3611-72-1

Usage

InChI:InChI=1/C15H11ClO2/c16-12-7-5-10(6-8-12)15(17)14-9-11-3-1-2-4-13(11)18-14/h1-9,15,17H

Upstream product

• 27052-20-6 (1-benzofuran-2-yl)(4-chlorophenyl)methanone 
• 271-89-6 1-benzofurane 
• 104-88-1 4-chlorobenzaldehyde 
• 637-87-6 1-Chloro-4-iodobenzene 
• 4265-16-1 2-formylbenzo[b]furan 
• 90-02-8 salicylaldehyde 
• 536-38-9 4-chlorobenzoylmethyl bromide 

Relevant academic research and scientific papers

Catalytic Aldehyde and Alcohol Arylation Reactions Facilitated by a 1,5-Diaza-3,7-diphosphacyclooctane Ligand

We report a catalytic method to access secondary alcohols by the coupling of aryl iodides. Either aldehydes or alcohols can be used as reaction partners, making the transformation reductive or redox-neutral, respectively. The reaction is mediated by a Ni catalyst and a 1,5-diaza-3,7-diphosphacyclooctane. This P2N2ligand, which has previously been unrecognized in cross-coupling and related reactions, was found to avoid deleterious aryl halide reduction pathways that dominate with more traditional phosphines and NHCs. An interrupted carbonyl-Heck type mechanism is proposed to be operative, with a key 1,2-insertion step forging the new C-C bond and forming a nickel alkoxide that may be turned over by an alcohol reductant. The same catalyst was also found to enable synthesis of ketone products from either aldehydes or alcohols, demonstrating control over the oxidation state of both the starting materials and products.

Enantioselective reduction of benzofuranyl aryl ketones

Enantioselective transfer hydrogenation of benzofuranyl aryl ketones proceeds with moderate to good enantioselectivity even when the aryl group is not sterically differentiated by ortho-substituents. The best results are obtained with substrates that are functionalised by electron-withdrawing aryl groups that contrast with the electron-rich benzofuran, which is consistent with [Ru-ArC-H]·Ar π interactions acting as a control element. Enantioselective pressure hydrogenation gives lower enantioselectivity irrespective of electronic effects, unless the aryl group is ortho-substituted, in which case up to 86% ee can be realised. Georg Thieme Verlag Stuttgart - New York.

Deprotonation of furans using lithium magnesates

Furan was deprotonated on treatment with 1/3 equiv of Bu3MgLi in THF at rt. The lithium arylmagnesate formed was either trapped with electrophiles or involved in a palladium-catalyzed cross-coupling reaction with 2-bromopyridine. The highly coordinated magnesate Bu4MgLi2 (1/3 equiv) proved to be a better deprotonating agent than Bu3MgLi; the monitoring of the reaction using NMR spectroscopy showed that the deprotonation of furan at rt required 2 h whereas the subsequent electrophilic trapping was instantaneous. The method was extended to benzofuran, allowing its functionalization at C2 in high yields. The deprotonation of 2-methylfuran and lithium furfurylalkoxide at C5 turned out to be difficult, requiring either long reaction times or higher temperatures.

1-[(benzofuran-2-yl)phenylmethyl]-triazoles and -tetrazoles - Potent competitive inhibitors of aromatase

The synthesis of a series of novel 1-[(benzofuran-2-yl)phenylmethyl]- triazoles and -tetrazoles is described. The compounds were tested for human placental aromatase inhibition in vitro, using [1β-3H]androstenedione as the substrate for the aromatase enzyme, the percentage inhibition and IC50 data is included.