addition and C?C bond cleavage cascades. (Figure presented.).

Nitroaldol (Henry) reaction of 2-oxoaldehydes with nitroalkanes as a strategic step for a useful, one-pot synthesis of 1,2-diketones

The nitroaldol (Henry) reaction of 2-oxoaldehydes with a variety of nitroalkanes, under basic heterogeneous conditions and microwave irradiation, affords 1,2-diketones in a one-pot way. The key step of the process involves the nitrous acid elimination fro

Gold-catalyzed oxidative reactions of propargylic carbonates involving 1,2-carbonate migration: Stereoselective synthesis of functionalized alkenes

A gold-catalyzed oxidative reaction of propargylic carbonates or acetates using 3,5-dichloropyridine as the oxidant has been developed. The reaction provides efficient access to α-functionalized-α,β-unsaturated ketones with excellent regio- and diastereoc

Catalytic oxidation of silyl enol ethers to 1,2-diketones employing nitroxyl radicals

A novel and efficient method for the preparation of 1,2-diketones is reported. A series of -diketones were readily prepared by the nitroxyl-radical-catalyzed oxidation of silyl enol ethers using magnesium monoperoxyphthalate hexahydrate (MMPP6H) as the co-oxidant. Georg Thieme Verlag Stuttgart · New York.

A Highly Efficient Ruthenium-Catalyzed Rearrangement of α,β-Epoxyketones to 1,2-Diketones

TpRuPPh3(CH3CN)2PF6 catalyzed the efficient rearrangement of α,β-epoxyketones to 1,2-diketones. Unlike a previously reported iron catalyst, the reaction in this case is applicable not only to 1,2-disubstituted epoxides but also to mono- and trisubstituted epoxides and tolerates oxygen functionalities. The sterically crowded and highly basic tris(1-pyrazolyl)borate (Tp) ligand of the ruthenium catalyst might account for its high selectivity toward 1,2-diketone rather than 1,3-diketone.

Novel and Facile Syntheses of Alkenyl, Alkynyl, and Aryl 1,2-Diketones

Novel and facile routes to alkenyl, alkynyl, and aryl 1,2-diketones utilize treatment of benzotriazole derivatives 1, 7a,b, and 15a-d with butyllithium and subsequent reaction with esters or acid chlorides to yield the substituted intermediates 2a-d, 8a,b, and 16a-g, Reactions of the deprotonated 1 and 7 with α,β-unsaturated aldehydes followed by oxidation also produces similar intermediates 5 and 11a,b. Subsequent hydrolyses of the intermediates of type 2, 5, 8,11, and 16 afford diverse 1,2-diketones in good yields.

Ru-Catalyzed Oxidation of Acetylenes to α-Diketones with Iodosylbenzene

Disubstituted acetylenes are oxidized with PhIO in presence of Ru-catalysts to afford α-diketones in 65-68percent yield.Under the same conditions terminal acetylenes are cleaved to carboxylic acids.