Photoinduced arylation of chloroarenes in flow: synthesis of unsymmetrical biaryls.

Org Biomol Chem

Department of Applied Chemistry, National Yang Ming Chiao Tung University, 1001 University Road, Hsinchu 30010, Taiwan.

Published: November 2022

A photoflow method is presented for a radical-based coupling of unactivated arenes and aryl chlorides. The process proceeded smoothly at ambient temperature under metal-free conditions. Of note is that the reaction conditions are fine-tuned for chloroarenes with different electronic properties. While the reactivity profile of aryl chlorides is generally known to be inferior to those of the corresponding iodides and bromides, we demonstrate that the title protocol is efficient in converting readily available and inexpensive chloroarenes into unsymmetrical biaryl products.

Download full-text PDF

Source
http://dx.doi.org/10.1039/d2ob01710eDOI Listing

Publication Analysis

Top Keywords

aryl chlorides
8
photoinduced arylation
4
arylation chloroarenes
4
chloroarenes flow
4
flow synthesis
4
synthesis unsymmetrical
4
unsymmetrical biaryls
4
biaryls photoflow
4
photoflow method
4
method presented
4

Similar Publications

Preformed Ni(0) complexes are rarely used as precatalysts in cross-coupling reactions, although they can incorporate catalytically active nickel directly into the reaction. In this work, we focus on the preparation and the catalytic application of low-coordinate Ni(0) complexes supported by bulky monophosphine ligands in C-S cross-coupling reactions. We have prepared two families of Ni(0) complexes, bis-phosphine aducts of the type [Ni(PRAr')] (Ar' = -terphenyl group) and monophosphine derivatives of the type [Ni(PRAr')(DVDS)] (DVDS = divinyltetramethyldisiloxane).

View Article and Find Full Text PDF

Buchwald-Hartwig (BH) aminations are crucial for synthesizing arylamine motifs in numerous bioactive molecules and fine chemicals. While homogeneous palladium complexes can be effective catalysts, their high costs and environmental impact motivate the search for alternative approaches. Heterogeneous palladium single-atom catalysts (SAC) offer promising recoverable alternatives in C-C cross-couplings.

View Article and Find Full Text PDF

Visible-Light-Triggered Mn(CO)-Catalyzed Carbonylation of (Hetero)aryl Chlorides.

Org Lett

January 2025

Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.

Carbonylation of aryl electrophiles is an important method for constructing aromatic carbonyl compounds for materials science and pharmaceutical applications. However, there have been few studies on the carbonylation of abundant, inexpensive aryl chlorides. Moreover, the existing carbonylation methods usually require a high temperature, control of the CO pressure, and structurally complex catalysts and ligands.

View Article and Find Full Text PDF

Palladium-catalyzed -arylation of (hetero)aryl chlorides with pyrroles and their analogues.

Org Biomol Chem

January 2025

School of Chemistry and Chemical Engineering, Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, Guangxi University, Nanning 530004, Guangxi, P. R. China.

We present a mild and efficient method for the arylation of N-H heteroarenes using a low-loading Pd/keYPhos catalyst (0.8 mol%). This approach employs inexpensive and structurally diverse aryl chlorides as electrophiles in reactions with indoles, pyrroles, and carbazole, enabling the construction of a wide range of -arylated products.

View Article and Find Full Text PDF

The development of new protocols for stereospecific and stereoselective halogenation transformations by mild reaction conditions is a highly desirable research target for the chemical and pharmaceutical industries. Following the straightforward methodology for directly transforming a wide scope of alcohols to alkyl bromides and chlorides using substoichiometric amounts of thioureas and N-halo succinimides (NXS) as a halogen source in a single step, we noticed that in apolar solvents bromination of chiral secondary alcohols did not produce the expected racemates. In this study, the stereochemical aspects of the bromination reaction were examined.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!