Rhodium Catalyzed Arylation of Diazo Compounds with Aryl Boronic Acids

Abstract

A general and efficient synthesis of diarylacetate, a diarylmethine derivative, was accomplished through rhodium catalyzed direct arylation of diazo compounds with arylboronic acids. The reaction tolerates various boronic acid derivatives and functional groups. Notably, chemoselective arylation of diazo compounds over other electrophiles were demonstrated. The efficacy of the developed methodology is shown by the expeditious synthesis of the core structure of diclofensine.

Metal‐Free Tandem Rearrangement/Lactonization: Access to 3,3‐Disubstituted Benzofuran‐2‐(3H)‐ones

“…Developed by Hoffmann-La Roche,d iclofensine is an antidepressant drug containing ad ichloroarene-substituted tetrahydroisoquinoline. [24] Interestingly,w hen attempting the borane-mediated arylation of 2-benzyloxy-substituted diazo derivative 2g with boranes 1d or 1e,lactones 4a and 4b resulted, as determined by single-crystal X-ray diffraction (Scheme 3a nd the Supporting Information). As expected, the reaction of 1fwith 2eled to the formation of 3pin 92 %yield.…”

Ligand‐based Modeling for the Prediction of Pharmacophore Features for Multi‐targeted Inhibition of the Arachidonic Acid Cascade

“…The compounds N‐(2‐(1H‐Indol‐3‐yl)‐2‐phenylethyl)‐4‐methylbenzenesulfonamide ( C1 ) and 2‐(3,4‐dichlorophenyl)‐2(4‐methoxyphenyl)ethanol ( C2 ) were synthesised and their inhibition of the formation of prostaglandin E2, product of mPGES‐1, was estimated as described previously . Hela cells were cultured in Dulbecco's Modified Essential Medium supplemented with 10 % Fetal bovine serum under 5 % CO2.…”

“…The compounds N-(2-(1H-Indol-3-yl)-2-phenylethyl)-4-methylbenzenesulfonamide (C1) and 2-(3,4-dichlorophenyl)-2(4methoxyphenyl)ethanol (C2) were synthesised and their inhibition of the formation of prostaglandin E2, product of mPGES-1, was estimated as described previously. [34][35][36] Hela cells were cultured in Dulbecco's Modified Essential Medium supplemented with 10 % Fetal bovine serum under 5 % CO2. The cells were pretreated with compounds (50 mM), Licofelone (5 mM, positive control) or DMSO (control) for 2 hours and then induced with TNFa (50 ng/ml) for 24 hours.…”

Metallfreie Tandem‐Umlagerung/Lactonisierung: Zugang zu 3,3‐disubstituierten Benzofuran‐2‐(3H)‐onen

“…Der Einbau von Mono-oder Polyhalogenarylfunktionen, wie sie in 3f-o erzeugt werden, ist fürdie pharmazeutische, [21] agrochemische und elektronische Industrie von grçßter Bedeutung. [24] Beim Versuch der Boran-vermittelten Arylierung des 2-Benzyloxy-substituierten Diazoderivats 2g mit Boranen 1d oder 1e resultierten Lactone 4a bzw. Diclofensin ist ein von Hoffmann-La Roche entwickeltes Antidepressivum, das ein Te trahydroisochinolin, substituiert mit einem Dichloraren, enthält.…”