1283669-54-4

Upstream product

• 943835-77-6 5-fluoro-2-(2-phenylethynyl)benzaldehyde 
• 94569-84-3 2-bromo-5-fluorobenzaldehyde 
• 536-74-3 phenylacetylene 
• 1382353-01-6 C₁₅H₁₀FIO₂ 
• 1647071-70-2 2-((2-phenyl)ethynyl)-5-fluorobenzoic acid methyl ester 
• 455-38-9 3-fluorobenzoic acid 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 1864-94-4 phenyl formate 
• 1274058-51-3 C₁₄H₁₀BrFO 

Relevant academic research and scientific papers

Modular synthesis of 3-substituted isocoumarinsviasilver-catalyzed aerobic oxidation/6-endoheterocyclization ofortho-alkynylbenzaldehydes

A method involving silver-catalyzed aerobic oxidation/6-endoheterocyclization ofortho-alkynylbenzaldehydes to yield 3-substituted isocoumarins is described. The developed protocol allows convenient access to a range of synthetically useful 3-substituted isocoumarins and related fused heterocyclolactones in good to high yields, using silver tetrafluoroborate as the catalyst, and atmospheric oxygen as the terminal oxidant and the source of endocyclic oxygen. Mechanistic studies suggest the involvement of a free-radical pathway.

Method for synthesizing isocoumarin derivative under catalysis of silver and application of isocoumarin derivative

The invention belongs to the technical field of organic synthetic chemistry, and particularly relates to a method for synthesizing an isocoumarin derivative under catalysis of silver and application of the isocoumarin derivative. According to the method, 2-(phenylethynyl)benzaldehyde is taken as a model substrate, monovalent silver salt is taken as a catalyst, reaction is carried out at the temperature not lower than 30 DEG C, and the isocoumarin derivative is generated. In the field, 2-(phenylethynyl)benzaldehyde is used as a model substrate for the first time, and the isocoumarin derivative is prepared in one step under the catalytic action of the monovalent silver salt. The method is simple, convenient and efficient, the used raw materials are simple, easy to obtain and non-toxic, the steps are few, the conditions are mild, the cost is low, and the method is suitable for large-scale industrial production.

Lactonization of 2-Alkynylbenzoates for the Assembly of Isochromenones Mediated by BF3·Et2O

A general and efficient lactonization method of readily available 2-alkynylbenzoates affording biologically important isochromenones has been realized via a solely BF3·Et2O-mediated 6-endo-dig cyclization process under mild condition

Palladium-Catalyzed Sequential Nucleophilic Addition/Oxidative Annulation of Bromoalkynes with Benzoic Acids to Construct Functionalized Isocoumarins

An efficient and robust protocol for the preparation of 3-substituted isocoumarins via palladium-catalyzed nucleophilic addition/oxidative annulation of bromoalkynes with benzoic acids has been developed. Remarkably, preliminary mechanistic studies indicated that the transformation might proceed via a stereo- and regioselective nucleophilic addition and C-H functionalization procedure.

Palladium-catalyzed carbonylative synthesis of isocoumarins and phthalides by using phenyl formate as a carbon monoxide source

A simple and efficient palladium-catalyzed intramolecular carbonylative synthesis of isocoumarins and phthalides from the easily available starting materials by employing phenyl formate as a CO surrogate has been achieved. The approach affords target compounds in good to excellent yields with the advantages of lower toxicity, milder conditions, easy operation and wide functional group tolerance.

New method for the synthesis of lactones via nickel-catalyzed isocyanides insertion

A novel nickel catalyst for the reaction of tert-butyl isocyanide insertion was discovered. In this approach, 1,2-bis(diphenylphosphino)ethane (L3) serves as an efficient ligand, thereby allowing the preparation of lactones from (o-bromophenyl)phenylethanone derivatives. It is noteworthy that this is the first example of nickel acting as a metal catalyst in the reactions of tert-butyl isocyanide insertion. The significance of this methodology may draw many chemists attention in the field of isocyanide-incorporating reactions. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Palladium-catalyzed synthesis of isocoumarins and phthalides via tert -butyl isocyanide insertion

A novel and highly efficient strategy for the synthesis of isocoumarins and phthalides through a palladium(0)-catalyzed reaction incorporating tert-butyl isocyanide has been developed. This process, providing one of the simplest methods for the synthesis of this class of valuable lactones, involves two steps including cyclization reaction and simple acid hydrolysis. The methodology is tolerant of a wide range of substrates and applicable to library synthesis.

Synthesis of 3-substituted isocoumarins via a cascade intramolecular Ullmann-type coupling-rearrangement process

A simple and highly efficient strategy for the synthesis of 3-substituted isocoumarins through a copper(I)-catalyzed reaction of 1-(2-halophenyl)-1,3- diones has been developed. The procedure is based on a cascade copper-catalyzed intramolecular Ullmann-type C-arylation and rearrangement process. This methodology is tolerant of a wide range of substrates and applicable to library synthesis.

NHC-catalyzed oxidative cyclization reactions of 2-alkynylbenzaldehydes under aerobic conditions: Synthesis of O-Heterocycles

Chemical equations presented. An NHC-catalyzed, regio- and stereoselective oxidative cyclization of o-alkynylbenzaldehydes bearing an unactivated alkyne moiety as an internal electrophile has been developed to afford phthalides and isocoumarins. A single organocatalytic system enabled two sequential C-O bond formations to take place in an atom economical manner via highly efficient dual activation. Molecular oxygen in air could be utilized as a source of an oxygen atom for the oxidation of aldehydes to the corresponding benzoic acids under our newly developed reagent system.