Well-dispersed palladium(0) nanoparticles with small and narrow size distributions were synthesized conveniently on a graphene oxide (GO) surface. The GO-supported nano-Pd(0) was found to be a highly efficient and recyclable catalyst for the carbonylative cross-coupling reaction between arylboronic acids and aryl and carboranyl iodides, respectively. Benzophenone and a series of carboranylaryl ketones, 1-R-2-[C(=O)Ar]-1,2-C2B10H10 (R = H, Me, Ph; Ar = C6H5, C6H4-4-OMe and C6H4-4-F), were synthesized and fully characterized. The catalyst was recyclable at least three times with sustained activity.

Download full-text PDF

Source
http://dx.doi.org/10.1039/c3dt52560kDOI Listing

Publication Analysis

Top Keywords

cross-coupling reaction
8
reaction arylboronic
8
arylboronic acids
8
carboranyl iodides
8
graphene oxide
8
carboranylaryl ketones
8
acids carboranyl
4
iodides catalyzed
4
catalyzed graphene
4
oxide go-supported
4

Similar Publications

This work explores the use of a cross-shaped organic framework that is used as a template for the investigation of multi-functionalized chromophores. We report the design and synthesis of a universal cross-shaped building block bearing two bromines and two iodines on its peripheral positions. The template can be synthesized on a gram scale in a five-step reaction comprising an oxidative homo-coupling macro-cyclization.

View Article and Find Full Text PDF

High-throughput chemistry (HTC) and direct-to-biology (D2B) platforms allow for plate-based compound synthesis and biological evaluation of crude mixtures in cellular assays. The rise of these workflows has rapidly accelerated drug-discovery programs in the field of targeted protein degradation (TPD) in recent years by removing a key bottleneck of compound purification. However, the number of chemical transformations amenable to this methodology remain minimal, leading to limitations in the exploration of chemical space using existing library-based approaches.

View Article and Find Full Text PDF

General access to furan-substituted -difluoroalkenes enabled by PFTB-promoted cross-coupling of ene-yne-ketones and difluorocarbene.

Chem Sci

December 2024

Department of Spine Surgery and Musculoskeletal Tumor, Zhongnan Hospital of Wuhan University, School of Pharmaceutical Sciences, Wuhan University Wuhan 430071 China

Replacement of a carbonyl group with fluorinated bioisostere (, CF[double bond, length as m-dash]C) has been adopted as a key tactical strategy in drug design and development, which typically improves potency and modulates lipophilicity while maintaining biological activity. Consequently, new -difluoroalkenation reactions have undoubtedly accelerated this shift, and conceptually innovative practices would be of great benefit to medicinal chemists. Here we describe an expeditous protocol for the direct assembly of furan-substituted -difluoroalkenes PFTB-promoted cross-coupling of ene-yne-ketones and difluorocarbene.

View Article and Find Full Text PDF

We describe herein the design and synthesis of a new class of dialkylarylphosphine ligands incorporating a Lewis-basic urea subunit. The ligand synthesis consisted of six linear steps and was enabled by the discovery of a new N-to-N alkyl migration reaction. This new series of dialkylarylphosphine urea ligands were applied in common palladium-catalyzed cross-coupling reactions for the formation of carbon-carbon and carbon-nitrogen bonds in moderate to high yields.

View Article and Find Full Text PDF

Nickel-catalyzed cross-electrophile coupling (XEC) reactions of (hetero)aryl electrophiles represent appealing alternatives to palladium-catalyzed methods for biaryl synthesis, but they often generate significant quantities of homocoupling and/or proto-dehalogenation side products. In this study, an informer library of heteroaryl chloride and aryl bromide coupling partners is used to identify Ni-catalyzed XEC conditions that access high selectivity for the cross-product when using equimolar quantities of the two substrates. Two different catalyst systems are identified that show complementary scope and broad functional-group tolerance, and time-course data suggest that the two methods follow different mechanisms.

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!