90909-58-3

Upstream product

• 108990-10-9 2-chloro-6H-benzo[c]benzopyran 
• 16231-67-7 methyl 2'-formyl-[1,1'-biphenyl]-2-carboxylate 
• 106-48-9 4-chloro-phenol 
• 112-36-7 3,6,9-trioxaundecane 
• 124137-66-2 bis-(2-chloro-6H-benzo[c]chromen-6-yl)-peroxide 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 2516-95-2 5-chloro-2-nitrobenzoic acid 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 63503-60-6 3-chlorophenylboronic acid 
• 773134-22-8 C₁₄H₁₁ClO₂ 
• 607-12-5 5-chloro-biphenyl-2-ol 
• 201230-82-2 carbon monoxide 
• 1184761-62-3 2-(5-chloro-2-methoxyphenyl)benzaldehyde 
• 1181344-87-5 2-(5-chloro-2-methoxyphenyl)benzoic acid 

Downstream Products

• 119338-10-2 2-chloro-6,6-diphenyl-6H-benzo[c]chromene 
• 114508-05-3 5-chloro-2-(4-nitro-benzoyloxy)-2'-(4-nitro-benzoyloxymethyl)-biphenyl 

Relevant academic research and scientific papers

Cerium Ammonium Nitrate-Mediated Access to Biaryl Lactones: Substrate Scopes and Mechanism Studies

Herein we described an access to biaryl lactones from ortho-aryl benzoic acids via intramolecular O-H/C-H oxidative coupling with the commonly used cerium ammonium nitrate (CAN) as the one-electron oxidant under a thermal condition. The radical interrupting experiment suggested a radical process, while the kinetic isotope effect (KIE) showed that the C-H cleavage likely was not involved in the rate-determining step. Competitive reactions, especially the strikingly different ρ values of Hammett equations, indicated that the reaction rate was more sensitive to the electronic properties on the aryl moiety rather than the carboxylic moiety, which corresponded to the first single electron transfer (SET) step. In addition, the quite negative ρ values (-4.7) of the aryl moiety unveiled the remarkable electrophilic nature of the second intramolecular radical addition process, which was also consistent with product yields and regioselectivity. Moreover, control experiments disclosed that the single electron in the third step was also transferred to CeIV instead of molecular oxygen. Besides, the possible role of co-solvents trifluoroethanol (TFE) and its influences on the CeIV species were discussed. This work elucidated the possible mechanism by proposing the step that had more effects on the total reaction rate and the species that was responsible for the last single electron transfer.

3, 4-benzocoumarin derivative as well as preparation method and application thereof

The general formula of the 3, 4-benzocoumarin derivative is shown as a formula I, and definitions of substituent groups are shown in the specification in detail. The 3, 4-benzocoumarin derivative witha novel structure provided by the invention is simple in preparation method, nontoxic and harmless, has blue fluorescence, and can be used as a potential organic functional material. The structure ofthe compound has modifiability, and has high optical stability and thermal stability.

Palladium-Catalyzed Site-Selective Benzocylization of Aromatic Acids with o-Fluoro-Substituted Diaryliodonium Salts toward 3,4-Benzocoumarins

By using 2-fluoro-substituted diaryliodonium salts, a novel benzocylization has been accomplished for the synthesis of 3,4-benzocoumarin derivatives via a cascade of ortho-arylation and defluorination in the presence of palladium catalysts. The reaction exhibits a broad compatibility of readily available aromatic acids with an excellent level of site-selectivity. Mechanistic investigations revealed a unique reactivity of carboxylic acid directed arylation by followed nucleophilic substitution of aromatic fluoride in the present system.

Cerium photocatalyzed dehydrogenative lactonization of 2-arylbenzoic acids

The first cerium photocatalyzed dehydrogenative lactonization of 2-arylbenzoic acids has been developed. This operationally simple protocol allows rapid access to synthetically useful coumarins on gram scale by employing CeCl3 as a photocatalyst and O2 as a terminal oxidant. Overall, this delivers an economical and environmentally amiable entry to diversely substituted coumarins, important structural motifs in bioactive molecules.

Microwave-assisted cyclization under mildly basic conditions: Synthesis of 6 h -benzo [c] chromen-6-ones and their 7,8,9,10-tetrahydro analogues

Aryl 2-bromobenzoates and aryl 2-bromocyclohex-1-enecarboxylates are cyclized by microwave irradiation in dimethylformamide in the presence of K2CO3 to give the corresponding 6H-benzo[c]chromen-6-ones and their 7,8,9,10-tetrahydro analogues, respectively, in 50-72% yields. Aryl 3-bromoacrylates are also converted into 2H-chromen-2-ones under the employed conditions.

Scalable Electrochemical Dehydrogenative Lactonization of C(sp2/sp3)-H Bonds

A practical, electrochemical method is developed for the direct dehydrogenative lactonization of C(sp2/sp3)-H bonds under external oxidant- and metal-free conditions, delivering diverse lactones, including coumarin derivatives with excellent regioselectivity. The scalable nature of this newly developed electrochemical process was demonstrated on a 40 g scale following an operationally simple protocol. The remote lactonization of C(sp3)-H bonds would constitute an important synthetic advance toward electrochemical C-O bond formation.

Organocatalytic Electrochemical C-H Lactonization of Aromatic Carboxylic Acids

An electrochemical strategy has been developed for radical arene carbon-oxygen bond formation. This reaction utilizes DDQ as a redox mediator, with inexpensive glassy carbon electrodes to facilitate an intramolecular lactonization of biphenyl-2-carboxylic

Electrochemical C?O Bond Formation: Facile Access to Aromatic Lactones

An efficient and robust methodology based on electrochemical techniques for the direct synthesis of aromatic lactones through dehydrogenative C?O cyclization is described. This new and useful electrochemical reaction can tolerate a variety of functional groups, and is scalable to 100 g under mild conditions. Remarkably, heterocycle-containing substrates can be employed, thus expanding the scope of radical C?O cyclization reactions.

Palladium-Catalyzed Direct Annulation of Benzoic Acids with Phenols to Synthesize Dibenzopyranones

Direct annulation of benzoic acids with phenols via palladium-catalyzed oxidative coupling is reported. Readily available and inexpensive starting materials were used in this novel method to synthesize highly valuable and useful dibenzopyranone scaffolds.

[N,P]-pyrrole PdCl2 complexes catalyzed the formation of dibenzo-α-pyrone and lactam analogues

We herein report the synthesis and catalytic application of a new family of [N,P] ligands based on the pyrrole ring with alpha-phosphine or phosphole units. Their palladium complexes (3a-d) were obtained in very good yields and their catalytic properties were evaluated in the direct intramolecular arylation to obtain both benzopyranones and phenanthridinones. The air stable complex 3a exhibited the best catalytic performance of this series of complexes, using 1 mol% of catalyst in combination with microwaves to promote this reaction.