128174-46-9

Upstream product

• 188716-95-2 3-(2-Chloro-2-phenyl-ethyl)-3H-isobenzofuran-1-one 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 104-55-2 3-phenyl-propenal 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 98-86-2 acetophenone 
• 119-67-5 o-carboxybenzaldehyde 
• 88070-48-8 N-methylbenzamide 
• 188716-83-8 3-(2-hydroxy-2-phenylethyl)isobenzofuran-1(3H)-one 
• 13203-89-9 3-phenacylphthalide 
• 380430-53-5 2-(ethoxycarbonyl)phenylboronic acid 
• 269409-99-6 ethyl 2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoate 
• 104-54-1 3-Phenylpropenol 
• 103-54-8 cinnamyl acetate 

Downstream Products

• 1459243-96-9 (Z)-3-(2-phenylethylidene)isobenzofuran-1(3H)-one 

Relevant academic research and scientific papers

Practical synthesis of 3-(2-arylethylidene)isoindolin-1-ones (analogues of AKS-182) and 3-(2-arylethylidene)isobenzofuran-1(3H)-ones

A simple and practical method is reported for the synthesis of 3-(2-arylethylidene)isoindolin-1-ones and 3-(2-arylethylidene)isobenzofuran-1(3H)-ones, proceeding with good to excellent yields and (E:Z) selectivity. This methodology involves the sequential reduction-dehydration reaction of readily obtained 3-(2-oxo-2-arylethyl)isoindolin-1-ones and 3-(2-oxo-2-arylethyl)isobenzofuran-1(3H)-ones followed by a base-catalyzed double bond isomerization with K2CO3 in acetonitrile. The development of a concise synthesis of AKS-182 has been achieved using this methodology.

Selenium-catalyzed C(sp3)-H acyloxylation: Application in the expedient synthesis of isobenzofuranones

Oxidative Se-catalyzed C(sp3)-H bond acyloxylation has been used to construct a diverse array of isobenzofuranones from simple ortho-allyl benzoic acid derivatives. The synthetic procedure employs mild reaction conditions and gives high chemoselectivity enabled by an inexpensive organodiselane catalyst. The presented approach offers a new synthetic pathway toward the core structures of phthalide natural products.

Synthesis of biarylketones and phthalides from organoboronic acids and aldehydes catalyzed by cobalt complexes

A cobalt-catalyzed addition of aryl- and alkenylboronic acids to aldehydes and phthalaldehyde to give the corresponding biarylketones and 3-aryl phthalides in good to excellent yields in one pot is described.

Rhodium or palladium-catalyzed cascade aryl addition/intramolecular lactonization of phthalaldehydonitrile to access 3-aryl and 3-alkenyl phthalides

A rhodium or palladium-catalyzed addition of boronic acids to phthalaldehydonitrile, followed by an intramolecular lactonization of cyano to access 3-substituted phthalides, is described. This procedure tolerates a series of functional groups, such as methoxy, fluoro, chloro, and vinyl groups. It is a novel procedure for the synthesis of 3-arylphthalides.

Rhodium-catalyzed cascade reaction: Aryl addition/intramolecular esterification to access 3-aryl and 3-alkenyl phthalides

Chemical Equation Reprentation First one and then the other: A rhodiumcatalyzed addition of aryl and alkenyl boronic acids to phthalaldehyde and subsequent intramolecular esterification is described (see scheme; cod = l,5-cyclooctadiene, dppb = 1,4-bis(diphenylphosphino)butane). The method is facile and practical for accessing 3-aryl and 3-alkenyl phthalides in moderate to good yields. Several functional groups are tolerated under the reaction conditions.

Palladium-catalyzed cascade aryl addition/intramolecular lactonization of phthalaldehyde to access 3-aryl- and alkenylphthalides

A palladium-catalyzed addition of arylboronic acids to phthalaldehyde, followed by an intramolecular lactonization to access 3-substituted phthalides, is described. The procedure tolerates a series of functional groups, such as methoxyl, fluoro, chloro, and trifluoromethyl groups. It represents a procedure for the synthesis of 3-substituted phthalides.

Highly efficient cyclization of o-iodobenzoates with aldehydes catalyzed by cobalt bidentate phosphine complexes: A novel entry to chiral phthalides

Methyl 2-iodobenzoates 1a-c undergo cyclization reactions with various aromatic aldehydes 2a-m (RC6CHO: R = H 2a, 4-CH3, 2b, 4tBu 2c, 4-OMe 2d, 3-OMe 2e, 4-C1 2f, 4-CF3 2g, 4-CN 2h, 4-Ph 2i; benzo [d][1,3]dioxole-5-carbaldehyde (2j), 1napthaldehyde (2k), benzofuran-2- carbaldehyde (21), and isonicotinaldehyde (2m)) in the presence of [CoI2(dppe)] (dppe = l,2-bis(diphenylphosphino)ethane) and Zn powder in dry THF at 75 °C for 24 h to give the corresponding phthalide derivatives 3a-m and 3q-t in good to excellent yields. Under similar reaction conditions, less reactive aliphatic aldehydes, heptanal (2n), butyraldehyde (2o), and 2-phenylacetaldehyde (2p) also underwent cyclization reactions with la to provide 3n-p, respectively, in fair to good yields. The catalytic reaction can be further extended to cinnamyl aldehyde (2q) with la to give the corresponding phthalide derivative 3u. This synthetic method is compatible with a variety of functional groups on the aryl ring of 2. The high efficiency of the cobalt catalyst containing a dppe (dppe = l,2-bis(diphenylphosphino)ethane) ligand encouraged us to investigate the asymmetric version of the present catalytic reaction by employing bidentate chiral ligands. Thus, aromatic aldehydes 2a-c, 2f, and 2 g undergo cyclization with 2-iodobenzoate (la) smoothly in the presence of [CoI2{(S,S)- dipamp}] ((S,S)-dipamp = (1S,2S)-(+)-bis[2-methoxyphenyl]phenylphosphino)ethane) and zinc powder in THF at 75 °C for 24 h, giving the corresponding (S)-phthalides 4a-e in 8189 % yields with 70-98 % ee. A possible mechanism for the present catalytic reaction is proposed.