135381-46-3

Upstream product

• 119-67-5 o-carboxybenzaldehyde 
• 84761-77-3 2-formylphenyl triflate 
• 3218-36-8 4-Phenylbenzaldehyde 
• 77308-54-4 2-([1,1'-biphenyl]-4-ylmethyl)benzoic acid 
• 80975-11-7 3-(4-biphenylyl)-3-chlorophthalide 
• 42797-18-2 2-(4-phenylbenzoyl)benzoic acid 
• 4122-56-9 methyl o-formylbenzoate 
• 3315-91-1 4-biphenylylmagnesium bromide 
• 5122-94-1 4-biphenylboronic acid 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 92-52-4 biphenyl 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 610-94-6 2-bromobenzoic acid methyl ester 

Downstream Products

• 72006-57-6 2-phenyl-9,10-dihydroanthracene 
• 1401613-64-6 C₃₄H₃₆O₄S 
• 1401614-12-7 biphenyl-4-yl(2-(thiophen-2-carbonyl)phenyl)methanone 
• 1401613-61-3 C₃₃H₃₆O₅S 
• 1401613-74-8 C₃₆H₃₈O₄ 
• 1401614-15-0 (2-benzoylphenyl)(biphenyl-4-yl)methanone 
• 1401613-73-7 C₃₇H₄₀O₄ 
• 1276042-03-5 biphenyl-4-yl(2-(4-methylbenzoyl)phenyl)methanone 
• 1401614-41-2 C₂₄H₁₆OS 

Relevant academic research and scientific papers

Synthesis of phthalide derivatives using nickel-catalyzed cyclization of o-haloesters with aldehydes

The reaction of o-bromobenzoate (1b) with benzaldehyde (2a) in the presence of [NiBr2(dppe)] (dppe = 1,2-bis(diphenylphosphino)ethane) and zinc powder in THF (24 hours, reflux temperature), afforded 3-phenyl-3H- isobenzofuran-1-one (3a) in an 86% yield. Similarly, o-iodobenzoate reacts with 2a to give 3a, but in a lower yield (50%). A series of substituted aromatic and aliphatic aldehydes (2b, 4-MeC6H4CHO; 2c, 4-MeOC 6H4CHO; 2d, 3-MeOC6H4-CHO 2e, 2-MeOC6H4-CHO; 2f, 4-CNC6H4CHO; 2g, 4-(Me)3-CC6H4CHO; 2h, 4-C6H 4C6H4CHO; 2i, 4-ClC6H 4CHO; 2j, 4-CF3C6H4CHO; 2k, CH 3(CH2)5CHO; 21, CH3(CH 2)2-CHO) also underwent cyclization with o-bromobenzoate (1b) producing the corresponding phthalide derivatives in moderate to excellent yields and with high chemoselectivity. Like 1b, methyl 2-bromo-4,5- dimethoxybenzoate (1c) reacts with tolualdehyde (2b) to give the corresponding substituted phthalide 3m in a 71% yield. The methodology can be further applied to the synthesis of six-membered lactones. The reaction of methyl 2-(2-bromophenyl)acetate (1d) with benzaldehyde under similar reaction conditions afforded six-membered lactone 3o in a 68% yield. A possible catalytic mechanism for this cyclization is also proposed.

Efficient One-Pot Synthesis of 3-Substituted Phthalides via Additive Arylation of Organozinc Intermediate

In recent years, substitution at the third position on phthalides has been proven a valua-ble synthetic intermediate for developing active molecules. We reported a direct and efficient one-pot method for the synthesis of 3-aryl Phthalides performed by adding organo-zinc reagent on methyl-2-formylbenzoate; reagent formed in-situ by the reaction between diethylzinc and different aryl boronic acid derivatives without using any ligand. The possible mechanism involved a coordi-nated zinc carbonyl transition state, arylation, and followed by the intramolecular cyclization. The substituents groups in boronic having different electronic and steric properties played an important role in the reaction completion time and yield. The structure elucidation and confirmation of the synthesized compounds were done by using H-NMR analytical data. The method can be useful for synthesizing various scaffolds and intermediates in search of potentially active compounds.

Direct and selective synthesis of 3-arylphthalides via nickel-catalyzed aryl addition/intramolecular esterification

Herein we report a nickel-catalyzed aryl addition/intramolecular esterification in a cascade fashion. Under the combination of commercially available nickel precursor and tridentate ligand, the one pot protocol offers a direct, simple and regioselective approach to access 3-aryl phthalide derivatives from two readily available substrates with good efficiency, broad scope as well as satisfactory functional group compatibility.

Ni(0)-Catalyzed Dimerization of o-Keto Carboxylic Acid Pseudochlorides

A new protocol of the synthesis of 3,3′-diaryl-3,3′-diphthalides by dehalogenation of o-keto carboxylic acid pseudochlorides is implemented. The feature of the new protocol is that the reaction is carried out in the presence of a zero-valent nickel comple

Metal-Free Aerobic Oxidative C–O Coupling of C(sp3)–H with Carboxylic Acids Catalyzed by DDQ and tert-Butyl Nitrite

The formation of the C–O bond is one of the hot topics in the area of C(sp3)–H bond functionalization. A metal-free oxidative cross-coupling between benzylic C(sp3)–H bond and carboxylic acids has been developed. The reactions were performed with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as the catalyst, tert-butyl nitrite (TBN) as the co-catalyst, and molecular oxygen as the terminal oxidant. A variety of diarylmethanes could be successfully coupled with various carboxylic acids to obtain diarylmethanol esters in good to excellent yields. In addition, 2-benzylbenzoic acids could be converted into phthalides in moderate yields through an intramolecular oxidative cyclization.

Catalytic asymmetric synthesis of 3-aryl phthalides enabled by arylation-lactonization of 2-formylbenzoates

The catalytic asymmetric synthesis of 3-aryl phthalides is reported through a sequential asymmetric arylation-lactonization reaction. The reaction is enabled by a boron-zinc exchange to generate reactive arylating agents, which react with 2-formylbenzoates in the presence of a chiral amino naphthol ligand. The enantiodetermining step is the arylation of the aldehyde, which then undergoes a lactonization event to yield the corresponding phthalides in good yields and enantioselectivities.

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.

Efficient synthesis of 3-arylphthalides using palladium-catalyzed arylation of aldehydes with organoboronic acids

(Chemical Equation Presented) The synthesis of 3-arylphthalides via palladium-catalyzed arylation of aldehydes with organoboronic acids was achieved using the thioether-imidazolinium carbene ligand in good to excellent yields and was carried out using 1.0

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.