84450-90-8

Upstream product

• 118-90-1 ortho-methylbenzoic acid 
• 16463-31-3 2-methylbenzoic acid potassium salt 
• 1182669-71-1 N-(2-methylbenzoyl)-8-aminoquinoline 
• 933-88-0 ortho-toluoyl chloride 

Downstream Products

• 39627-61-7 7-methyl-1-indanone 

Relevant academic research and scientific papers

Oxazolinyl-Assisted Ru(II)-Catalyzed C-H Allylation with Allyl Alcohols and Synthesis of 4-Methyleneisochroman-1-ones

We report herein a ruthenium-catalyzed, oxazoline-directed strategy for C-H allylation of aryl oxazolines using allylic alcohols as the coupling partner. The present transformation unravels the unusual reactivity of allylic alcohols in the synthesis of 4-

Iridium-Catalyzed, Weakly Coordination-Assisted Ortho-Alkynylation of (Hetero)aromatic Carboxylic Acids without Cyclization

It is reported a weakly coordination-assisted alkynylation of aryl and heteroaryl carboxylic acids with iridium catalysis. The reaction is catalyzed by [{Cpz.ast;IrCl2}2] complex without cyclization, forming ortho-alkynylated aryl and heteroaryl carboxylic acids, and features high functional group tolerance and broad substrate scope under an air atmosphere. 2-(Hetero)aryl-substituted acetic acids were amenable to the alkynylation by forming an unusual six-membered ring cycloiridiated intermediate.

Ruthenium-Catalyzed Alkynylation of Benzoic Acids Mediated by a Weakly Coordination-Directing Auxiliary

A method for the ruthenium-catalyzed ortho-alkynylation of benzoic acids was developed. The reaction was found to be directed by a weakly coordinating carboxyl group and offers a facile route for the synthesis of ortho-alkynylated derivatives. A rare exam

Enhancing Ru(II)-Catalysis with Visible-Light-Mediated Dye-Sensitized TiO2 Photocatalysis for Oxidative C?H Olefination of Arene Carboxylic Acids at Room Temperature

Erythrosine B sensitized TiO2 photocatalysis has been combined with Ru(II)-catalysis to accomplish an oxidative olefination/annulation of benzoic acids with activated olefins under mild conditions that tolerates useful functionalities, such as

A modular biomimetic strategy for the synthesis of macrolide P-glycoprotein inhibitors via Rh-catalyzed C-H activation

One of the key challenges to overcome multidrug resistance (MDR) in cancer is the development of more effective and general strategies to discover bioactive scaffolds. Inspired by natural products, we describe a strategy to achieve this goal by modular biomimetic synthesis of scaffolds of (Z)-allylic-supported macrolides. Herein, an Rh(III)-catalyzed native carboxylic acid-directed and solvent-free C?H activation allylation with high stereoselectivity and chemoselectivity is achieved. The generated poly-substituted allylic alcohol as a multifunctional and biomimetic building block is crucial for the synthesis of (Z)-allylic-supported macrolides. Moreover, the unique allylic-supported macrolides significantly potentiate the sensitivity of tumor cells to cytotoxic agents such as vinorelbine and doxetaxel by reversing p170-glycoprotein-mediated MDR. Our findings will inspire the evolution of synthetic chemistry and open avenues for expedient and diversified synthesis of bioactive macrocyclic molecules.

Ring-Opening Ortho-C-H Allylation of Benzoic Acids with Vinylcyclopropanes: Merging Catalytic C-H and C-C Activation Concepts

A Ru-catalyzed selective and atom-economic ortho-C-H allylation of aromatic acids with vinylcyclopropanes is reported. The reaction proceeds with selective cleavage of both a C-H and a C-C bond. A wide range of allylarenes were synthesized in high yields

Ru-catalyzed (E)-specific ortho-C-H alkenylation of arenecarboxylic acids by coupling with alkenyl bromides

In the presence of [p-cymene)RuCl2]2, (E)-configured alkenyl bromides couple with aromatic carboxylates to form ortho-vinylbenzoic acids. This C-H vinylation proceeds in high yields without any activating phosphine ligands and has an excellent functional group tolerance. Starting from commonly available (E/Z)-mixtures of alkenyl bromides, (E)-configured vinyl arenes or dienes are formed exclusively. Mechanistic studies show that this selectivity is achieved because the (E)-configured alkenyl bromides undergo a smooth coupling, whereas the (Z)-isomers are rapidly eliminated with the formation of alkynes.

2,2′-Biaryldicarboxylate Synthesis via Electrocatalytic Dehydrogenative C-H/C-H Coupling of Benzoic Acids

2,2′-Biaryldicarboxylates are important functionalities in bioactive compounds, functional materials, and chiral catalysts. These compounds have been found to be conveniently accessible from benzoic acids via Rh-catalyzed electrooxidative C-H/C-H couplings, giving valuable dihydrogen as the byproduct. In an undivided cell with Pt electrodes, RhCl3·3H2O catalyzes the oxidative carboxylate-directed ortho-homocoupling of various aromatic acids with a current efficiency of 67%. The protocol is operationally simple, tolerates a wide variety of functional groups, and does not require the exclusion of air and moisture. Heterodimerizations via cross-dehydrogenative couplings of naphthyl-1-carboxylic acids with acrylic or benzoic acids were also shown to work.

Merging C-H Activation and Strain-Release in Ruthenium-Catalyzed Isoindolinone Synthesis

The merger of strain-release of 1,2-oxazetidines with carboxylic acid directed C-H activation in catalytic synthesis of isoindolinones is reported for the first time. This reaction opens a new and sustainable avenue to prepare a range of structurally dive

Late-Stage Amination of Drug-Like Benzoic Acids: Access to Anilines and Drug Conjugates through Directed Iridium-Catalyzed C?H Activation

The functionalization of C?H bonds, ubiquitous in drugs and drug-like molecules, represents an important synthetic strategy with the potential to streamline the drug-discovery process. Late-stage aromatic C?N bond–forming reactions are highly desirable, but despite their significance, accessing aminated analogues through direct and selective amination of C?H bonds remains a challenging goal. The method presented herein enables the amination of a wide array of benzoic acids with high selectivity. The robustness of the system is manifested by the large number of functional groups tolerated, which allowed the amination of a diverse array of marketed drugs and drug-like molecules. Furthermore, the introduction of a synthetic handle enabled expeditious access to targeted drug-delivery conjugates, PROTACs, and probes for chemical biology. This rapid access to valuable analogues, combined with operational simplicity and applicability to high-throughput experimentation has the potential to aid and considerably accelerate drug discovery.