107733-24-4

Upstream product

• 6295-21-2 3-chloro-1(3H)-isobenzofuranone 
• 91-20-3 naphthalene 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 5018-87-1 2-(naphthalene-1-carbonyl)-benzoic acid 
• 66-77-3 1-naphthaldehyde 
• 119-67-5 o-carboxybenzaldehyde 
• 69238-67-1 o-<(1-naphthyl)methyl>benzoic acid 
• 90-11-9 1-Bromonaphthalene 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 85-44-9 phthalic anhydride 
• 13922-41-3 1-Naphthylboronic acid 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 4122-56-9 methyl o-formylbenzoate 
• 703-55-9 1-naphthylmagnesiumbromide 

Downstream Products

• 81830-45-7 o-<(4-bromo-1-naphthyl)methyl>benzoic acid 
• 81830-46-8 o-<(4-bromo-1-naphthyl)methyl>benzoic acid chloride 
• 81830-47-9 o-<(4-bromo-1-naphthyl)methyl>acetophenone 
• 107796-85-0 (R)-(-)-3-(1-naphthyl)phthalide 
• 69238-67-1 o-<(1-naphthyl)methyl>benzoic acid 

Relevant academic research and scientific papers

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.

Rhenium-Catalyzed Phthalide Synthesis from Benzamides and Aldehydes via C-H Bond Activation

The [4 + 1] annulation of benzamides and aldehydes for phthalide synthesis was achieved via rhenium-catalyzed C-H activation, which demonstrates an unprecedented reaction pattern distinct from those of other transition-metal catalyses. The reaction also features readily available starting materials, a wide scope for both electro-rich and electro-deficient substrates, and the elimination of homoannulation byproducts.

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 or palladium-catalyzed cascade aryl addition/ intramolecular lactonization of phthalaldehyde with potassium organotrifluoroborates to access 3-arylphthalides

An efficient rhodium-catalyzed lactonization of phthalaldehyde with potassium organotrifluoroborates to access 3-arylphthalides has been developed. Moreover, palladium is a also good catalyst for such transformation.

Transition metal-catalyzed addition reactions of arylboronic acids with alkyl 2-formylbenzoates: Efficient access to chiral 3-substituted phthalides

Transition metal-catalyzed addition of arylboronic acids to 2-formylbenzoates afforded 3-substituted phthalides. By using SPINOL-based phosphites as ligands, a Rh(i)-catalyzed asymmetric version of such an addition reaction was achieved. The Royal Society of Chemistry 2010.

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.

Synthesis and characterization of benzannelated thienyl oligomers

An array of 1,3-diarylbenzo[c]thiophenes have been synthesized by the ring-opening of lactones followed by thionation using Lawesson's reagent with concurrent intramolecular cyclization. Photophysical studies of the various benzo[c]thiophene analogues are presented. The results of a cyclic voltammetric investigation of the benzo[c]thiophenes are also reported.

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.

Synthesis of 1,3-diaryl benzo[c]thiophenes

An array of 1,3-diarylbenzo[c]thiophenes has been synthesized via the ring opening of lactones followed by thionation using Lawesson's reagent.