57193-24-5

Upstream product

• 601-84-3 2,6-dibromobenzoic acid 
• 65-85-0 benzoic acid 
• 532-32-1 sodium benzoate 
• 50-30-6 2,6-dichlorobenzoic acid 
• 98-88-4 benzoyl chloride 
• 33757-48-1 N-quinolin-8-yl-benzamide 

Downstream Products

• 76900-72-6 <2,4-2H2>-3-methylcyclohexa-1,4-diene 
• 757959-85-6 methyl 2,6-dideuteriobenzoate 
• 112484-79-4 2,6-dideuterio-benzoyl chloride 

Relevant academic research and scientific papers

Directing-Group-Controlled Ring-Opening Addition and Hydroarylation of Oxa/azabenzonorbornadienes with Arenes via C-H Activation

An efficient method for the directing group controlled rhodium-catalyzed addition reaction of oxa/azabicylic alkenes with aromatic ketones and benzoic acids has been developed. The ketones and benzoic acids afforded different addition products when reacte

IrIII-Catalyzed Selective ortho-Monoiodination of Benzoic Acids with Unbiased C?H Bonds

An iridium-catalyzed selective ortho-monoiodination of benzoic acids with two equivalent C?H bonds is presented. A wide range of electron-rich and electron-poor substrates undergo the reaction under mild conditions, with >20:1 mono/di selectivity. Importantly, the C?H iodination occurs selectively ortho to the carboxylic acid moiety in substrates bearing competing coordinating directing groups. The reaction is performed at room temperature and no inert atmosphere or exclusion of moisture is required. Mechanistic investigations revealed a substrate-dependent reversible C?H activation/protodemetalation step, a substrate-dependent turnover-limiting step, and the crucial role of the AgI additive in the deactivation of the iodination product towards further reaction.

Switchable C?H Alkylation of Aromatic Acids with Maleimides in Water: Carboxyl as a Diverse Directing Group

A ruthenium-catalyzed protocol to access conjugate addition or decarboxylative conjugate addition of aromatic acids with maleimides has been developed. The reaction shows interesting chemoselectivity with different substituted benzoic acids. The reaction pathway of C?H alkylation is controlled by the intrinsic property of aromatic acids but not reaction conditions. Under almost the same reaction conditions, carboxyl can act as either a classical directing group or a traceless directing group, thereby generating two kinds of products, i. e., 2-alkyl substituted benzoic acids and alkyl substituted benzenes. These two reactions proceeded under mild and redox-neutral conditions in neat water under the atmosphere of air, and could be easily scaled up to grams. The decarboxylative conjugate addition, where carboxyl acts as a traceless directing group, can be realized without the addition of any ligand, silver or copper salt.

Divergent Synthesis of Isoquinolone and Isocoumarin Derivatives by the Annulation of Benzoic Acid with N-Vinyl Amide

A simple and efficient method for the synthesis of isoquinolone and isocoumarin derivatives is reported. The method for the first time provides a one-step divergent synthesis of important isoquinolone and isocoumarin skeletons from benzoic acid by switching the coupling partners. In addition, a reliable mechanism has been proposed on the basis of experimental investigations, including kinetic isotope effect experiments, 13C labeling experiments, time-tracking experiments, and competitive experiments, as well as DFT calculation studies.

Carboxyl-Directed Conjugate Addition of C?H Bonds to α,β-Unsaturated Ketones in Air and Water

A simple ruthenium-catalyzed conjugate addition of C?H bonds to α,β-unsaturated ketones directed by a removable carboxyl group was developed as an effective protocol to synthesize ortho-alkylated benzoic acids in a greener manner. Without any additives, s

Rh(III)-Catalyzed [4 + 2] Self-Annulation of N-Vinylarylamides

An efficient rhodium(III)-catalyzed self-annulation of N-vinylarylamide has been developed. This reaction features a simple system and good reactivity with complete regioselectivity. The protocol provides easy access to an aminal incorporated dihydroisoqu

Palladium-Catalyzed H/D Exchange Reaction with 8-Aminoquinoline as the Directing Group: Access to ortho-Selective Deuterated Aromatic Acids and β-Selective Deuterated Aliphatic Acids

We develop a palladium-catalyzed H/D exchange reaction with 8-aminoquinoline as the directing group as well as D2O as the source of deuterium atom and solvent. This reaction achieves selectively H/D exchange at the ortho-C-H of aromatic amides and the β-C-H of aliphatic amide. Ortho-deuterated aromatic acids and β-deuterated aliphatic acids are obtained by removal of the directing group. And a possible mechanism is also proposed.

Preparation method of o-position deuterated benzoic acid compound

The invention discloses a preparation method of an o-position deuterated benzoic acid compound. The preparation method sequentially comprises the following steps: carrying out an oil bath reaction on8-aminoquinoline substituted benzoic acid amide used as a raw material under a sealing state at a temperature of 120-160 DEG C for 24-72 hours in the presence of a deuterated reagent and a palladium catalyst, cooling the obtained reaction liquid to room temperature, carrying out extraction, washing the obtained organic layer, and carrying out drying and concentration; carrying out silica gel column chromatography on the obtained concentrate; carrying out an oil bath reaction on the obtained deuterated intermediate in a sulfuric acid water solution at 120+/-20 DEG C until a TLC detection reaction is completed; cooling the obtained reaction solution to room temperature, carrying out extraction, washing the obtained ether layer, and carrying out drying, suction filtration and concentration toobtain the o-position deuterated benzoic acid compound. The o-position deuterated benzoic acid compound prepared by adopting the method provided by the invention has the technical advantages of highyield, good selectivity and good economical efficiency.

Burgess iridium(I)-catalyst for selective hydrogen isotope exchange

We have evaluated the commercially available Burgess catalyst in hydrogen isotope exchange reactions with several substrates bearing different directing group functionalities and have obtained moderate to high (50%-97%D) deuterium incorporations. The broa

Rhodium(III)-catalyzed ortho c-h heteroarylation of (hetero)aromatic carboxylic acids: A rapid and concise access to π-conjugated poly-heterocycles

Abstract RhIII-catalyzed oxidative Ci-H/Ci-H cross-coupling between (hetero)aromatic carboxylic acids and various heteroarenes has been accomplished to construct highly functionalized ortho-carboxy-substituted bi(hetero)aryls. The use of a carboxy group as the directing group obviates tedious steps for installation and removal of extra directing groups, and enables a facile one-step synthesis of ortho-carboxy bi(hetero)aryls. The method provides opportunities for rapid assembly of a library of important fluorene and coumarin-type poly-heterocycles through intramolecular electrophilic substitution or oxidative lactonization. As illustrative examples, the strategy developed herein greatly streamlines accesses to a variety of appealing polyheterocycles such as DTPO (5H-dithieno[3,2-b:2',3'-d]pyran-5-one), CPDTO (cyclopentadithiophen-4-one), and indenothiophenes. Under construction: The highly regioselective title reaction directly furnishes ortho-carboxy bi(hetero)aryls. The method has the potential to lead to the rapid construction of a library of appealing poly-heterocycles, given the complete regiocontrol, readily available substrates, and functional-group tolerance.