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Relevant academic research and scientific papers

Trimethylammonium-containing rhodacarborane [(9-NMe3-7,8-C2B9H10)RhCl2]2 as a catalyst for the annulation of arylcarboxylic acids with alkynes

Rhodacarborane [(9-NMe3-7,8-C2B9H10)RhCl2]2 exhibited moderate catalytic activity in the reaction of annulation of arylcarboxylic acids with alkynes, giving naphthalenes as the major produc

Effect of Cp-Ligand Methylation on Rhodium(III)-Catalyzed Annulations of Aromatic Carboxylic Acids with Alkynes: Synthesis of Isocoumarins and PAHs for Organic Light-Emitting Devices

An efficient protocol was developed for the synthesis of π-extended isocoumarins and polycyclic aromatic hydrocarbons based on the oxidative coupling of aromatic carboxylic acids with internal alkynes catalyzed by (cyclopentadienyl)rhodium complexes. The

Rhodaelectrocatalysis for Annulative C?H Activation: Polycyclic Aromatic Hydrocarbons through Versatile Double Electrocatalysis

Rapid access to structurally diversified polycyclic aromatic hydrocarbons (PAHs) in a controlled manner is of key significance in materials sciences. Herein, we describe a strategy featuring two distinct electrocatalytic C?H transformations for the synthesis of novel nonplanar PAHs. The combination of rhodaelectrooxidative C?H activation/[2+2+2] alkyne annulation of easily accessible boronic acids with electrocatalytic cyclodehydrogenation provided modular access to diversely substituted PAHs with electricity as a sustainable oxidant. The unique molecular topology as well as the photophysical and electronic properties of the thus obtained PAHs were fully analyzed. The unique power of this metallaelectrocatalysis method was demonstrated by the chemoselective assembly of synthetically useful iodo-substituted PAHs.

Room Temperature Decarboxylative and Oxidative [2+2+2] Annulation of Benzoic Acids with Alkynes Catalyzed by an Electron-Deficient Rhodium(III) Complex

It has been established that an electron-deficient (η5-cyclopentadienyl)rhodium(III) [CpERhIII] complex is capable of catalyzing the decarboxylative and oxidative [2+2+2] annulation of benzoic acids with alkynes to produce substituted naphthalenes at room temperature. The appropriate choice of the additive and the solvent is crucial for this transformation. This catalyst system allowed use of oxygen as a terminal oxidant and broadened the substrate scope including both aromatic and aliphatic alkynes. In this catalysis, the electron deficient nature of the CpERhIII catalyst would cause the strong rhodium-π interaction, which accelerates the decarboxylation as well as the C?H bond cleavage.

A decarboxylative approach for regioselective hydroarylation of alkynes

Regioselective activation of aromatic C-H bonds is a long-standing challenge for arene functionalization reactions such as the hydroarylation of alkynes. One possible solution is to employ a removable directing group that activates one of several aromatic C-H bonds. Here we report a new catalytic method for regioselective alkyne hydroarylation with benzoic acid derivatives during which the carboxylate functionality directs the alkyne to the ortho-C-H bond with elimination in situ to form a vinylarene product. The decarboxylation stage of this tandem sequence is envisioned to proceed with the assistance of an ortho-alkenyl moiety, which is formed by the initial alkyne coupling. This ruthenium-catalysed decarboxylative alkyne hydroarylation eliminates the common need for pre-existing ortho-substitution on benzoic acids for substrate activation, proceeds under redox-neutral and relatively mild conditions, and tolerates a broad range of synthetically useful aromatic functionality. Thus, it significantly increases the synthetic utility of benzoic acids as easily accessible aromatic building blocks.

Synthesis of highly substituted acenes through rhodium-catalyzed oxidative coupling of arylboron reagents with alkynes

The rhodium-catalyzed oxidative 1:2 coupling reactions of arylboronic acids or their esters with alkynes smoothly proceed to produce the corresponding annulated products. Of special note, highly substituted, readily soluble, and tractable anthracene and tetracene derivatives can be obtained selectively from 2-naphthyl- and 2-anthrylboron reagents, respectively.

Synthesis of highly substituted naphthalene and anthracene derivatives by rhodium-catalyzed oxidative coupling of arylboronic acids with alkynes

The rhodium-catalyzed oxidative 1:2 coupling reactions of arylboronic acids with alkynes effectively proceeds in the presence of a copper-air oxidant to produce the corresponding annulated products. Of special note, anthracene derivatives can be obtained

Rhodium-catalyzed oxidative coupling of triarylmethanols with internal alkynes via successive C-H and C-C bond cleavages

(Chemical Equation Presented) The rhodium-catalyzed oxidative coupling of triarylmethanols with internal alkynes effectively proceeds in a 1:2 manner via cleavage of C-H and C-C bonds to produce the corresponding naphthalene derivatives. Addition of trior tetraphenylcyclopentadiene as a ligand is crucial for the reaction to occur efficiently.

Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes via regioselective C-H bond cleavage

(Chemical Equation Presented) The oxidative coupling of benzoic acids with internal alkynes effectively proceeds in the presence of [Cp*RhCl 2]2 and Cu(OAc)2·H2O as catalyst and oxidant, respectively, to produce